SecProbe.io

CORRESP
 1
 filename1.htm

 FOXO
TECHNOLOGIES INC.

 477
South Rosemary Avenue

 Suite
224

 West
Palm Beach, FL 33401

 June
5, 2025

 VIA
EDGAR

 Division
of Corporation Finance

 Office
of Industrial Applications and Services

 Securities
and Exchange Commission

 Washington,
DC 20549

 Attention:
Ms. Sawicki

 Re:
 FOXO
 Technologies Inc.

 Registration
 Statement on Form S-1

 SEC
 File No. 333-287818

 Ladies
and Gentlemen:

 Pursuant
to Rule 461 under the Securities Act of 1933, as amended, the undersigned, on behalf of FOXO Technologies Inc., a Delaware corporation
(the " Issuer "), respectfully requests that the effective date of the Registration Statement on Form S-1 referenced
above be accelerated so that it will become effective at 5:15 P.M., Eastern Time, on June 9, 2025, or as soon as practicable thereafter.

 There
are no underwriters in connection with the registration and, therefore, no request for acceleration or consent by an underwriter has
been filed herewith.

 The
Issuer hereby authorizes Brian Higley of Business Legal Advisors, LLC to orally modify or withdraw this request for acceleration. If
you have any questions regarding the foregoing, please contact Mr. Higley at (801) 634-1984 or by e-mail ( brian@businesslegaladvisor.com ).

 Thank
you in advance for your assistance.

 Very
truly yours,

 FOXO
 Technologies Inc.

 By:
 /s/
 Seamus Lagan

 Name:
 Seamus
 Lagan

 Title:
 CEO

 cc:
Brian Higley, Esq., Business Legal Advisors, LLC

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 June 3, 2025

Seamus Lagan
Chief Executive Officer
FOXO Technologies Inc.
477 South Rosemary Avenue
Suite 224
West Palm Beach, FL 33401

 Re: FOXO Technologies Inc.
 Draft Registration Statement on Form S-1
 Submitted May 28, 2025
 CIK No. 0001812360
Dear Seamus Lagan:

 This is to advise you that we do not intend to review your registration
statement.

 We request that you publicly file your registration statement at least
two business
days prior to the requested effective date and time. Please refer to Rules 460
and 461
regarding requests for acceleration. We remind you that the company and its
management are
responsible for the accuracy and adequacy of their disclosures, notwithstanding
any review,
comments, action or absence of action by the staff.

 Please contact Margaret Sawicki at 202-551-7153 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of
Industrial Applications and
 Services
cc: Brian Higley, Esq.
</TEXT>
</DOCUMENT>

CORRESP
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 filename1.htm

 FOXO
TECHNOLOGIES INC.

 477
South Rosemary Avenue

 Suite
224

 West
Palm Beach, FL 33401

 May
2, 2025

 VIA
EDGAR

 Division
of Corporation Finance

 Office
of Industrial Applications and Services

 Securities
and Exchange Commission

 Washington,
DC 20549

 Attention:
Ms. Sawicki

 Re:
 FOXO
Technologies Inc.

 Registration
Statement on Form S-1

 SEC
File No. 333-286953

 Ladies
and Gentlemen:

 Pursuant
to Rule 461 under the Securities Act of 1933, as amended, the undersigned, on behalf of FOXO Technologies Inc., a Delaware corporation
(the " Issuer "), respectfully requests that the effective date of the Registration Statement on Form S-1 referenced
above be accelerated so that it will become effective at 4:00 P.M., Eastern Time, on May 6, 2025, or as soon as practicable thereafter.

 There
are no underwriters in connection with the registration and, therefore, no request for acceleration or consent by an underwriter has
been filed herewith.

 The
Issuer hereby authorizes Brian Higley of Business Legal Advisors, LLC to orally modify or withdraw this request for acceleration. If
you have any questions regarding the foregoing, please contact Mr. Higley at (801) 634-1984 or by e-mail ( brian@businesslegaladvisor.com ).

 Thank
you in advance for your assistance.

 Very
truly yours,

 FOXO
 Technologies Inc.

 By:
 /s/ Seamus Lagan

 Name:
 Seamus Lagan

 Title:
 CEO

 cc:
Brian Higley, Esq., Business Legal Advisors, LLC

<DOCUMENT>
<TYPE>TEXT-EXTRACT
<SEQUENCE>2
<FILENAME>filename2.txt
<TEXT>
 April 30, 2025

Seamus Lagan
Chief Executive Officer
FOXO Technologies Inc.
477 South Rosemary Avenue
Suite 224
West Palm Beach, FL 33401

 Re: FOXO Technologies Inc.
 Draft Registration Statement on Form S-1
 Submitted April 24, 2025
 CIK No. 0001812360
Dear Seamus Lagan:

 This is to advise you that we do not intend to review your registration
statement.

 We request that you publicly file your registration statement at least
two business
days prior to the requested effective date and time. Please refer to Rules 460
and 461
regarding requests for acceleration. We remind you that the company and its
management are
responsible for the accuracy and adequacy of their disclosures, notwithstanding
any review,
comments, action or absence of action by the staff.

 Please contact Margaret Sawicki at 202-551-7153 with any questions.

 Sincerely,

 Division of
Corporation Finance
 Office of
Industrial Applications and
 Services
cc: Brian Higley, Esq.
</TEXT>
</DOCUMENT>

January 7, 2025
Seamus Lagan
Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, MN 55401
Re:FOXO Technologies Inc.
Amendment No. 2 to Preliminary Proxy Statement on Schedule 14A
Filed January 3, 2025
File No. 001-39783
Dear Seamus Lagan:
            We have completed our review of your filing. We remind you that the company and
its management are responsible for the accuracy and adequacy of their disclosures,
notwithstanding any review, comments, action or absence of action by the staff.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:J. Thomas Cookson, Esq.

CORRESP
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  J.
                         Thomas Cookson

Partner

Shutts
& Bowen LLP

200
South Biscayne Boulevard

Suite 4100

Miami, FL 33131

DIRECT
(305) 379-9141

EMAIL
TCookson@shutts.com

January
3, 2025

VIA
EDGAR

Jane
Park

United
States Securities and Exchange Commission

100
F Street

Washington,
D.C. 20549

  Re:
  FOXO Technologies Inc.

  Amendment No. 1 to Preliminary
  Proxy Statement on Schedule 14A

  Filed December 13, 2024

  File No. 001-39783

Dear
Ms. Park:

On
behalf of FOXO Technologies Inc., a Delaware corporation (the “Company”), we hereby are filing Amendment No. 2 to the Preliminary
Proxy Statement on Schedule 14A. Please note that the proxy statement now relates to a special meeting of stockholders. The Company intends
to file the definitive proxy statement early next week.

If
you have any questions, please contact me at (305) 379-9141. Thank you for your assistance and Happy New Year.

    Very
    truly yours,

    Shutts
    & Bowen LLP

    /s/
    J. Thomas Cookson

    J.
    Thomas Cookson

JC:/ieb

  cc:
  Seamus Lagan

  FOXO Technologies Inc.

CORRESP
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December
13, 2024

VIA
EDGAR

Jane
Park

United
States Securities and Exchange Commission

100
F Street

Washington,
D.C. 20549

    Re:
    FOXO
    Technologies Inc.

    Preliminary
    Proxy Statement on Schedule 14A

    Filed
    July 31, 2024

    File
    No. 001-39783

Dear
Ms. Park:

On
behalf of FOXO Technologies Inc., a Delaware corporation (the “Company”), we hereby respond to the Staff’s comment
letter, dated August 7, 2024, regarding the Company’s Preliminary Proxy Statement on Schedule 14A filed on July 31, 2024. Please
note that for the Staff’s convenience, we have recited the Staff’s comment in hold face type and provided the Company’s
response immediately thereafter. Please also note that we are simultaneously filing Amendment No. 1 to the Preliminary Proxy Statement
on Schedule 14A.

Preliminary
Proxy Statement on Schedule 14A filed July 31, 2024.

General

1.
We note that Proposal 5 of your proxy statement seeks the authorization of the issuance of 20% or more of your outstanding common
stock in connection with the acquisition of Myrtle Recovery Centers, Inc. We also note that you are seeking stockholder approval of the
potential issuance of shares of common stock in connection with the acquisition of Rennova Community Health, Inc. pursuant to Proposal
6 of your proxy statement. As it appears that Proposals 5 and 6 involve solicitations of your shareholders for the purpose of issuing
additional shares which are to be used to acquire other specified companies, and your shareholders will not have separate opportunities
to vote upon these transactions, please revise your disclosure to provide the information required by Note A of Schedule 14A for each
proposal, including the information set forth in Items 11, 13 and 14 of Schedule 14A, or provide us your analysis why this information
is not required. When providing this disclosure, please include the amount of securities to be issued, all audited and pro forma financial
information required by Items 13 and 14 of Schedule 14A, and all transaction-related information required by Item 14 of Schedule 14A.
Additionally, please file the amended proxy statement with the PREM14A EDGAR tag and ensure that any subsequent proxy statement filings
are properly designated.

 Please
note that the proposals to be considered at the Annual Meeting have been revised so that the Company is no longer seeking approval for
proposals relating to the acquisition of other specified companies. In the case of each of Myrtle and RCHI, the agreements to acquire
the entities have closed and each is already a subsidiary of the Company. As a result, the Company respectfully believes that the changes
in the proposals remove the issues raised by the prior comment.

If
you have any questions, please contact me at (305) 379-9141.

    Very
    truly yours,

    J.
    Thomas Cookson

    Cc:
    Abby
    Adams

    Securities
    and Exchange Commission

    Seamus
    Lagan

    FOXO
    Technologies Inc.

August 7, 2024
Mark White
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, MN 55401
Re:FOXO Technologies Inc.
Preliminary Proxy Statement on Schedule 14A
Filed July 31, 2024
File No. 001-39783
Dear Mark White:
            We have reviewed your filing and have the following comment.
            Please respond to this letter within ten business days by providing the requested
information or advise us as soon as possible when you will respond. If you do not believe a
comment applies to your facts and circumstances, please tell us why in your response.
            After reviewing your response to this letter, we may have additional comments.
Preliminary Proxy Statement on Schedule 14A filed July 31, 2024
General
We note that Proposal 5 of your proxy statement seeks the authorization of the issuance of
20% or more of your outstanding common stock in connection with the acquisition of
Myrtle Recovery Centers, Inc. We also note that you are seeking stockholder approval of
the potential issuance of shares of common stock in connection with the acquisition of
Rennova Community Health, Inc. pursuant to Proposal 6 of your proxy statement. As it
appears that Proposals 5 and 6 involve solicitations of your shareholders for the purpose
of issuing additional shares which are to be used to acquire other specified companies,
and your shareholders will not have separate opportunities to vote upon these transactions,
please revise your disclosure to provide the information required by Note A of Schedule
14A for each proposal, including the information set forth in Items 11, 13 and 14 of
Schedule 14A, or provide us your analysis why this information is not required. When
providing this disclosure, please include the amount of securities to be issued, all audited
and pro forma financial information required by Items 13 and 14 of Schedule 14A, and all
transaction-related information required by Item 14 of Schedule 14A. Additionally, please
file the amended proxy statement with the PREM14A EDGAR tag and ensure that any 1.

August 7, 2024
Page 2
subsequent proxy statement filings are properly designated.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Please contact Jane Park at 202-551-7439 or Abby Adams at 202-551-6902 with any
other questions.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:Brian Higley, Esq.

CORRESP
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FOXO Technologies Inc.

October 25, 2023

VIA EDGAR

U.S. Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

    RE:
    FOXO Technologies Inc.

Registration Statement on Form S-1

Filed October 18, 2023, as amended

File No. 333-275072

Acceleration Request

Requested Date: Friday, October 27, 2023

Requested Time: 4:30 p.m. Eastern Time

Ladies and Gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”) hereby requests that the
Securities and Exchange Commission (the “Commission”) take appropriate action to cause the above-referenced Registration
Statement on Form S-1 (File No. 333-275072) (the “Registration Statement”) to become effective on Friday, October 27,
2023, at 4:30 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant or its outside counsel, Mitchell
Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once the Registration Statement
has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron at (917) 546-7709.

    Very truly yours,

    FOXO Technologies Inc.

    By:
    /s/ Mark White

    Mark White

    Interim Chief Executive Officer

FOXO Technologies Inc. – 729 N. Washington
Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

United States securities and exchange commission logo
October 25, 2023
Mark White
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, Minnesota 55401
Re:FOXO Technologies Inc.
Registration Statement on Form S-1
Filed October 18, 2023
File No. 333-275072
Dear Mark White:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration. We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Juan Grana at 202-551-6034 with any questions.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:       Blake Baron, Esq.

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FOXO Technologies Inc.

September 5, 2023

VIA EDGAR

U.S. Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

    RE:
    FOXO Technologies Inc.

Registration Statement on Form S-1

Filed August 25, 2023, as amended

File No. 333-274221

Acceleration Request

Requested Date: Wednesday, September 6, 2023

Requested Time: 5:00 p.m. Eastern Time

Ladies and Gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”) hereby requests that the
Securities and Exchange Commission (the “Commission”) take appropriate action to cause the above-referenced Registration
Statement on Form S-1 (File No. 333-274221) (the “Registration Statement”) to become effective on Wednesday, September
6, 2023, at 5:00 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant or its outside counsel,
Mitchell Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once the Registration Statement
has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron at (917) 546-7709.

    Very truly yours,

    FOXO Technologies Inc.

    By:
    /s/ Tyler Danielson

    Tyler Danielson

    Interim Chief Executive Officer

FOXO Technologies Inc. – 729 N. Washington
Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

United States securities and exchange commission logo
September 1, 2023
Tyler Danielson
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, Minnesota 55401
Re:FOXO Technologies Inc.
Registration Statement on Form S-1
Filed August 25, 2023
File No. 333-274221
Dear Tyler Danielson:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Jane Park at 202-551-7439 with any questions.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:       Blake Baron, Esq.

CORRESP
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FOXO
Technologies Inc.

August
1, 2023

VIA
EDGAR

U.S.
Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

    RE:
    FOXO
    Technologies Inc.

Registration
Statement on Form S-1

Filed
July 21, 2023, as amended

File
No. 	333-273377

Acceleration
Request

Requested
Date: Thursday, August 3, 2023

Requested
Time: 4:30 p.m. Eastern Time

Ladies
and Gentlemen:

In
accordance with Rule 461 under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”)
hereby requests that the Securities and Exchange Commission (the “Commission”) take appropriate action to cause the
above-referenced Registration Statement on Form S-1 (File No. 333-273377) (the “Registration Statement”) to become
effective on Thursday, August 3, 2023, at 4:30 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant
or its outside counsel, Mitchell Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once
the Registration Statement has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron
at (917) 546-7709.

    Very truly yours,

    FOXO Technologies Inc.

    By:
    /s/ Tyler
    Danielson

    Tyler Danielson

    Interim Chief Executive Officer

FOXO
Technologies Inc. – 729 N. Washington Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

United States securities and exchange commission logo
July 28, 2023
Tyler Danielson
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, Minnesota 55401
Re:FOXO Technologies Inc.
Registration Statement on Form S-1
Filed July 21, 2023
File No. 333-273377
Dear Tyler Danielson:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Benjamin Richie at 202-551-7857 with any questions.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:       Blake Baron

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FOXO Technologies Inc.

July 3, 2023

VIA EDGAR

U.S. Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

    RE:
    FOXO Technologies Inc.

Registration Statement on Form S-1

Filed June 23, 2023

File No. 333-272892

Acceleration Request

Requested Date: Thursday, July 6, 2023

Requested Time: 5:00 p.m. Eastern Time

Ladies and Gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”) hereby requests that the
Securities and Exchange Commission (the “Commission”) take appropriate action to cause the above-referenced Registration
Statement on Form S-1 (File No. 333-272892) (the “Registration Statement”) to become effective on Thursday, July 6,
2023, at 5:00 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant or its outside counsel, Mitchell
Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once the Registration Statement
has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron at (917) 546-7709.

    Very truly yours,

    FOXO Technologies Inc.

    By:
    /s/ Tyler Danielson

    Tyler Danielson

    Interim Chief Executive Officer

FOXO Technologies Inc. – 729 N. Washington
Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

United States securities and exchange commission logo
July 3, 2023
Tyler Danielson
Interim Chief Executive Officer
FOXO TECHNOLOGIES INC.
729 N. Washington Ave., Suite 600
Minneapolis, Minnesota 55401
Re:FOXO TECHNOLOGIES INC.
Registration Statement on Form S-1
Filed June 23, 2023
File No. 333-272892
Dear Tyler Danielson:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Margaret Schwartz at 202-551-7153 with any questions.
Sincerely,
Division of Corporation Finance
Office of Industrial Applications and
Services
cc:       Blake Baron, Esq.

CORRESP
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May 5, 2023

Division of Corporation Finance

Office of Mergers & Acquisitions

Attention: Daniel Duchovny 202-551-3619

Re: FOXO Technologies Inc.

Schedule TO-I (PIK Notes) (the “Schedule TO”)

Submitted April 27, 2023

File No. 005-91932

Dear Mr. Duchovny:

FOXO Technologies Inc. (the “Company”)
confirms receipt of the letter dated May 3, 2023 from the staff (the “Staff”) of the Securities and Exchange Commission
(the “Commission”) with respect to the above-referenced filing. We are responding to the Staff’s comment as set
forth below.

Concurrently with the submission of this response
letter, we are filing, through EDGAR, Amendment No. 1 to the Schedule TO (“Amendment No. 1”). Unless otherwise indicated,
capitalized terms used herein have the meanings assigned to them in Amendment No. 1. The Staff’s comment is set forth below in bold,
followed by the Company’s response:

Schedule TO-I (PIK Notes)

Offer to Amend -- The Offer -- Financial Information Regarding
the Company, page 18

 1. It appears, based on the response to Item 10 of the Schedule TO, that Foxo financial information disclosure has been incorporated
by reference to satisfy that item requirement. Revise to include the complete summarized financial information required by Item 1010(c)
of Regulation M-A.

RESPONSE: In response to the Staff’s comment, the Company
has revised the Offer Letter to provide the summary financial information required by Item 1010(c) of Regulation M-A on page 18 thereof.

***

We trust that this response satisfactorily responds to your request.
Should you require further information, please contact our legal counsel Blake Baron at (917) 546-7709.

    Sincerely,

    /s/ Tyler Danielson

    Tyler Danielson,

    Interim Chief Executive Officer

CORRESP
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May 5, 2023

Division of Corporation Finance

Office of Mergers & Acquisitions

Attention: Daniel Duchovny 202-551-3619

Re: FOXO Technologies Inc.

Schedule TO-I (Warrants) (the “Schedule TO”)

Submitted April 27, 2023

File No. 005-91932

Dear Mr. Duchovny:

FOXO Technologies Inc. (the “Company”)
confirms receipt of the letter dated May 3, 2023 from the staff (the “Staff”) of the Securities and Exchange Commission
(the “Commission”) with respect to the above-referenced filing. We are responding to the Staff’s comment as set
forth below.

Concurrently with the submission of this response
letter, we are filing, through EDGAR, Amendment No. 1 to the Schedule TO (“Amendment No. 1”). Unless otherwise indicated,
capitalized terms used herein have the meanings assigned to them in Amendment No. 1. The Staff’s comment is set forth below in bold,
followed by the Company’s response:

Schedule TO-I (Warrants)

Offer to Exchange -- The Offer -- The Offer, page 4

 1. We note that the security holders must consent to the General Release Agreement (filed as an exhibit to the Schedule TO), which
includes very broad waivers. The General Release Agreement does not appear to comply with section 29(a) and (b) of the Securities Exchange
Act of 1934. Thus, please revise the agreement to ensure compliance with the Securities Exchange Act and include disclosure in your Offer
to Exchange that any agreements already delivered to you will be deemed to have been so modified.

RESPONSE: In response to the Staff’s comment, pursuant
to Amendment No. 1, the Company has revised the Letter of Transmittal and Consent by adding the following language to the General Release
Agreement at the end of Section 2(a) thereof:

“Notwithstanding anything else in this General Release
Agreement to the contrary, by executing this General Release Agreement (by Holder’s execution and delivery of a Letter of Transmittal
and Consent, together with any other required documents in accordance with the terms of the Offer and Consent Solicitation, electing thereby
to participate in the Offer and Consent Solicitation, pursuant to Section 4(e) hereto) Holder shall not be deemed to have waived compliance
with any provision of Securities Exchange Act of 1934 or of any rule or regulation thereunder, or of any rule of a self-regulatory
organization.”

In addition, pursuant to Amendment No. 1, the Company has revised the Offer
Letter by adding the following language on the cover page thereof:

“On May 5, 2023, the Company amended and restated the
Letter of Transmittal and Consent to modify the General Release Agreement. All consents delivered by holders of Assumed Warrants electing
to participate in the Offer prior to such date are deemed to have been so modified.”

Offer to Amend -- The Offer -- Financial Information Regarding
the Company, page 19

 2. It appears, based on the response to Item 10 of the Schedule TO, that Foxo financial information disclosure has been incorporated
by reference to satisfy that item requirement. Revise to include the complete summarized financial information required by Item 1010(c)
of Regulation M-A.

RESPONSE: In response to the Staff’s comment, the Company
has revised the Offer Letter to provide the summary financial information required by Item 1010(c) of Regulation M-A on page 19 thereof.

***

We trust that this response satisfactorily responds to your request.
Should you require further information, please contact our legal counsel Blake Baron at (917) 546-7709.

    Sincerely,

    /s/ Tyler Danielson

    Tyler Danielson,

    Interim Chief Executive Officer

CORRESP
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FOXO
Technologies Inc.

May
3, 2023

VIA
EDGAR

U.S.
Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

RE: FOXO
Technologies Inc.

Registration
Statement on Form S-1

Filed
April 27, 2023

File
No. 333-271475

Acceleration
Request

Requested
Date: Friday, May 5, 2023

Requested
Time: 5:00 p.m. Eastern Time

Ladies
and Gentlemen:

In
accordance with Rule 461 under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”)
hereby requests that the Securities and Exchange Commission (the “Commission”) take appropriate action to cause the
above-referenced Registration Statement on Form S-1 (File No. 333-271475) (the “Registration Statement”) to become
effective on Friday, May 5, 2023, at 5:00 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant
or its outside counsel, Mitchell Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once
the Registration Statement has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron
at (917) 546-7709.

    Very
    truly yours,

    FOXO
    Technologies Inc.

    By:
    /s/
    Tyler Danielson

    Tyler
    Danielson

    Interim
    Chief Executive Officer

FOXO
Technologies Inc. – 729 N. Washington Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

United States securities and exchange commission logo
May 3, 2023
Tyler Danielson
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, MN 55401
Re:FOXO Technologies Inc.
Registration Statement on Form S-1
Filed April 27, 2023
File No. 333-271475
Dear Tyler Danielson:
            This is to advise you that we have not reviewed and will not review your registration
statement.
            Please refer to Rules 460 and 461 regarding requests for acceleration.  We remind you
that the company and its management are responsible for the accuracy and adequacy of their
disclosures, notwithstanding any review, comments, action or absence of action by the staff.
            Please contact Madeleine Mateo at 202-551-3465 with any questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:       Blake Baron

CORRESP
1
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FOXO
Technologies Inc.

February 13, 2023

VIA EDGAR

U.S. Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C. 20549

RE:  FOXO Technologies Inc.

Amendment No. 2 to Registration Statement on
Form S-1

Filed February 10, 2023

File No. 333-268980

Acceleration Request

Requested Date: Tuesday, February 14, 2023

Requested Time: 3:00 p.m. Eastern Time

Ladies and Gentlemen:

In accordance with Rule 461
under the Securities Act of 1933, as amended, the undersigned registrant (the “Registrant”) hereby requests
that the Securities and Exchange Commission (the “Commission”) take appropriate action to cause the above-referenced
Registration Statement on Form S-1 (File No. 333-268980) (the “Registration Statement”) to become effective
on Tuesday, February 14, 2023, at 3:00 p.m. Eastern Time, or as soon thereafter as possible, or at such later time as the Registrant or
its outside counsel, Mitchell Silberberg & Knupp LLP, may orally request via telephone call to the staff.

Once the Registration Statement
has been declared effective, please orally confirm that event with our outside counsel by calling Blake Baron at (917) 546-7709.

    Very truly yours,

    FOXO Technologies Inc.

    By:
    /s/ Tyler Danielson

    Tyler Danielson

    Interim Chief Executive Officer

FOXO Technologies Inc. – 729 N. Washington
Ave., Suite 600, Minneapolis, MN 55401– Tel: 612.562.9447

CORRESP
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    Mitchell Silberberg &
Knupp llp

    A Law Partnership Including
    Professional

 Corporations

VIA EDGAR

February 10, 2023

U.S. Securities & Exchange Commission

Division of Corporation Finance

Office of Finance

100 F Street, NE

Washington, D.C. 20549

    Attn:
    David Gessert

    David Lin

    Division of Corporation Finance

    Office of Finance

    Re:
    FOXO Technologies Inc.

    Registration Statement on Form S-1

    Filed December 23, 2022

    File No. 333-268980

Ladies and Gentlemen:

On behalf of our client, FOXO
Technologies Inc., a Delaware corporation (the “Company” or “FOXO”), and pursuant to the applicable
provisions of the Securities Act of 1933, as amended, and the rules promulgated thereunder, we are submitting (i) this letter to the Securities
and Exchange Commission (the “Commission”) via EDGAR in response to the comment letter to Mr. Robert Potashnick, the
Company’s Chief Financial Officer, from the staff of the Commission (the “Staff”), dated February 9, 2023 (the
“FOXO Comment Letter”), pertaining to the Company’s above-referenced Registration Statement on Form S-1 (the
Registration Statement”) and (ii) a complete copy of Amendment No. 2 (“Amendment No. 2”) to the Registration
Statement.

Amendment No. 2 reflects certain
revisions to the Registration Statement in response to the FOXO Comment Letter and other updated information.

The numbered paragraphs in
bold below set forth the Staff’s comments together with the Company’s responses. Disclosure changes made in response to the
Staff’s comments have been made in Amendment No. 2, which is being filed with the Commission contemporaneously with the submission
of this letter. Unless otherwise indicated, capitalized terms used herein have the meanings assigned to them in the Amendment No. 2.

    437 Madison Ave., 25th Floor, New York, New York 10022-7001

Phone:  (212) 509-3900  Fax:  (212) 509-7239  Website: www.msk.com

Page 2

Amendment No. 2 to the Registration Statement on Form S-1

General

1. We
note your revised disclosure in response to comments 1 and 3. Please revise to disclose on the cover page and pages ii, 6 and 111 the
price that the permitted transferees of the Sponsor paid for the securities being registered for resale (i.e., the shares of Class A
Common Stock and the warrants to purchase shares of Class A Common Stock that they received from the Sponsor) or advise. Also please
disclose the potential profit the selling securityholders (including the permitted transferees of the Sponsor) could earn based on the
current trading price.

Response: In response
to the Staff’s comment, the Company has revised the disclosure on the prospectus cover page, and pages ii, 6 and 111 of Amendment
No. 2 to reflect that the Sponsor distributed these securities to its members, for no additional consideration in connection with
its dissolution and distribution of all of its assets and has included the potential profit the selling securityholders could earn based
on the current trading price.

Cover Page

2. We
note your revised disclosure in response to comment 5 on pages 9 and 49, in the Risk Factor and MD&A sections, respectively, and
we reissue the comment. To the extent that all or most of the shares being registered for resale were purchased by the selling securityholders
for prices considerably below the current market price of your Class A Common Stock, please highlight on your prospectus cover page the
significant negative impact sales of shares on this registration statement could have on the public trading price of your Class A Common
Stock.

Response: In response
to the Staff’s comment, the Company has updated the disclosure on the prospectus cover page of Amendment No. 2.

Page 3

Prospectus Summary

Recent Developments, page 4

3. We
note your revised disclosure in response to comment 2. Please expand your disclosure on page 4 to describe the business activities or
segments that you will retain assuming the sale of FOXO Life Insurance is completed..

Response: In response
to the Staff’s comment, the Company has expanded the disclosure on page 4 of Amendment No. 2.

Risk Factors

Sales of a substantial number of our securities in the public market
by the Selling Securityholders….., page 9

4. We
note your added risk factor disclosure on page 9 in response to comment 6. Please expand this risk factor to disclose the percentage
that the securities being registered for resale currently represent of the total number of your shares outstanding. Additionally, disclose
the purchase price of the securities being registered paid by the permitted transferees of the Sponsor, or advise. Noting your disclosure
in the third paragraph of this risk factor, please identify the section and page number in the prospectus where differences in the purchase
prices paid by the selling securityholders (including the permitted transferees of the Sponsor) and public securityholders is described.

Response: In response
to the Staff’s comment, the Company has expanded the risk factor disclosure on page 9 of Amendment No. 2.

There is no guarantee that the exercise price
of our Warrants will ever be less than the trading price of our Common Stock….., page 13

5. We
note your added risk factor disclosure on page 13 in response to comment 8 that you may lower the exercise price of the Public Warrants
and the Private Warrants in accordance with Section 9.8 of the Warrant Agreement. Please revise the prospectus cover page to also disclose
that you may lower the exercise price of the Public Warrants and the Private Warrants and provide similar disclosure in the prospectus
summary, MD&A and use of proceeds sections. Also please provide appropriate cross-references to your disclosure in the section headed
"Description of Securities of the Company - Warrants" to accompany this added disclosure.

Response: In response
to the Staff’s comment, the Company has revised the disclosure in the prospectus summary, MD&A and use of proceeds sections
of Amendment No. 2.

Description of Securities

Warrants, page 104

6. Please revise this section of your filing to disclose whether
you have any current plans or intentions to lower the exercise price of the Public Warrants and the Private Warrants in accordance with
Section 9.8 of the Warrant Agreement, as referenced on page 13. Also please revise to disclose the material terms of this provision,
including, without limitation:

    ●
    The circumstances under which you would lower the exercise price and the purpose thereof;

    ●
    How and when the exercise price of each warrant may be adjusted; and

    ●
    Whether you can lower the exercise price for some but not all warrants.

Response: In response
to the Staff’s comment, the Company has revised the disclosure on page 104 of Amendment No. 2.

Page 4

We thank the Staff for its review of the foregoing
and Amendment No. 1. If you have further comments, please do not hesitate to contact me at bjb@msk.com or by telephone at (917) 546-7709.

    Sincerely,

    /s/ Blake Baron

    Name:  Blake Baron

cc: Robert Potashnick, FOXO Technologies Inc.

Nimish Patel, Mitchell Silberberg & Knupp LLP

United States securities and exchange commission logo
February 9, 2023
Tyler Danielson
Interim Chief Executive Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, MN 55401
Re:FOXO Technologies Inc.
Amendment No. 1 to Registration Statement on Form S-1
Filed January 30, 2023
File No. 333-268980
Dear Tyler Danielson:
            We have reviewed your amended registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.  Unless we note
otherwise, our references to prior comments are to comments in our January 19, 2023 letter.
Amendment No. 1 to Registration Statement on Form S-1
General
1.We note your revised disclosure in response to comments 1 and 3.  Please revise to
disclose on the cover page and pages ii, 6 and 111 the price that the permitted transferees
of the Sponsor paid for the securities being registered for resale (i.e., the shares of Class A
Common Stock and the warrants to purchase shares of Class A Common Stock that they
received from the Sponsor) or advise.  Also please disclose the potential profit the selling
securityholders (including the permitted transferees of the Sponsor) could earn based on
the current trading price.

 FirstName LastNameTyler Danielson
 Comapany NameFOXO Technologies Inc.
 February 9, 2023 Page 2
 FirstName LastName
Tyler Danielson
FOXO Technologies Inc.
February 9, 2023
Page 2
Cover Page
2.We note your revised disclosure in response to comment 5 on pages 9 and 49, in the Risk
Factor and MD&A sections, respectively, and we reissue the comment.  To the extent that
all or most of the shares being registered for resale were purchased by the selling
securityholders for prices considerably below the current market price of your Class A
Common Stock, please highlight on your prospectus cover page the significant negative
impact sales of shares on this registration statement could have on the public trading price
of your Class A Common Stock.
Prospectus Summary
Recent Developments, page 4
3.We note your revised disclosure in response to comment 2.  Please expand your disclosure
on page 4 to describe the business activities or segments that you will retain assuming the
sale of FOXO Life Insurance is completed.
Risk Factors
Sales of a substantial number of our securities in the public market by the Selling
Securityholders..., page 9
4.We note your added risk factor disclosure on page 9 in response to comment 6.  Please
expand this risk factor to disclose the percentage that the securities being registered for
resale currently represent of the total number of your shares outstanding.  Additionally,
disclose the purchase price of the securities being registered paid by the permitted
transferees of the Sponsor, or advise.  Noting your disclosure in the third paragraph of this
risk factor, please identify the section and page number in the prospectus where
differences in the purchase prices paid by the selling securityholders (including
the permitted transferees of the Sponsor) and public securityholders is described.
There is no guarantee that the exercise price of our Warrants will ever be less than the trading
price of our Common Stock..., page 13
5.We note your added risk factor disclosure on page 13 in response to comment 8 that you
may lower the exercise price of the Public Warrants and the Private Warrants in
accordance with Section 9.8 of the Warrant Agreement.  Please revise the prospectus
cover page to also disclose that you may lower the exercise price of the Public Warrants
and the Private Warrants and provide similar disclosure in the prospectus summary,
MD&A and use of proceeds sections.  Also please provide appropriate cross-references to
your disclosure in the section headed "Description of Securities of the Company -
Warrants" to accompany this added disclosure.

 FirstName LastNameTyler Danielson
 Comapany NameFOXO Technologies Inc.
 February 9, 2023 Page 3
 FirstName LastName
Tyler Danielson
FOXO Technologies Inc.
February 9, 2023
Page 3
Description of Securities of the Company
Warrants, page 104
6.Please revise this section of your filing to disclose whether you have any current plans or
intentions to lower the exercise price of the Public Warrants and the Private Warrants in
accordance with Section 9.8 of the Warrant Agreement, as referenced on page 13.  Also
please revise to disclose the material terms of this provision, including, without limitation:
•the circumstances under which you would lower the exercise price and the purpose
thereof;
•how and when the exercise price of each warrant may be adjusted; and
•whether you can lower the exercise price for some but not all warrants.
            Please contact David Gessert at (202) 551-2326 or David Lin at (202) 551-3552 with any
questions.
Sincerely,
Division of Corporation Finance
Office of Finance

CORRESP
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    Mitchell Silberberg &
    Knupp llp

    A Law Partnership Including Professional Corporations

VIA EDGAR

January 27, 2023

U.S. Securities & Exchange Commission

Division of Corporation Finance

Office of Finance

100 F Street, NE

Washington, D.C. 20549

    Attn:
    David Gessert

    David Lin

    Division of Corporation Finance

    Office of Finance

    Re:
    FOXO Technologies Inc.

    Registration Statement on Form S-1

    Filed December 23, 2022

    File No. 333-268980

Ladies and Gentlemen:

On behalf of our client, FOXO
Technologies Inc., a Delaware corporation (the “Company” or “FOXO”), and pursuant to the applicable
provisions of the Securities Act of 1933, as amended, and the rules promulgated thereunder, we are submitting (i) this letter to the Securities
and Exchange Commission (the “Commission”) via EDGAR in response to the comment letter to Mr. Robert Potashnick, the
Company’s Chief Financial Officer, from the staff of the Commission (the “Staff”), dated January 19, 2023 (the
“FOXO Comment Letter”), pertaining to the Company’s above-referenced Registration Statement on Form S-1 (the
Registration Statement”) and (ii) a complete copy of Amendment No. 1 (“Amendment No. 1”) to the Registration
Statement.

Amendment No. 1 reflects certain
revisions to the Registration Statement in response to the FOXO Comment Letter and other updated information.

The numbered paragraphs in
bold below set forth the Staff’s comments together with the Company’s responses. Disclosure changes made in response to the
Staff’s comments have been made in Amendment No. 1, which is being filed with the Commission contemporaneously with the submission
of this letter. Unless otherwise indicated, capitalized terms used herein have the meanings assigned to them in the Amendment No. 1.

    437 Madison Ave., 25th Floor, New York, New York 10022-7001

Phone:  (212) 509-3900  Fax:  (212) 509-7239  Website: www.msk.com

Page 2

Registration Statement on Form S-1 General

 1. Revise your prospectus to disclose the price that each selling
securityholder paid for the securities being registered for resale. Highlight any differences in the current trading price, the prices
that the Sponsor, private placement investors and other selling securityholders acquired their shares and warrants, and the price that
the public securityholders acquired their shares and warrants. Disclose that while the Sponsor, private placement investors and other
selling securityholders may experience a positive rate of return based on the current trading price, the public securityholders may not
experience a similar rate of return on the securities they purchased due to differences in the purchase prices and the current trading
price. Please also disclose the potential profit the selling securityholders will earn based on the current trading price. Lastly, please
include appropriate risk factor disclosure.

Response: In response
to the Staff’s comment, the Company has revised the disclosure on the prospectus cover page, and pages ii, 6 and 111 of Amendment
No. 1.

 2. Please revise to update your disclosures throughout the filing to address areas that appear to need updating
in light of developments since the consummation of your Business Combination. Non-exclusive examples of areas where disclosure should
be updated are as follows:

 ● Revise throughout to disclose your planned sale of FOXO Life to Security National Life Insurance Company,
as disclosed in your Form 8-K filed January 12, 2023, and discuss its impact upon your planned business activities;

Response:
In response to the Staff’s comment, the Company has updated the disclosure on pages 4, 38 and 48 of Amendment No. 1.

 ● Revise the Prospectus Summary to disclose the reasons the ELOC and Forward Purchase Agreements with the
Cantor Investor and Meteora, respectively, were terminated; and

Response:
In response to the Staff’s comment, the Company has updated the disclosure on pages 5, 38 and 39 of Amendment No. 1.

 ● Revise the Prospectus Summary to disclose the reasons why Jon Sabes and Steve Sabes were terminated as
the company’s Chief Executive Officer and Chairman and Chief Operating Officer, respectively. In this regard, we note that your
registration statement filed in connection with your Business Combination included risk factor disclosure that your future success depends
in large part on the continued participation in the business of Jon Sabes, FOXO’s founder and Chief Executive Officer of the combined
company. Please update your disclosure to address the risks related to Jon Sabes’ departure.

Response:
In response to the Staff’s comment, the Company has updated the disclosure on pages 5, 10 and 39 of Amendment No. 1.

Page 3

Cover Page

 3. For each of the Class A common shares and warrants being registered for resale, disclose the price that
the selling securityholders paid for such shares and warrants or the securities overlying such shares and warrants.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on the prospectus cover page, and pages ii, 9 and 111 of Amendment No. 1.

 4. Disclose the exercise price(s) of the warrants compared to the market price of the underlying security.
If the warrants are out the money, please disclose the likelihood that warrant holders will not exercise their warrants. Provide similar
disclosure in the prospectus summary, risk factors, MD&A and use of proceeds section and disclose that cash proceeds associated with
the exercises of the warrants are dependent on the stock price. As applicable, describe the impact on your liquidity and update the discussion
on the ability of your company to fund your operations on a prospective basis with your current cash on hand.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on the prospectus cover page, and pages 6, 9, 33 and 49 of Amendment No. 1.

 5. We note the significant number of redemptions of your Class A Common Stock in connection with your Business
Combination and that the shares being registered for resale will constitute a considerable percentage of your public float. To the extent
that all or most of the shares being registered for resale were purchased by the selling securityholders for prices considerably below
the current market price of your Class A Common Stock, please also highlight the significant negative impact sales of shares on this registration
statement could have on the public trading price of your Class A Common Stock.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on pages 9 and 49 of Amendment No. 1.

Risk Factors, page 8

 6. Include an additional risk factor highlighting the negative pressure potential sales of shares pursuant
to this registration statement could have on the public trading price of your Class A Common Stock. To illustrate this risk, disclose
the purchase price of the securities being registered for resale and the percentage that these shares currently represent of the total
number of shares outstanding. Also disclose, if true, that even though the current trading price is significantly below the SPAC IPO price,
certain private investors may have an incentive to sell because they may still profit on sales because of the lower price that they purchased
their shares than the public investors.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on page 9 of Amendment No. 1.

Page 4

Management’s Discussion and Analysis of Financial
Condition and Results of Operations, page 33

 7. We note that the projected revenues for 2022 were $2 million, as set forth in the unaudited prospective
financial information FOXO’s management provided to Delwinds in connection with the evaluation of the Business Combination. We also
note that your actual revenues for the Nine Months Ended September 30, 2022 were approximately $93 thousand. It appears that you will
miss your 2022 revenue projection. Please update your disclosure in Liquidity and Capital Resources, and elsewhere, to provide updated
information about the company’s financial position and further risks to the business operations and liquidity in light of these
circumstances.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on page 49 of Amendment No. 1.

Overview, page 33

 8. In light of the significant number of redemptions and the unlikelihood that the company will receive significant
proceeds from exercises of the warrants because of the disparity between the exercise price of the warrants and the current trading price
of your Class A Common Stock, expand your discussion of capital resources to address any changes in the company’s liquidity position
since the Business Combination. If the company is likely to have to seek additional capital, discuss the effect of this offering on the
company’s ability to raise additional capital.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on pages 9, 13 and 49 of Amendment No. 1.

 9. Please expand your discussion here to reflect the fact that this offering involves the potential sale of a substantial portion of
shares for resale and discuss how such sales could impact the market price of your Class A Common Stock.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on pages 9, 49, and 113 of Amendment No. 1.

 10. We note that in connection with the termination of your Forward Purchase Agreement with Meteora you repurchased
the remaining shares subject to the agreement that Meteora had not already sold in the open market and were not part of the maturity consideration.
Please revise to disclose the number of shares you repurchased and the per share and aggregate consideration you paid. Additionally, discuss
the impact of the repurchases on the cash you have available for other purposes and to execute your business strategy. Provide cross references
to this discussion elsewhere in the prospectus where this agreement is referenced.

Response: In response to the Staff’s
comment, the Company has revised the disclosure on pages 5 and 39 of Amendment No. 1.

Page 5

Executive Compensation, page 79

 11. We note that subsequent to the filing of Form S-1, the company’s fiscal year ended. Accordingly,
your next amendment should include updated executive compensation information for your most recently completed fiscal year pursuant to
Item 402 of Regulation S-K. For guidance, refer to Question 117.05 of the Compliance and Disclosure Interpretations for Regulation S-K.

Response: In response to the Staff’s
comment and pursuant to Item 402 of Regulation S-K, the Company has updated the executive compensation information in Amendment No. 1.

***

We thank the Staff for its review of the foregoing
and Amendment No. 1. If you have further comments, please do not hesitate to contact me at bjb@msk.com or by telephone at (917) 546-7709.

    Sincerely,

    /s/ Blake Baron

    Name:  Blake Baron

cc: Robert Potashnick, FOXO Technologies Inc.

Nimish Patel, Mitchell Silberberg & Knupp LLP

United States securities and exchange commission logo
January 19, 2023
Robert Potashnick
Chief Financial Officer
FOXO Technologies Inc.
729 N. Washington Ave., Suite 600
Minneapolis, MN 55401
Re:FOXO Technologies Inc.
Registration Statement on Form S-1
Filed December 23, 2022
File No. 333-268980
Dear Robert Potashnick:
            We have limited our review of your registration statement to those issues we have
addressed in our comments.  In some of our comments, we may ask you to provide us with
information so we may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.
Registration Statement on Form S-1
General
1.Revise your prospectus to disclose the price that each selling securityholder paid for the
securities being registered for resale.  Highlight any differences in the current trading
price, the prices that the Sponsor, private placement investors and other selling
securityholders acquired their shares and warrants, and the price that the public
securityholders acquired their shares and warrants.  Disclose that while the Sponsor,
private placement investors and other selling securityholders may experience a positive
rate of return based on the current trading price, the public securityholders may not
experience a similar rate of return on the securities they purchased due to differences in
the purchase prices and the current trading price.  Please also disclose the potential profit
the selling securityholders will earn based on the current trading price.  Lastly, please

 FirstName LastNameRobert Potashnick
 Comapany NameFOXO Technologies Inc.
 January 19, 2023 Page 2
 FirstName LastNameRobert Potashnick
FOXO Technologies Inc.
January 19, 2023
Page 2
include appropriate risk factor disclosure.
2.Please revise to update your disclosures throughout the filing to address areas that appear
to need updating in light of developments since the consummation of your Business
Combination.  Non-exclusive examples of areas where disclosure should be updated are as
follows:
•Revise throughout to disclose your planned sale of FOXO Life to Security National
Life Insurance Company, as disclosed in your Form 8-K filed January 12, 2023, and
discuss its impact upon your planned business activities;
•Revise the Prospectus Summary to disclose the reasons the ELOC and Forward
Purchase Agreements with the Cantor Investor and Meteora, respectively, were
terminated; and
•Revise the Prospectus Summary to disclose the reasons why Jon Sabes and Steve
Sabes were terminated as the company’s Chief Executive Officer and Chairman and
Chief Operating Officer, respectively.  In this regard, we note that your registration
statement filed in connection with your Business Combination included risk factor
disclosure that your future success depends in large part on the continued
participation in the business of Jon Sabes, FOXO’s founder and Chief Executive
Officer of the combined company.  Please update your disclosure to address the risks
related to Jon Sabes's departure.
Cover Page
3.For each of the Class A common shares and warrants being registered for resale, disclose
the price that the selling securityholders paid for such shares and warrants or the securities
overlying such shares and warrants.
4.Disclose the exercise price(s) of the warrants compared to the market price of the
underlying security.  If the warrants are out the money, please disclose the likelihood that
warrant holders will not exercise their warrants.  Provide similar disclosure in the
prospectus summary, risk factors, MD&A and use of proceeds section and disclose that
cash proceeds associated with the exercises of the warrants are dependent on the stock
price.  As applicable, describe the impact on your liquidity and update the discussion on
the ability of your company to fund your operations on a prospective basis with your
current cash on hand.
5.We note the significant number of redemptions of your Class A Common Stock in
connection with your Business Combination and that the shares being registered for resale
will constitute a considerable percentage of your public float.  To the extent that all or
most of the shares being registered for resale were purchased by the selling
securityholders for prices considerably below the current market price of your Class A
Common Stock, please also highlight the significant negative impact sales of shares on
this registration statement could have on the public trading price of your Class A Common
Stock.

 FirstName LastNameRobert Potashnick
 Comapany NameFOXO Technologies Inc.
 January 19, 2023 Page 3
 FirstName LastNameRobert Potashnick
FOXO Technologies Inc.
January 19, 2023
Page 3
Risk Factors, page 8
6.Include an additional risk factor highlighting the negative pressure potential sales of
shares pursuant to this registration statement could have on the public trading price of
your Class A Common Stock.  To illustrate this risk, disclose the purchase price of the
securities being registered for resale and the percentage that these shares currently
represent of the total number of shares outstanding.  Also disclose, if true, that even
though the current trading price is significantly below the SPAC IPO price, certain private
investors may have an incentive to sell because they may still profit on sales because of
the lower price that they purchased their shares than the public investors.
Management's Discussion and Analysis of Financial Condition and Results of Operations, page
33
7.We note that the projected revenues for 2022 were $2 million, as set forth in the unaudited
prospective financial information FOXO’s management provided to Delwinds in
connection with the evaluation of the Business Combination.  We also note that your
actual revenues for the Nine Months Ended September 30, 2022 were approximately $93
thousand.  It appears that you will miss your 2022 revenue projection.  Please update your
disclosure in Liquidity and Capital Resources, and elsewhere, to provide updated
information about the company’s financial position and further risks to the business
operations and liquidity in light of these circumstances.
Overview, page 33
8.In light of the significant number of redemptions and the unlikelihood that the company
will receive significant proceeds from exercises of the warrants because of the disparity
between the exercise price of the warrants and the current trading price of your Class A
Common Stock, expand your discussion of capital resources to address any changes in the
company’s liquidity position since the Business Combination.  If the company is likely to
have to seek additional capital, discuss the effect of this offering on the company’s ability
to raise additional capital.
9.Please expand your discussion here to reflect the fact that this offering involves the
potential sale of a substantial portion of shares for resale and discuss how such sales could
impact the market price of your Class A Common Stock.
10.We note that in connection with the termination of your Forward Purchase Agreement
with Meteora you repurchased the remaining shares subject to the agreement that Meteora
had not already sold in the open market and were not part of the maturity consideration.
Please revise to disclose the number of shares you repurchased and the per share and
aggregate consideration you paid.  Additionally, discuss the impact of the repurchases on
the cash you have available for other purposes and to execute your business strategy.
Provide cross references to this discussion elsewhere in the prospectus where this
agreement is referenced.

 FirstName LastNameRobert Potashnick
 Comapany NameFOXO Technologies Inc.
 January 19, 2023 Page 4
 FirstName LastName
Robert Potashnick
FOXO Technologies Inc.
January 19, 2023
Page 4
Executive Compensation, page 79
11.We note that subsequent to the filing of Form S-1, the company's fiscal year
ended.  Accordingly, your next amendment should include updated executive
compensation information for your most recently completed fiscal year pursuant to Item
402 of Regulation S-K.  For guidance, refer to Question 117.05 of the Compliance and
Disclosure Interpretations for Regulation S-K.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration.  Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.
            Please contact David Gessert at (202) 551-2326 or David Lin at (202) 551-3552 with any
questions.
Sincerely,
Division of Corporation Finance
Office of Finance

CORRESP
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filename1.htm

Delwinds Insurance Acquisition Corp.

One City Centre

1021 Main Street, Suite 1960

Houston, Texas 77002

August 25, 2022

VIA EDGAR

Division of Corporation Finance

Office of Finance

100 F Street N.E.

Washington, D.C. 20549

    Re:
    Delwinds Insurance Acquisition Corp.

    Amendment No. 5 to Registration Statement on Form S-4

    Filed August 25, 2022

    File No. 333-264216

Ladies and Gentleman:

Pursuant to Rule 461 under
the Securities Act of 1933, as amended, Delwinds Insurance Acquisition Corp. hereby requests acceleration of effectiveness of the above
referenced Registration Statement so that it will become effective at 4:00 p.m. ET on Friday, August 26, 2022, or as soon as thereafter
practicable.

    Very truly yours,

    /s/
Andrew Poole

    Andrew Poole

    Chief Executive Officer

    cc:

    Ellenoff Grossman & Schole LLP

CORRESP
1
filename1.htm

Delwinds Insurance Acquisition Corp.

One City Centre

1021 Main Street, Suite 1960

Houston, Texas 77002

VIA EDGAR

August 24, 2022

U.S. Securities & Exchange Commission

Division of Corporation Finance

Office of Finance

100 F Street, NE

Washington, D.C. 20549

Attn: John Stickel

Re: Delwinds Insurance Acquisition Corp.

Amendment No. 3 to Registration Statement on Form S-4

Filed August 12, 2022

File No. 333-264216

Dear Mr. Stickel:

Delwinds Insurance Acquisition
Corp. (the “Company,” “we,” “our” or “us”) hereby transmits
our response to the comment letter received from the staff (the “Staff,” “you” or “your”)
of the U.S. Securities and Exchange Commission (the “Commission”) on August 23, 2022 regarding Amendment No. 3 to Registration
Statement on Form S-4 (the “Registration Statement”) filed with the Commission on August 12, 2022. For your convenience,
we have repeated below your comments in bold, and have followed each comment with our response.

Amended Form S-4 filed August 12, 2022

General

1. Refer to your response to comment 9. We note your
disclosure at page 150 that the resignations “may be” an indication that RBCCM or DB do not want to be associated with the
disclosure in the joint proxy statement / consent solicitation / prospectus or underlying business analysis related to the
transaction. Please revise at pages 57, 150, and throughout, to remove “may be” from your disclosure to highlight for
investors that RBCCM’s and Deutsche Bank’s withdrawals indicate that they do not want to be associated with the disclosure or
underlying business analysis related to the transaction.

In response to the Staff’s comment, we have
revised the disclosure on pages 23, 57, and 150 of the Registration Statement.

Unaudited Pro Forma Condensed Combined Financial Information,
page 101

2. We note disclosure on page F-80 that you
entered into a consulting agreement in the second quarter of 2022. With reference to Rule 11-01(a)(8), please tell us your consideration
of presenting the pro forma impact of the agreement in your Article 11 pro forma information. Address the impact this transaction will
have on the pro forma combined financial statements, including the impact on the pro forma earnings per share and statement of operations,
and the related accounting implications. If material, this issuance should be presented separately within your pro forma financial information.

In response to the Staff’s comment, we have revised the disclosure
regarding the impact of the consulting agreement on pro forma earnings per share and the statements of operations on pages 54, 105-106,
109-110 and 112. The revised disclosure separately presents and shows the consummation of the agreement as if it had occurred at the
beginning of the fiscal year presented for the pro forma condensed combined statements of operations and the Company notes that the agreement
is already reflected in the historical balance sheet. Additionally, the accounting implications discussed on page F-80 are also included
in the revised disclosure.

***

We thank you for your review of the foregoing
and the amended Registration Statement. If you have further comments, please feel free to contact to our counsel, Meredith Laitner, Esq.,
at mlaitner@egsllp.com or by telephone at (212) 370-1300.

    Sincerely,

    /s/ Andrew Poole

    Andrew Poole

    Chief Executive Officer

    cc:
    Meredith Laitner, Esq.

    Ellenoff Grossman & Schole LLP

United States securities and exchange commission logo
August 23, 2022
Andrew Poole
Chief Executive Officer
Delwinds Insurance Acquisition Corp.
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
Re:Delwinds Insurance Acquisition Corp.
Amendment No. 3 to Registration Statement on Form S-4
Filed August 12, 2022
File No. 333-264216
Dear Mr. Poole:
            We have reviewed your amended registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.  Unless we note
otherwise, our references to prior comments are to comments in our August 1, 2022 letter.
Amended Form S-4 filed August 12, 2022
General
1.Refer to your response to comment 9.  We note your disclosure at page 150 that the
resignations "may be" an indication that RBCCM or DB do not want to be associated with
the disclosure in the joint proxy statement / consent solicitation / prospectus or underlying
business analysis related to the transaction.  Please revise at pages 57, 150, and
throughout, to remove "may be" from your disclosure to highlight for investors that
RBCCM's and Deutsche Bank’s withdrawals indicate that they do not want to be
associated with the disclosure or underlying business analysis related to the transaction.

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 August 23, 2022 Page 2
 FirstName LastName
Andrew Poole
Delwinds Insurance Acquisition Corp.
August 23, 2022
Page 2
Unaudited Pro Forma Condensed Combined Financial Information, page 101
2.We note disclosure on page F-80 that you entered into a consulting agreement in the
second quarter of 2022.  With reference to Rule 11-01(a)(8), please tell us your
consideration of presenting the pro forma impact of the agreement in your Article 11 pro
forma information.  Address the impact this transaction will have on the pro forma
combined financial statements, including the impact on the pro forma earnings per share
and statement of operations, and the related accounting implications.  If material, this
issuance should be presented separately within your pro forma financial information.
            You may contact Michael Henderson at 202-551-3364 or Robert Klein at 202-551-3847
if you have questions regarding comments on the financial statements and related
matters.  Please contact John Stickel at 202-551-3324 or Susan Block at 202-551-3210 with any
other questions.
Sincerely,
Division of Corporation Finance
Office of Finance
cc:       Meredith Laitner

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Delwinds Insurance Acquisition Corp.

One City Centre

1021 Main Street, Suite 1960

Houston, Texas 77002

VIA EDGAR

August 12, 2022

U.S. Securities & Exchange Commission

Division of Corporation Finance

Office of Finance

100 F Street, NE

Washington, D.C. 20549

Attn: John Stickel

Re: Delwinds Insurance Acquisition Corp.

Amendment No. 2 to Registration Statement on Form S-4

Filed July 8, 2022

File No. 333-264216

Dear Mr. Stickel:

Delwinds Insurance Acquisition
Corp. (the “Company,” “we,” “our” or “us”) hereby transmits
our response to the comment letter received from the staff (the “Staff,” “you” or “your”)
of the U.S. Securities and Exchange Commission (the “Commission”) on August 1, 2022 regarding Amendment No. 2 to Registration
Statement on Form S-4 (the “Registration Statement”) filed with the Commission on July 8, 2022. For your convenience,
we have repeated below your comments in bold, and have followed each comment with our response.

Amendment No. 2 to the Form S-4 filed July 8, 2022

Support Subscription Agreements, page 34

1. Please revise to explain why the Threshold Amount was reduced
as a result of the RBCCM Termination.

In response to the Staff’s comment,
we have revised the disclosure on page 34 of the Registration Statement.

General

2. With a view toward disclosure, please tell
us whether your sponsor is, is controlled by, or has substantial ties with a non-U.S. person. Please also tell us whether anyone or any
entity associated with or otherwise involved in the transaction, is, is controlled by, or has substantial ties with a non-U.S. person.
If so, also include risk factor disclosure that addresses how this fact could impact your ability to complete your initial business combination.
For instance, discuss the risk to investors that you may not be able to complete an initial business combination with a U.S. target company
should the transaction be subject to review by a U.S. government entity, such as the Committee on Foreign Investment in the United States
(CFIUS), or ultimately prohibited. Further, disclose that the time necessary for government review of the transaction or a decision to
prohibit the transaction could prevent you from completing an initial business combination and require you to liquidate. Disclose the
consequences of liquidation to investors, such as the losses of the investment opportunity in a target company, any price appreciation
in the combined company, and the warrants, which would expire worthless.

Delwinds’ sponsor, DIAC Sponsor LLC (the “Sponsor”), is a Delaware limited liability company, which is not controlled
by, and does not have substantial ties to, any non-U.S. person. Andrew J. Poole, Delwinds’ Chief Executive Officer and Chairman,
a U.S. citizen, is the sole managing member of the Sponsor. Neither Mr. Poole nor, to the best of Delwinds’ knowledge, any other
member of the Sponsor is controlled by, or has any substantial ties to, any non-U.S. person. To the best of FOXO’s knowledge, there
are no officers, directors or stockholders involved in the transaction that is, is controlled by, or has substantial ties with a non-U.S.
person. Notwithstanding the above, we have revised the disclosure to add a risk factor on page 63 of the Registration Statement to address
risks related to non-U.S. person involvement in the transaction.

3. We note that Deutsche Bank Securities Inc.
(“Deutsche Bank”) has resigned and is ending its involvement with this registration statement. Please disclose the resignation
in the registration statement, including the reason for the resignation, and explain the Implications for the transaction and investors.

On June 16, 2022, Deutsche Bank
resigned from its role as financial advisor to FOXO. Deutsche Bank informed FOXO management of its decision to resign from its role
as financial advisor and file the 11(b)(1) letter with the SEC. No reason for the resignation was stated in the resignation letter.
As Deutsche Bank’s role in the Business Combination was substantially complete, FOXO did not consider Deutsch Bank’s
resignation to be material to the Business Combination and Deutsche Bank’s resignation did not impact the FOXO Board’s
analysis of, or its continued support of the Business Combination.

FOXO does not believe there will be
any adverse implications to investors as it pertains to the resignation of Deutsch Bank. However, as FOXO will not be required to pay
the fees due to Deutsche Bank upon the Closing, FOXO’s aggregate transaction expenses will be reduced.

In addition, in response to the Staff’s
comment, we have revised the disclosure on the cover of the Registration, as well as pages 23, 49, 57, 148-151 of the Registration Statement.

4. Please tell us whether RBC Capital Markets,
LLC (“RBCCM”) or Deutsche Bank were involved in the preparation of any disclosure that is included in the registration statement,
or material underlying disclosure in the registration statement, including but not limited to the disclosure regarding the summary of
the financial analyses prepared by FOXO Technologies Inc.’s (“FOXO”) management and reviewed by the board of directors
of Delwinds Insurance Acquisition Corp. (“Delwinds”) or the projected financial information of FOXO. If so, clarify their
involvement, whether they have retracted any work product associated with the transaction, and the risk of such withdrawal and reliance
on their expertise. If RBCCM or Deutsche Bank were involved in preparing disclosure, please also include a risk factor describing their
role in connection with the preparation of the registration statement and the valuation of FOXO and that they disclaim any liability in
connection with such disclosure included in the registration statement. If applicable, please also clarify that RBCCM or Deutsche Bank
claim no role in the SPAC’s business combination transaction and have affirmatively disclaimed any responsibility for any of the
disclosure in this registration statement. Please also disclose the rationale for continuing to rely on information disclaimed by the
professional organization associated with or responsible for such information, if applicable. Please note that comments in this letter
apply to RBCCM’s and Deutsche Banks’s and their respective subsidiaries and affiliates in any capacity.

Neither RBCCM nor Deutsche Bank was
responsible for the preparation of any disclosure that is included in the Registration Statement, or any analysis underlying such disclosure.
Together with all other members of the transaction working group, RBCCM and Deutsche Bank received drafts of the Registration Statement
prepared by the parties and provided limited comments in the ordinary course.

Disclosure to this effect has been added
on pages 23, 49, 57 and 148-151 of the Registration Statement.

    2

5. Please disclose whether Deutsche Bank assisted
in the preparation or review of any materials reviewed by the Delwinds board of directors or management as part of their services to FOXO
and whether Deutsche Bank has withdrawn their association with those materials and notified Delwinds of such disassociation. Similarly
disclosure whether RBCCM assisted in the preparation or review of any materials reviewed by Delwinds board of directors or management
as part of its services and whether RBCCM has withdrawn their association with those materials and notified Delwinds of such disassociation.
For context, include that there are similar circumstances in which a financial institution is named and that a firm’s resignation
indicates they are not willing to have the liability associated with such work in that transaction.

Delwinds did not rely on RBCCM, in its
role as Delwinds’ financial advisor or capital markets advisor, in the preparation and analysis of the materials provided to the
Delwinds Special Committee and Delwinds Board for use as a component of their overall evaluation of FOXO. The Delwinds Special Committee
(nor the Delwinds Board) did not receive or rely upon any financial or valuation analyses conducted or prepared by RBCCM in making its
determination that the Business Combination is fair to and in the best interests of Delwinds and its stockholders.

Deutsche Bank did not assist in the
preparation or review of any materials reviewed by the Delwinds board of directors or management as part of their services to FOXO.

Disclosure to this effect has been
added on pages 148-151 of the Registration Statement.

6. Please provide us with any correspondence
between RBCCM and Delwinds, and Deutsche Bank and FOXO, relating to the respective resignations.

In response to the Staff’s comment,
the Company has provided under separate cover (i) the termination letter from Deutsche Bank to FOXO and (ii) the termination letter from
RBCCM to Delwinds .

7. Please provide us with the engagement letters
between RBCCM and Delwinds, and Deutsche Bank and FOXO. Please disclose any ongoing obligations of the companies pursuant to the engagement
letter that will survive the termination of the engagement, such as indemnification provisions, rights of first refusal, and lockups,
and discuss the impacts of those obligations on the companies in the registration statement.

In response to the Staff’s comment, the Company has provided
under separate cover (i) the engagement letter between Deutsche Bank and FOXO and (ii) the engagement letter between RBCCM and Delwinds
and we have revised the disclosure on pages 148-151 of the Registration Statement.

    3

8. Please provide us with a letter from RBCCM
stating whether it agrees with the statements made in your prospectus related to their resignation and, if not, stating the respects
in which they do not agree. Please revise your disclosure accordingly to reflect that you have discussed the disclosure with RBCCM and
it either agrees or does not agree with the conclusions and the risks associated with such outcome. If RBCCM does not respond, please
revise your disclosure to indicate you have asked and not received a response and disclose the risks to investors. Please provide similar
disclosure regarding Deutsche Bank’s resignation as FOXO’s advisor, as applicable. Additionally, please indicate that RBCCM
and Deutsche Bank withdrew from their role as financial advisors and forfeited their fees, if applicable, and that the firms refused
to discuss the reasons for its resignation and forfeiture of fees, if applicable, with management. Clarify whether RBCCM and Deutsche
Bank performed substantially all the work to earn their fees.

The Company respectfully informs the
Staff that Delwinds requested a letter from RBCCM stating whether it agrees with the statements made in the Registration Statement related
to their resignation and, if not, stating the respects in which they do not agree, and has not received a response. As requested by the
Staff, we have revised the disclosure on page 148-151 of the Registration Statement disclosing that RBCCM has neither expressed agreement
or disagreement with the risks or conclusions stated in the Registration Statement that are associated with RBCCM’s role. Accordingly,
no inference should be drawn that RBCCM agrees with the disclosure regarding its resignation or any other portion of the Registration
Statement. Further, in response to the Staff’s comment, Delwinds undertakes that it will not speculate in the Registration Statement
or make any public statements about the reasons why RBCCM withdrew from its role as financial advisor and forfeited its fee after doing
substantially all of the work to earn its fee.

The Company respectfully informs the
Staff that similarly, FOXO requested a letter from Deutsche Bank stating whether it agrees with the statements made in the Registration
Statement related to their resignation and, if not, stating the respects in which they do not agree, and has not received a response.
As requested by the Staff, we have revised the disclosure on page 148-151 of the Registration Statement disclosing that FOXO received
a response letter from Deutsche Bank stating it agreed with the disclosures in the joint proxy statement/consent solicitation statement/prospectus
pertaining to its resignation.

9. Please revise your disclosure to highlight
for investors that RBCCM and Deutsche Bank’s withdrawals indicate that they do not want to be associated with the disclosure or
underlying business analysis related to the transaction. In addition, revise your disclosure to caution investors that they should not
place any reliance on the fact that RBCCM and Deutsche Bank had been previously involved with the transaction.

The Company respectfully advises the
Staff that, while RBCCM has disclaimed responsibility for the disclosure included in the Registration Statement, RBCCM and has not informed
the Company or FOXO that it does not wish to be associated with the disclosure or underlying business analysis related to the Business
Combination. As requested by the Staff, we have revised the disclosure on the cover page of the Registration Statement, as well as on
page 57-58 and 148-151 of the Registration Statement disclosing that RBCCM has disclaimed any responsibility for the disclosures made
in the Registration Statement and cautioning investors not to rely on the fact that RBCCM was involved with any aspect of the Business
Combination.

Additionally, Deutsche Bank disclaimed any responsibility for any portion
of the registration statement, or any future amendments thereto, filed by Delwinds or any of their respective affiliates in connection
with this transaction. Furthermore, investors should not place any reliance on the fact that Deutsche Bank was previously involved with
the transaction. As requested by the Staff, we have revised the disclosure on the cover page of the Registration Statement, as well as
on pages 57-58 and 148-151.

    4

10. Please discuss the potential impact on
the transaction related to the resignation of RBCCM and Deutsche Bank. We note that RBCCM was an underwriter for the IPO of the SPAC and
both RBCCM and Deutsche Bank are advising or have advised on the business combination transactions. If RBCCM or Deutsche Bank would have
played a role in the closing, please revise to identify the party who will be filling their respective roles.

The Company respectfully advises the
Staff that because RBCCM and Deutsche Bank’s respective financial advisory services on the Business Combination were substantially
complete, the Company believes that the resignation of RBCCM and Deutsche Bank will not delay FOXO’s entry into the public market
and the closing of the Business Combination, and Delwinds and FOXO, respectively, do not expect to hire additional financial advisors
in connection with the Business Combination.

In addition, in response to the Staff’s
comment, we have revised the disclosure on the cover of the Registration, as well as pages 23, 49, 57-58, 148-151 of the Registration
Statement.

11. Please disclose any fees paid or due to
RBCCM or Deutsche Bank in connection with their role as a financial advisor. If any of these fees will be forfeited by their resignation,
please revise to disclose this information.

Delwinds paid RBCCM an aggregate of $2,012,500 upon consummation of
its IPO as fees for acting as IPO underwriter. Additionally, RBCCM waived its deferred fee in connection with its role as an IPO underwriter,
in an aggregate amount of $4,021,875. Delwinds did not pay any fees to RBCCM in connection with their role as Delwinds’ financial
advisor. Pursuant to the resignation letter sent from RBCCM to Delwinds on June 1, 2022, RBCCM waived its entitlement to any fees and
the payment of any compensation that had accrued or may in the future accrue or become due under the RBCCM Engagement Letter.

FOXO did not pay any fees to Deutsche
Bank in connection with their role as FOXO’s financial advisor. Pursuant to the resignation letter sent from Deutsche Bank to FOXO
on June 16, 20

United States securities and exchange commission logo
August 1, 2022
Andrew Poole
Chief Executive Officer
Delwinds Insurance Acquisition Corp.
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
Re:Delwinds Insurance Acquisition Corp.
Amendment No. 2 to Registration Statement on Form S-4
Filed July 8, 2022
File No. 333-264216
Dear Mr. Poole:
            We have reviewed your amended registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.  Unless we note
otherwise, our references to prior comments are to comments in our May 27, 2022 letter.
Amendment No. 2 to the Form S-4 filed July 8, 2022
Support Subscription Agreements, page 34
1.Please revise to explain why the Threshold Amount was reduced as a result of the
RBCCM Termination.
General
2.With a view toward disclosure, please tell us whether your sponsor is, is controlled by, or
has substantial ties with a non-U.S. person.  Please also tell us whether anyone or any
entity associated with or otherwise involved in the transaction, is, is controlled by, or has
substantial ties with a non-U.S. person.  If so, also include risk factor disclosure that

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 August 1, 2022 Page 2
 FirstName LastNameAndrew Poole
Delwinds Insurance Acquisition Corp.
August 1, 2022
Page 2
addresses how this fact could impact your ability to complete your initial business
combination.  For instance, discuss the risk to investors that you may not be able to
complete an initial business combination with a U.S. target company should the
transaction be subject to review by a U.S. government entity, such as the Committee on
Foreign Investment in the United States (CFIUS), or ultimately prohibited.  Further,
disclose that the time necessary for government review of the transaction or a decision to
prohibit the transaction could prevent you from completing an initial business
combination and require you to liquidate.  Disclose the consequences of liquidation to
investors, such as the losses of the investment opportunity in a target company, any price
appreciation in the combined company, and the warrants, which would expire worthless.
3.We note that Deutsche Bank Securities Inc. (“Deutsche Bank”) has resigned and is ending
its involvement with this registration statement.  Please disclose the resignation in the
registration statement, including the reason for the resignation, and explain the
implications for the transaction and investors.
4.Please tell us whether RBC Capital Markets, LLC (“RBCCM”) or Deutsche Bank were
involved in the preparation of any disclosure that is included in the registration statement,
or material underlying disclosure in the registration statement, including but not limited to
the disclosure regarding the summary of the financial analyses prepared by FOXO
Technologies Inc.’s (“FOXO”) management and reviewed by the board of directors of
Delwinds Insurance Acquisition Corp. (“Delwinds”) or the projected financial information
of FOXO.  If so, clarify their involvement, whether they have retracted any work product
associated with the transaction, and the risk of such withdrawal and reliance on their
expertise.  If RBCCM or Deutsche Bank were involved in preparing disclosure, please
also include a risk factor describing their role in connection with the preparation of the
registration statement and the valuation of FOXO and that they disclaim any liability in
connection with such disclosure included in the registration statement.  If applicable,
please also clarify that RBCCM or Deutsche Bank claim no role in the SPAC’s business
combination transaction and have affirmatively disclaimed any responsibility for any of
the disclosure in this registration statement.  , Please also disclose the rationale for
continuing to rely on information disclaimed by the professional organization associated
with or responsible for such information, if applicable. Please note that comments in this
letter apply to RBCCM's and Deutsche Banks's and their respective subsidiaries and
affliates in any capacity.
5.Please disclose whether Deutsche Bank assisted in the preparation or review of any
materials reviewed by the Delwinds board of directors or management as part of their
services to FOXO and whether Deutsche Bank has withdrawn their association with those
materials and notified Delwinds of such disassociation.  Similarly disclosure whether
RBCCM assited in the preparation or review of any materials reviewed by Delwinds
board of directors or managment as part of its services and whether RBCCM has
withdrawn their association with those materials and notified Delwinds of such
disassociation. For context, include that there are similar circumstances in which a

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 August 1, 2022 Page 3
 FirstName LastNameAndrew Poole
Delwinds Insurance Acquisition Corp.
August 1, 2022
Page 3
financial institution is named and that a firm’s resignation indicates they are not willing to
have the liability associated with such work in that transaction.
6.Please provide us with any correspondence between RBCCM and Delwinds, and
Deutsche Bank and FOXO, relating to the respective resignations.
7.Please provide us with the engagement letters between RBCCM and Delwinds, and
Deutsche Bank and FOXO.  Please disclose any ongoing obligations of the companies
pursuant to the engagement letter that will survive the termination of the engagement,
such as indemnification provisions, rights of first refusal, and lockups, and discuss the
impacts of those obligations on the companies in the registration statement.
8.Please provide us with a letter from RBCCM stating whether it agrees with the statements
made in your prospectus related to their resignation and, if not, stating the respects in
which they do not agree.  Please revise your disclosure accordingly to reflect that you
have discussed the disclosure with RBCCM and it either agrees or does not agree with the
conclusions and the risks associated with such outcome.  If RBCCM does not respond,
please revise your disclosure to indicate you have asked and not received a response and
disclose the risks to investors.  Please provide similar disclosure regarding Deutsche
Bank's resignation as FOXO's advisor, as applicable.  Additionally, please indicate that
RBCCM and Deutsche Bank withdrew from their role as financial advisors and forfeited
their fees, if applicable, and that the firms refused to discuss the reasons for its resignation
and forfeiture of fees, if applicable, with management.  Clarify whether RBCCM and
Deutsche Bank performed substantially all the work to earn their fees.
9.Please revise your disclosure to highlight for investors that RBCCM and Deutsche Bank’s
withdrawals indicate that they do not want to be associated with the disclosure or
underlying business analysis related to the transaction.  In addition, revise your disclosure
to caution investors that they should not place any reliance on the fact that RBCCM and
Deutsche Bank had been previously involved with the transaction.
10.Please discuss the potential impact on the transaction related to the resignation of RBCCM
and Deutsche Bank.  We note that RBCCM was an underwriter for the IPO of the SPAC
and both RBCCM and Deutsche Bank are advising or have advised on the business
combination transactions.  If RBCCM or Deutsche Bank would have played a role in the
closing, please revise to identify the party who will be filling their respective roles.
11.Please disclose any fees paid or due to RBCCM or Deutsche Bank in connection with
their role as a financial advisor.  If any of these fees will be forfeited by their resignation,
please revise to disclose this information.
12.We understand that RBCCM, an underwriter in your SPAC IPO, intends to waive the
deferred underwriting commissions that would otherwise be due to it upon the closing of
the business combination.  Please disclose how this waiver was obtained, why the waiver
was agreed to, and clarify the SPAC’s current relationship with RBCCM.  Revise your pro
forma financial information and relevant disclosure referring to the payment of deferred

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 August 1, 2022 Page 4
 FirstName LastName
Andrew Poole
Delwinds Insurance Acquisition Corp.
August 1, 2022
Page 4
underwriting commissions.
13.Please describe what relationship existed between RBCCM and Delwinds after the close
of the IPO, including any financial or merger-related advisory services conducted by
RBCCM. For example, clarify whether RBCCM had any role in the identification or
evaluation of business combination targets.
14.Please tell us whether you are aware of any disagreements with RBCCM or Deutsche
Bank regarding the disclosure in your registration statement.  Further, please add risk
factor disclosure that clarifies that RBCCM was to be compensated, in part, on a deferred
basis for its underwriting services in connection with the SPAC IPO and such services
have already been rendered, yet RBCCM is waiving such fees and disclaiming
responsibility for the Form S-4 registration statement.  Clarify the unusual nature of such a
fee waiver and the impact of it on the evaluation of the business combination.
15.Disclose whether RBCCM provided you with any reasons for the fee waiver.  If there was
no dialogue and you did not seek out the reasons why RBCCM was waiving deferred fees,
despite already completing their services, please indicate so in your registration statement.
Further, revise the risk factor disclosure to explicitly clarify that RBCCM has performed
all their obligations to obtain the fee and therefore is gratuitously waiving the right to be
compensation.
            You may contact Michael Henderson at 202-551-3364 or Robert Klein at 202-551-3847
if you have questions regarding comments on the financial statements and related
matters.  Please contact John Stickel at 202-551-3324 or Susan Block at 202-3210 with any other
questions.
Sincerely,
Division of Corporation Finance
Office of Finance

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Delwinds Insurance Acquisition Corp.

One City Centre

1021 Main Street, Suite 1960

Houston, Texas 77002

VIA EDGAR

July 8, 2022

U.S. Securities & Exchange Commission

Division of Corporation Finance

Office of Finance

100 F Street, NE

Washington, D.C. 20549

Attn: John Stickel

    Re:
    Delwinds Insurance Acquisition Corp.

Amendment No. 1 to Registration Statement
on Form S-4

Filed May 13, 2022

File No. 333-264216

Dear Mr. Stickel:

Delwinds Insurance Acquisition Corp. (the “Company,”
“we,” “our” or “us”) hereby transmits our response to the comment letter received
from the staff (the “Staff,” “you” or “your”) of the U.S. Securities and Exchange
Commission (the “Commission”) on May 27, 2022 regarding Amendment No. 1 to Registration Statement on Form S-4 (the
“Registration Statement”) filed with the Commission on May 13, 2022. For your convenience, we have repeated below your
comments in bold, and have followed each comment with our response.

Amendment No. 1 to the Form S-4 filed May 13, 2022

Proprietary Insurance Products, page 212

 1. We note your response to prior comment 12 and reissue
in part. Consistent with your response and the disclosure added on page 83, please clarify here that the purchase of Memorial Insurance
Company of America primarily involved the purchase of a license to conduct insurance business and not a material amount of existing insurance
business, or advise.

In response to the Staff’s comment, we have revised
the disclosure on page 214 of the Registration Statement.

Commercialization of Saliva-Based Epigenic Biomarkers, page 217

 2. We note your response to prior comment 14 and reissue
in part. We note your disclosure that your research and development efforts are in various stages of design and completion and that you
may be in a position to begin using epigenetic biomarkers in a commercial underwriting context in 2023. We also note your disclosure
that the amount of research and development you will conduct will depend upon your capital following the Transactions, and the amount
of research and development you require to commercially sell our epigenetic biomarker underwriting technology will depend upon the results
you obtain from such research. Please expand to briefly explain the material anticipated steps involved and the projected material costs
involved to get the technology to the point where you believe it will be ready for commercialized use. To the extent the steps and costs
may vary based on the capital available following the Transactions or the results of initial research, provide a range of reasonable
possibilities that are anticipated. In addition, consistent with your disclosure on page 219, clarify throughout the prospectus where
appropriate that you do not expect to use epigenetic underwriting technology in the life insurance products you sell initially, and while
you hope to support commercialization of your saliva-based underwriting technology by 2023, there is no guarantee.

In response to the Staff’s comment, we have revised
the disclosure regarding our research and development efforts on pages 218 – 221. We have also revised our disclosure throughout
the prospectus to clarify that we do not expect to use epigenetic underwriting technology in the life insurance products we sell initially,
and while we hope to support commercialization of your saliva-based underwriting technology by 2023, there is no guarantee.

***

We thank you for your review of the foregoing and the amended Registration
Statement. If you have further comments, please feel free to contact to our counsel, Meredith Laitner, Esq., at mlatner@egsllp.com or
by telephone at (212) 370-1300.

    Sincerely,

    /s/ Andrew Poole

    Andrew Poole

    Chief Executive Officer

    cc:
    Meredith Laitner, Esq.

    Ellenoff Grossman & Schole LLP

June 16, 2022
Securities and Exchange Commission
I 00 F Street. N. E.
Washington. D.C. 20549
Re: Registra!ion Statemenf on Form S-4 (Registration No. 333-264216)
To whom it may concern:· · ·
Reference is made to the above-referenced registration statement. as amended (the
··Registration Statement'"). ·of Delwihds Insurance Acquisition Corp. (the --issuer'") under the
Securities Act of I 933, as amended (the ··Securities Act'"). with respect to a proposed business
combination transactii:m , involving the Issuer. a special purpose acquisition company. and FOXO
Technologies Inc., a Delaware corporation (the --Transaction··). The Registration Statement has
not yet been declared effective as of the date and time of this letter.
This letter is to advise you that. effective as of June 16. 2022. our firm has resigned from.
or ceased or refused to act in. every capacity and relationship in which we were described in the
Registration Statement as acting or agreeing to act with respect to the Transaction.
Therefore. we hereby advise you and the Issuer. pursuant to Section I l(b)( I) of the
Securities Act, that none of our firm. any person who controls it (within the meaning of either
Section 15 of the Securities Act or Section 20 of the Securities Exchange Act of 1934. as amended)
or any of its affiliates (within the meaning of Rule 405 under the Securities Act) wil I be responsible
for any part of the Registration Statement. This notice is not intended to constitute an
acknowledgment or admission that we have been or are an underwriter (v,,ithin the meaning of
Section 2(a)( I 1) of the Securities Act or the rules and regulations promulgated thereunder) with
respect to the Transaction.
[Remainder of this page intentional~v le.fi blank]
-1888-1846-2756 '3
Confidential

Sincerely.
Deutsche Bank Securities Inc.
cc: John Stickel. Securities and Exchange Commission
Susan Block. Securities and Exchange Commission
Michael Henderson. Securities and Exchange Commission
Robert Klein. Securities and Exchange Commission
Jon Sa bes. Chief Executive Officer of FOXO Technologies. Inc.
2
Confidential -1888-1846-2756 , 3

United States securities and exchange commission logo
May 27, 2022
Andrew Poole
Chief Executive Officer
Delwinds Insurance Acquisition Corp.
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
Re:Delwinds Insurance Acquisition Corp.
Amendment No. 1 to Registration Statement on Form S-4
Filed May 13, 2022
File No. 333-264216
Dear Mr. Poole:
            We have reviewed your amended registration statement and have the following
comments.  In some of our comments, we may ask you to provide us with information so we
may better understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.  Unless we note
otherwise, our references to prior comments are to comments in our May 5, 2022 letter.
Amendment No. 1 to the Form S-4 filed May 13, 2022
Proprietary Insurance Products, page 212
1.We note your response to prior comment 12 and reissue in part.  Consistent with your
response and the disclosure added on page 83, please clarify here that the purchase of
Memorial Insurance Company of America primarily involved the purchase of a license to
conduct insurance business and not a material amount of existing insurance business, or
advise.
Commercialization of Saliva-Based Epigenic Biomarkers, page 217
2.We note your response to prior comment 14 and reissue in part.  We note your disclosure

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 May 27, 2022 Page 2
 FirstName LastName
Andrew Poole
Delwinds Insurance Acquisition Corp.
May 27, 2022
Page 2
that your research and development efforts are in various stages of design and completion
and that you may be in a position to begin using epigenetic biomarkers in a commercial
underwriting context in 2023.  We also note your disclosure that the amount of research
and development you will conduct will depend upon your capital following the
Transactions, and the amount of research and development you require to commercially
sell our epigenetic biomarker underwriting technology will depend upon the results
you obtain from such research.  Please expand to briefly explain the material anticipated
steps involved and the projected material costs involved to get the technology to the point
where you believe it will be ready for commercialized use.  To the extent the steps and
costs may vary based on the capital available following the Transactions or the results of
initial research, provide a range of reasonable possibilities that are anticipated.  In
addition, consistent with your disclosure on page 219, clarify throughout the prospectus
where appropriate that you do not expect to use epigenetic underwriting technology in the
life insurance products you sell initially, and while you hope to support commercialization
of your saliva-based underwriting technology by 2023, there is no guarantee.
            You may contact Michael Henderson at 202-551-3364 or Robert Klein at 202-551-3847
if you have questions regarding comments on the financial statements and related
matters.  Please contact John Stickel at 202-551-3324 or Susan Block at 202-551-3210 with any
other questions.
Sincerely,
Division of Corporation Finance
Office of Finance

CORRESP
1
filename1.htm

Delwinds
Insurance Acquisition Corp.

One
City Centre

1021
Main Street, Suite 1960

Houston,
Texas 77002

VIA
EDGAR

May
13, 2022

U.S.
Securities & Exchange Commission

Division of Corporation Finance

Office
of Finance

100
F Street, NE

Washington,
D.C. 20549

Attn: John Stickel

 Re: Delwinds
Insurance Acquisition Corp.

Registration
Statement on Form S-4

Filed
April 8, 2022

Registration No. 333-264216

Dear Mr. Stickel:

Delwinds Insurance Acquisition Corp. (the “Company,”
“we,” “our” or “us”) hereby transmits our response to the comment letter received
from the staff (the “Staff,” “you” or “your”) of the U.S. Securities and Exchange
Commission (the “Commission”) on May 5, 2022 regarding the above Registration Statement on Form S-4 (the “Registration
Statement”) filed with the Commission on April 8, 2022. In response to the Staff’s comments, the Company has revised the Registration
Statement and is submitting via Edgar an amended Registration Statement with this response letter. For your convenience, we have repeated
below your comments in bold, and have followed each comment with our response.

Form
S-4 filed April 8, 2022

Summary
of the Joint Proxy Statement/Consent Solicitation Statement/Prospectus, page 31

 1. Please provide a graphic depiction of the organization of Delwinds
and FOXO prior to the business combination. Please also include a post-combination organizational chart that includes the percentage of
voting power that Delwinds’ current public shareholders will have, taking into account the voting power of any Class V shares.

In response to the Staff’s comment, we have included
the requested disclosure on pages 35-36 of the amended Registration Statement.

Parties
to the Business Combination

FOXO
Technologies, page 31

 2. Please
                                            also disclose here that FOXO is a development stage company and has not been profitable since
                                            its inception. Please also include FOXO’s revenues and net losses for the most recent audited
                                            period.

In response to the Staff’s comment, we have revised
the disclosure on page 32 of the amended Registration Statement.

The
Proposed Charter will designate a state or federal court located within the State of Delaware, page 59

 3. We note that your risk factor discusses the additional costs you could
incur associated with resolving such action in other jurisdictions. Please also describe the risk that the choice of forum provision may
increase the costs for shareholders to bring a claim.

 In response to the Staff’s comment, we have revised
the disclosure on page 63 of the amended Registration Statement.

Risk
Factors

Certain
Delwinds warrants are accounted for as a liability, page 65

 4. We
                                            note your reference to the SEC Staff Statement and as a result of the Staff Statement you
                                            reevaluated the accounting treatment of the Delwinds warrants. This statement appears to
                                            qualify the accounting treatment and indicate your accounting treatment of the Delwinds warrants
                                            is based on the Staff Statement. Please tell us how this disclosure is appropriate in light
                                            of the audit report that states that the financial statements are the responsibility of management
                                            and in which your auditor opines that the financial statements present fairly, in all material
                                            respects, your financial position and the results of your operations and cash flows in conformity
                                            with accounting principles generally accepted in the United States of America.

In response to the Staff’s comment, we have revised
the disclosure on page 68 of the amended Registration Statement.

    2

The
Combined Company may redeem unexpired Public Warrants prior to their exercise at a time that is disadvantageous for warrant holders,
page 67

 5. Please
                                            clearly explain the steps, if any, the company will take to notify all shareholders, including
                                            beneficial owners, regarding when the warrants become eligible for redemption. Also expand
                                            your disclosure on page 237 to describe the method of such notification. In addition, highlight
                                            here or in another risk factor the material risks to public warrant holders arising from
                                            differences between private and public warrants.

In response to the Staff’s comment, we have revised
the disclosure on pages 25, 70,71 and 242 of the amended Registration Statement.

FOXO’s underwriting technology and consumer engagement
services may now or in the future be subject to laws and regulations, page 78

 6. Please
                                            clarify if there is a risk regarding the legality of using saliva-based or other biomarker
                                            technology that you intend to use for underwriting insurance, at either the state or federal
                                            level.

In response to the Staff’s comment, we have revised
the disclosure on page 82 of the amended Registration Statement.

The
NTA Proposal, page 120

 7. We
                                            note the NTA Proposal, if approved, would remove the condition that the net tangible assets
                                            be at least $5,0 00,001 prior to the consummation of the merger. We also note that this proposal
                                            is not conditioned upon any other proposal and appears this change to the charter would be
                                            in place even if this merger is not consummated. Please expand to include a complete explanation
                                            of how shareholders will or could be affected by the change. Please also include risk factor
                                            disclosure regarding this potential change even if the merger is not consummated, as applicable.
                                            Please provide an analysis of why a redemption right is not required in connection with this
                                            change, given the change appears that it may occur, even if the merger is not consummated,
                                            or advise.

In response to the Staff’s comment, we have revised
the disclosure throughout the amended Registration Statement to condition the NTA Proposal on the approval of the Business Combination
Proposal and to state that the NTA Amendments would not be implemented if the Business Combination Proposal is not approved. Therefore,
the risks associated with such changes if the Business Combination is not consummated are not applicable and an independent redemption
right for the NTA Proposal is not required under Delwinds’ amended and restated certificate of incorporation.

    3

The
Business Combination Proposal

Interests
of Delwinds’ Initial Stockholders, Directors and Officers in the Business Combination, page 132

 8. Please
                                            quantify the aggregate dollar amount and describe the nature of what the sponsor and its
                                            affiliates have at risk that depends on the completion of a business combination. Include
                                            the current value of securities held, loans extended, fees due, and out-of-pocket expenses
                                            for which the sponsor and its affiliates are awaiting reimbursement. Provide similar disclosure
                                            for the company’s officers and directors, if material. Provide similar disclosure, as applicable,
                                            under “Questions and Answers About the Delwinds Special Meeting,” at page 15.

In response to the Staff’s comment, we have revised
the disclosure on pages 18-20 and 118 of the amended Registration Statement to (i) add the aggregate amount at risk to the sponsors and
its affiliates and (ii) make more prominent the disclosure with respect to the sponsor’s and its affiliates’ interests that
depend on the completion of a business combination.

Background
of the Business Combination, page 135

 9. Please disclose the negotiation of any arrangements whereby any shareholder
agreed to waive its redemption rights.

In response to the Staff’s comment, we have revised
the disclosure on pages 138 and 143 of the amended Registration Statement.

Certain
Projected Financial Information, page 150

      10. We
                                            note your attempt to limit reliance on the disclosed financial projections. Although you
                                            may place the disclosed information in appropriate context, by disclosing underlying assumptions
                                            and discussing the purposes for which the information was prepared, because this information
                                            constitutes public disclosure, you may not limit reliance in this way. Please revise to remove
                                            broad limitations on reliance.

In response to the Staff’s comment, we have revised
the disclosure on pages 153 and154 of the amended Registration Statement.

    4

Redemption
Rights for Public Stockholders upon Completion of our Initial Business

Combination,
page 187

 11. We
                                            note that certain shareholders agreed to waive their redemption rights. If applicable, please
                                            describe any consideration provided in exchange for this agreement.

In response to the Staff’s comment, we have revised
the disclosure on page 190 of the amended Registration Statement.

Insurance
Products Platform: FOXO Life, page 209

 12. Please
                                            clarify if FOXO’s purchase of Memorial Insurance Company of America involved the purchase
                                            of a material amount of existing insurance business, or if it primarily involved the purchase
                                            of a license to conduct insurance business. Also provide such clarity on pages 43 and 79
                                            when referencing its acquisition of a life insurance company.

In response to the Staff’s comment, FOXO’s purchase
of Memorial Insurance Company of America (“MICOA”) (now known as FOXO Life Insurance Company) primarily involved the
purchase of a license to conduct insurance business. In connection with this transaction, the seller (Security National Life Insurance
Company (“SNLIC”)) and MICOA entered into an Amended and Restated Reinsurance Agreement whereby the pre-acquisition
100% coinsurance of all of MICOA’s life insurance policies by SNLIC, with all administration also provided by SNLIC, were continued
indefinitely after the acquisition of MICOA.

In addition, we have revised the disclosure on pages 47 and
83 of the amended Registration Statement.

 13. Please
                                            provide support for the statement that in your experience legacy life insurance carriers
                                            operate on legacy technology, cannot rapidly prototype and iterate, and are challenged to
                                            effectively use technology to improve their products and realize cost efficiencies, or revise
                                            to state as your belief.

In response to the Staff’s comment, we have revised
the disclosure on page 212 of the amended Registration Statement.

Commercialization
of Saliva-Based Epigenic Biomarkers, page 214

    5

 14. We
                                            note your disclosure that you are still early in development of your epigenetic biomarker
                                            technology and currently have various research initiatives to further develop, improve and
                                            validate epigenetic biomarkers with accuracies for commercialized use.

Please
expand to briefly explain the material anticipated steps involved, timelines, and any material costs involved to get the technology to
the point where you believe it will be ready for commercialized use.

In response to the Staff’s comment, we have revised
the disclosure on pages 218 and219 of the amended Registration Statement.

Technology
Operations,

page
216

 15. We
                                            note that FOXO is developing an operational software platform with advanced architecture
                                            in lieu of using currently available industry software “plug and play” options.
                                            We further note that its ability to develop this technology innovation stack is supported
                                            by what it believes are best-in-class no-code software and cloud computing platforms. Please
                                            balance your disclosure about the anticipated benefits of developing a custom operating platform
                                            with a brief discussion of the potential risks involved, as well at the expected costs and
                                            timelines. Also, identify the best-in-class no-code software and cloud computing platforms
                                            with which you reference and intend to utilize.

In response to the Staff’s comment, we have revised
the disclosure on page 220 of the amended Registration Statement.

Management’s
Discussion and Analysis of Financial Condition and Results of Operations of FOXO Results of Operations

Research
and Development, page 225

 16. We
                                            note that the increase in the research and development expenses was primarily due to costs
                                            associated with sponsored research projects with Harvard University’s Brigham and Women’s
                                            Hospital, the U.S. Department of Health and Human Services, and The Children’s Hospital
                                            of Philadelphia. Please revise to expand your discussion to quantify the costs associated
                                            with each project during the periods presented, as well as greater clarity into the stage
                                            of the project and nature of the costs incurred.

In response to the Staff’s comment, we have revised
the disclosure on page 228 of the amended Registration Statement.

Beneficial
Ownership of Securities, page 256

 17. Please
                                            provide the natural person(s) who have voting and dispositive control over the shares owned
                                            by Shaolin Capital Management LLC, Saba Capital Management, L.P., Adage Capital Partners,
                                            L.P., and Cinctive Global Master Fund Ltd.

In response to the Staff’s comment, we have revised
the footnotes to the beneficial ownership table on page 262 of the amended Registration Statement. With respect to Shaolin Capital Management
LLC (“Shaolin”), no information as to a natural person having voting and dispositive control was furnished in the Schedule
13G filed by Shaolin with the Commission on February 10, 2022.

Board

United States securities and exchange commission logo
May 5, 2022
Andrew Poole
Chief Executive Officer
Delwinds Insurance Acquisition Corp.
One City Centre
1021 Main Street, Suite 1960
Houston, Texas 77002
Re:Delwinds Insurance Acquisition Corp.
Registration Statement on Form S-4
Filed April 8, 2022
File No. 333-264216
Dear Mr. Poole:
            We have reviewed your registration statement and have the following comments.  In
some of our comments, we may ask you to provide us with information so we may better
understand your disclosure.
            Please respond to this letter by amending your registration statement and providing the
requested information.  If you do not believe our comments apply to your facts and
circumstances or do not believe an amendment is appropriate, please tell us why in your
response.
            After reviewing any amendment to your registration statement and the information you
provide in response to these comments, we may have additional comments.
Form S-4 filed April 8, 2022
Summary of the Joint Proxy Statement/Consent Solicitation Statement/Prospectus, page 31
1.Please provide a graphic depiction of the organization of Delwinds and FOXO prior to the
business combination.  Please also include a post-combination organizational chart that
includes the percentage of voting power that Delwind's current public shareholders will
have, taking into account the voting power of any Class V shares.
Parties to the Business Combination
FOXO Technologies, page 31
2.Please also disclose here that FOXO is a development stage company and has not been
profitable since its inception.  Please also include FOXO's revenues and net losses for the

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 May 5, 2022 Page 2
 FirstName LastNameAndrew Poole
Delwinds Insurance Acquisition Corp.
May 5, 2022
Page 2
most recent audited period.
The Proposed Charter will designate a state or federal court located within the State of Delaware,
page 59
3.We note that your risk factor discusses the additional costs you could incur associated
with resolving such action in other jurisdictions.  Please also describe the risk that the
choice of forum provision may increase the costs for shareholders to bring a claim.
Risk Factors
Certain Delwinds warrants are accounted for as a liability, page 65
4.We note your reference to the SEC Staff Statement and as a result of the Staff Statement
you reevaluated the accounting treatment of the Delwinds warrants.  This statement
appears to qualify the accounting treatment and indicate your accounting treatment of the
Delwinds warrants is based on the Staff Statement.  Please tell us how this disclosure is
appropriate in light of the audit report that states that the financial statements are the
responsibility of management and in which your auditor opines that the financial
statements present fairly, in all material respects, your financial position and the results of
your operations and cash flows in conformity with accounting principles generally
accepted in the United States of America.
The Combined Company may redeem unexpired Public Warrants prior to their exercise at a time
that is disadvantageous for warrant holders, page 67
5.Please clearly explain the steps, if any, the company will take to notify all
shareholders, including beneficial owners, regarding when the warrants become eligible
for redemption.  Also expand your disclosure on page 237 to describe the method of such
notification.  In addition, highlight here or in another risk factor the material risks to
public warrant holders arising from differences between private and public warrants.
FOXO's underwriting technology and consumer engagement services may now or in the future
be subject to laws and regulations, page 78
6.Please clarify if there is a risk regarding the legality of using saliva-based or other
biomarker technology that you intend to use for underwriting insurance, at either the state
or federal level.
The NTA Proposal, page 120
7.We note the NTA Proposal, if approved, would remove the condition that the net tangible
assets be at least $5,000,001 prior to the consummation of the merger.  We also note that
this proposal is not conditioned upon any other proposal and appears this change to the
charter would be in place even if this merger is not consummated.  Please expand to
include a complete explanation of how shareholders will or could be affected by the
change.  Please also include risk factor disclosure regarding this potential change even if

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 May 5, 2022 Page 3
 FirstName LastNameAndrew Poole
Delwinds Insurance Acquisition Corp.
May 5, 2022
Page 3
the merger is not consummated, as applicable.  Please provide an analysis of why a
redemption right is not required in connection with this change, given the change appears
that it may occur, even if the merger is not consummated, or advise.
The Business Combination Proposal
Interests of Delwinds' Initial Stockholders, Directors and Officers in the Business Combination,
page 132
8.Please quantify the aggregate dollar amount and describe the nature of what the sponsor
and its affiliates have at risk that depends on the completion of a business combination.
Include the current value of securities held, loans extended, fees due, and out-of-pocket
expenses for which the sponsor and its affiliates are awaiting reimbursement.  Provide
similar disclosure for the company's officers and directors, if material.  Provide similar
disclosure, as applicable, under "Questions and Answers About the Delwinds Special
Meeting," at page 15.
Background of the Business Combination, page 135
9.Please disclose the negotiation of any arrangements whereby any shareholder agreed to
waive its redemption rights.
Certain Projected Financial Information, page 150
10.We note your attempt to limit reliance on the disclosed financial projections.  Although
you may place the disclosed information in appropriate context, by disclosing
underlying assumptions and discussing the purposes for which the information was
prepared, because this information constitutes public disclosure, you may not limit
reliance in this way.  Please revise to remove broad limitations on reliance.
Redemption Rights for Public Stockholders upon Completion of our Initial Business
Combination, page 187
11.We note that certain shareholders agreed to waive their redemption rights.  If applicable,
please describe any consideration provided in exchange for this agreement.
Insurance Products Platform: FOXO Life, page 209
12.Please clarify if FOXO'x purchase of Memorial Insurance Company of America involved
the purchase of a material amount of existing insurance business, or if it primarily
involved the purchase of a license to conduct insurance business.  Also provide such
clarity on pages 43 and 79 when referencing its acquisition of a life insurance company.
13.Please provide support for the statement that in your experience legacy life insurance
carriers operate on legacy technology, cannot rapidly prototype and iterate, and are
challenged to effectively use technology to improve their products and realize cost
efficiencies, or revise to state as your belief.

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 May 5, 2022 Page 4
 FirstName LastNameAndrew Poole
Delwinds Insurance Acquisition Corp.
May 5, 2022
Page 4
Commercialization of Saliva-Based Epigenic Biomarkers, page 214
14.We note your disclosure that you are still early in development of your epigenetic
biomarker technology and currently have various research initiatives to further develop,
improve and validate epigenetic biomarkers with accuracies for commercialized use.
Please expand to briefly explain the material anticipated steps involved, timelines, and any
material costs involved to get the technology to the point where you believe it will be
ready for commercialized use.
Technology Operations, page 216
15.We note that FOXO is developing an operational software platform with advanced
architecture in lieu of using currently available industry software “plug and play” options.
We further note that its ability to develop this technology innovation stack is supported by
what it believes are best-in-class no-code software and cloud computing platforms.  Please
balance your disclosure about the anticipated benefits of developing a custom operating
platform with a brief discussion of the potential risks involved, as well at the expected
costs and timelines.  Also, identify the best-in-class no-code software and cloud
computing platforms with which you reference and intend to utilize.
Management's Discussion and Analysis of Financial Condition and Results of Operations of
FOXO
Results of Operations
Research and Development, page 225
16.We note that the increase in the research and development expenses was primarily due to
costs associated with sponsored research projects with Harvard University’s Brigham and
Women’s Hospital, the U.S. Department of Health and Human Services, and The
Children’s Hospital of Philadelphia.  Please revise to expand your discussion to quantify
the costs associated with each project during the periods presented, as well as greater
clarity into the stage of the project and nature of the costs incurred.
Beneficial Ownership of Securities, page 256
17.Please provide the natural person(s) who have voting and dispositive control over the
shares owned by Shaolin Capital Management LLC, Saba Capital Management,
L.P., Adage Capital Partners, L.P., and Cinctive Global Master Fund Ltd.
Board Committees, page 263
18.We note your disclosure on page 72 that you may be exposed to security incidents related
to your platforms.  To the extent cybersecurity risks are material to your business, please
disclose here or in another appropriately captioned section the nature of the board’s role in
overseeing your cybersecurity risk management, the manner in which the board will
administer this oversight function and any effect this will have on the board’s leadership

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 May 5, 2022 Page 5
 FirstName LastName
Andrew Poole
Delwinds Insurance Acquisition Corp.
May 5, 2022
Page 5
structure.
Consolidated Statements of Stockholders Equity' (Deficit) and Members' Equity, page F-23
19.We note your presentation of adjustments for the Corporate Conversion during the year
ended December 31, 2020.  Please provide us with your accounting analysis explaining
the adjustments, including the adjustment to accumulated deficit of $(12,494), recognized
to give effective Corporate Conversion.
Notes to Consolidated Financial Statements
Note 3. Summary of Significant Accounting Policies
Revenue Recognition, page F-28
20.We note your disclosure that the Company earns royalties on epigenetic biomarkers global
sales and commissions on life insurance policies based on a percentage of premiums paid.
Please revise your disclosure to quantify or provide a range of the percentage amounts
generated for the royalties and commissions.
Exhibits and Financial Statement Schedules, page II-1
21.Please confirm that you will file the employment agreements referenced on pages 124 and
270 as exhibits once you enter into them with your officers.
General
22.Please include the preliminary proxy card with the next amendment.
            We remind you that the company and its management are responsible for the accuracy
and adequacy of their disclosures, notwithstanding any review, comments, action or absence of
action by the staff.
            Refer to Rules 460 and 461 regarding requests for acceleration.  Please allow adequate
time for us to review any amendment prior to the requested effective date of the registration
statement.
            You may contact Michael Henderson at 202-551-3364 or Robert Klein at 202-551-
3847 if you have questions regarding comments on the financial statements and related
matters.  Please contact John Stickel at 202-551-3324  or Susan Block at 202-551-3210 with any
other questions.
Sincerely,
Division of Corporation Finance
Office of Finance

CORRESP
1
filename1.htm

December 8, 2020

VIA EDGAR

United States Securities and Exchange Commission

Division of Corporation Finance

100 F Street, N.E.

Washington, D.C.  20549

Attention: Jonathan Burr

    Re:
    Delwinds Insurance Acquisition Corp.

    Registration Statement on Form S-1

    Filed September 11, 2020, as amended

    File No. 333-248753

Dear Mr. Burr:

Pursuant to Rule 461 of the General Rules and Regulations under
the Securities Act of 1933, as amended (the “Act”), the undersigned, for themselves and the several underwriters, hereby
join in the request of Delwinds Insurance Acquisition Corp. that the effective date of the above-referenced Registration Statement
be accelerated so as to permit it to become effective at 4:00 p.m. Washington D.C. time on December 10, 2020, or as soon thereafter
as practicable.

Pursuant to Rule 460 of the General Rules and Regulations under
the Act, the undersigned advise that approximately 500 copies of the Preliminary Prospectus dated December 1, 2020 are expected
to be distributed to prospective underwriters and dealers, institutional investors, retail investors and others.

The undersigned advise that they have complied and will continue
to comply with the requirements of Rule 15c2-8 under the Securities Exchange Act of 1934, as amended.

* * *

[Signature page follows]

Very truly yours,

RBC CAPITAL MARKETS, LLC

CANTOR FITZGERALD & CO.

as Representatives of the Several Underwriters

RBC CAPITAL MARKETS, LLC

By:	/s/
Michael Ventura

        Name:	Michael Ventura

        Title:	Managing Director, ECM

CANTOR FITZGERALD & CO.

By:	/s/
Bala Murty

       Name:	Bala Murty

       Title:	Chief Operating Officer

[Signature Page to Underwriters’ Acceleration
Request]

CORRESP
1
filename1.htm

Delwinds Insurance Acquisition Corp.

One City Centre

1021 Main Street, Suite 1960

Houston, TX 77002

December 8, 2020

VIA EDGAR

U.S. Securities and Exchange Commission

100 F Street, N.E.

Washington, D.C. 20549

Attention: Jonathan Burr

    Re:
    Delwinds Insurance Acquisition Corp.

    Registration Statement on Form S-1, as amended

    Filed September 11, 2020

    File No. 333- 248753

Dear Mr. Burr:

Pursuant to Rule 461 under the Securities Act
of 1933, as amended, Delwinds Insurance Acquisition Corp. hereby requests acceleration of effectiveness of the above referenced
Registration Statement so that it will become effective at 4:00 p.m. EST on December 10, 2020, or as soon as thereafter practicable.

    Very truly yours,

    /s/ Andrew J. Poole

    Andrew J. Poole

    Chief Executive Officer

    cc:

    Ellenoff Grossman & Schole LLP

    Skadden, Arps, Slate, Meagher & Flom LLP

CORRESP
1
filename1.htm

VIA
EDGAR

September
11, 2020

U.S.
Securities and Exchange Commission

100
F Street, N.E.

Washington,
D.C. 20549

Attention:
Jonathan Burr

 Re: Delwinds
Insurance Acquisition Corp.

Draft
Registration Statement on Form S-1

Submitted
June 9, 2020

CIK
0001812360

Dear
Mr. Burr:

Delwinds
Insurance Acquisition Corp. (the “Company,” “we,” “our” or “us”) hereby transmits
its response to the comment letter received from the staff (the “Staff”) of the Securities and Exchange Commission
(the “Commission”), dated July 2, 2020, regarding the Draft Registration Statement on Form S-1 submitted on June 9,
2020.

For
the Staff’s convenience, we have repeated below the Staff’s comments in bold, and have followed each comment with
the Company’s response.

Draft
Registration Statement on Form S-1 submitted June 9, 2020

Exclusive
Forum for Certain Lawsuits, page 127

 1. We
                                         note that your exclusive forum provision does not apply to actions arising under the
                                         Securities Act or Exchange Act. Please ensure that the exclusive forum provision in the
                                         governing documents states this clearly, or tell us how you will inform investors in
                                         future filings that the provision does not apply to any actions arising under the Securities
                                         Act or Exchange Act.

We
hereby confirm to the Staff that our Amended and Restated Certificate of Incorporation will state clearly that the exclusive forum
provision does not apply to actions arising under the Securities Act or the Exchange Act.

*    *    *

We
thank the Staff in advance for its consideration of the foregoing. Should you have any questions, please do not hesitate to contact
our legal counsel, Stuart Neuhauser Esq., of Ellenoff Grossman & Schole LLP, at (212) 370-1300.

    Very
    truly yours,

    Delwinds
    Insurance Acquisition Corp.

    By:
    /s/ Andrew Poole

    Name:
     Andrew Poole

    Title:
     Chief Executive Officer

cc:
Ellenoff Grossman & Schole LLP

United States securities and exchange commission logo
July 2, 2020
Andrew Poole
Chief Executive Officer
Delwinds Insurance Acquisition Corp.
c/o Ellenoff Grossman & Schole LLP
1345 Avenue of the Americas
New York, NY 10105
Re:Delwinds Insurance Acquisition Corp.
Draft Registration Statement on Form S-1
Submitted June 9, 2020
CIK 0001812360
Dear Mr. Poole:
            We have reviewed your draft registration statement and have the following comment.  In
our comment, we may ask you to provide us with information so we may better understand your
disclosure.
            Please respond to this letter by providing the requested information and either submitting
an amended draft registration statement or publicly filing your registration statement on
EDGAR.  If you do not believe our comment applies to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.
            After reviewing the information you provide in response to this comment and your
amended draft registration statement or filed registration statement, we may have additional
comments.
Draft Registration Statement on Form S-1 submitted June 9, 2020
Exclusive Forum for Certain Lawsuits, page 127
1.We note that your exclusive forum provision does not apply to actions arising under the
Securities Act or Exchange Act.  Please ensure that the exclusive forum provision in
the governing documents states this clearly, or tell us how you will inform investors in
future filings that the provision does not apply to any actions arising under the Securities
Act or Exchange Act.

 FirstName LastNameAndrew Poole
 Comapany NameDelwinds Insurance Acquisition Corp.
 July 2, 2020 Page 2
 FirstName LastName
Andrew Poole
Delwinds Insurance Acquisition Corp.
July 2, 2020
Page 2
            You may contact William Demarest at 202-551-3432 or Shannon Menjivar at 202-551-
3856 if you have questions regarding comments on the financial statements and related
matters.  Please contact Jonathan Burr at 202-551-5833 or Erin E. Martin at 202-551-3391 with
any other questions.
Sincerely,
Division of Corporation Finance
Office of Real Estate & Construction