SecProbe.io

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                                 (212) 701-3186

                                                                October 21, 2004

                          Re: Z-Tel Technologies, Inc.
                              Schedule TO-I
                              Originally filed September 30, 2004
                              File No. 005-57653

Dear Ms. Chalk:

     On behalf of Z-Tel Technologies, Inc., this letter is provided in
connection with Amendment No. 1 to Z-Tel's Schedule TO referenced above.
Amendment No. 1 contains changes in response to your letter dated October 18,
2004.

     Z-Tel is also filing today an amended preliminary proxy statement
containing changes conforming it to Amendment No. 1, where appropriate.

     The captions and numbered responses below correspond to the captions and
numbered paragraphs in your letter. Capitalized terms used in the responses
below have the meanings provided in Amendment No. 1.

General

     1. Comment: We note that the consummation of this offer is conditioned on
the receipt of shareholder approval for the offer and certain related
transactions. Consider explaining why you commenced this offer before obtaining
the required shareholder approval. Revise the offer materials to indicate the
approximate time frame for obtaining the approval of shareholders, and to
explain that this offer must be extended until you obtain such approval.

     Response: Disclosure has been added in Amendment No. 1 in response to this
comment explaining that because the Offer is required to be kept open for a
minimum of 20 business days, Z-Tel determined that it should attempt to
synchronize the Offer period and the notice period for the Special Meeting so
that they would run concurrently, with an overall view towards most
ex-

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peditiously and efficiently consummating the Exchange Offer and transactions
contemplated by the Special Meeting Matters. Amendment No. 1 also extends
expiration of the Offer to 5:00PM, Eastern Time, on Tuesday, November 23, 2004,
which is the close of business on the fifth business day following the presently
anticipated Special Meeting date of Tuesday, November 16, 2004. Please see the
cover page and page 6 of the Offer to Exchange contained in Amendment No. 1.

     2. Comment: It appears that the materials you filed on Schedule TO on
September 30, 2004 may be soliciting materials with respect to the proxy
solicitation presented in the proxy statement you filed on October 6, 2004.
Similarly, the proxy statement appears to may constitute written communications
made by the issuer relating to the issuer tender offer within the meaning of
Rule 13e-4(c). In the future, consider whether communications related to your
solicitation should also be filed as offer materials under cover of Schedule TO,
and vice versa.

     Response: Amendment No. 1 has been filed as soliciting material with
respect to the amended preliminary proxy statement and the amended preliminary
proxy statement has been filed as a written communication by the issuer relating
to the Exchange Offer, in each case via EDGAR transmission in response to this
comment.

     3. Comment: We note the disclosure that consummation of the exchange offer
is conditioned on the tender by the 1818 Fund of all preferred stock that it
owns, and that the representatives of the 1818 Fund have indicated that they
intend to tender their shares of preferred stock in the offer if "substantially
all" of the shares of the preferred stock held by others are tendered. Explain
mechanically how this will work. That is, how will the 1818 Fund gain access to
this information while the offer remains open? If you intend to share this
information with the 1818 Fund, will you also disclose it generally, and if so,
by what means?

     Response: Please note that two of Z-Tel's directors are affiliated with The
1818 Fund and in such capacities will have access to information provided to
Z-Tel concerning tenders of Preferred Stock. To facilitate disclosure of tenders
to all holders of Preferred Stock, Z-Tel has determined that it will disclose,
by means of a press release, the amounts of each series of Preferred Stock
tendered as of the close of business (1) on the second business day preceding
the Special Meeting date and (2) on the second business day prior to expiration
of the Offer. Z-Tel has also determined that it will disclose, by means of a
press release, when The 1818 Fund has tendered its Preferred Stock, and, if
necessary, will extend the Offer for at least five business days after such
tender occurs. Disclosure to this effect has been added to Amendment No. 1.
Please see the cover page of the Offer to Exchange contained in Amendment No. 1.

     4. Comment: How will you inform security holders of the results of the
shareholder vote approving the offer? Given the fact that the offer's
consummation is conditioned on the vote, dissemination of supplemental offering
materials and an extension of the offer may be required.

     Response: Z-Tel has advised us that it will announce the results of the
Special Meeting by means of a press release promptly following the Special
Meeting. As indicated by the timeta-

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                                      -3-

ble set forth above, holders of Preferred Stock will then have five business
days before the expiration of the Offer to decide whether to tender. Disclosure
to this effect has been added to Amendment No. 1. Please see the cover page of
the Offer to Exchange contained in Amendment No. 1.

     5. Comment: Address supplementally whether this offer represents the first
step in a going private transaction. In this regard, we note that ownership of
your common stock by officers and directors as a group will increase from 44.35%
before the offer to 73.01% after, which presumably may at some affect its
liquidity and possibly also the exchange listing.

     Response: Z-Tel has advised us that the Exchange Offer is not related to
any going private transaction and that, as disclosed, one of its reasons for
proceeding with the Exchange Offer is to maintain the listing of the Common
Stock on the Nasdaq SmallCap Market. Please also note that directors and
officers as a group will own 47.60% of the pro forma Common Stock on the basis
presented in the Offer to Exchange, an increase of only 3.25% over the actual
beneficial ownership as of September 27, 2004. Please see the last column of the
table under "Security Ownership" on page 44 of the Offer to Exchange contained
in Amendment No. 1.

Calculation of Filing Fee, cover page

     6. Comment: It is not clear to us how you calculated the fee for this
filing. Provide a breakdown of the transaction valuation for all of the
securities subject to the offer. Keep in mind that since the offer is for any
and all securities, the fee should be calculated based on the value of the
exchange of all the securities in the offer.

     Response: Attached to this letter as Annex A is a spreadsheet that details
Z-Tel's calculation of the filing fee.

Offer to Exchange, cover page

     7. Comment: Refer to the expiration date in the first paragraph on the
cover page. Rule 13e-4(f)(1) requires that the issuer tender offer remain open
for at least twenty business days. Rule 13e-4(a)(3) defines "business day" as
the time period between 12:01 am and 12:00 midnight Eastern time. Since October
11, 2004 was not a business day, your offer does not comply with the time period
mandated by Rule 13e-4(f)(1) and must be extended.

     Response: The Offer has been extended in Amendment No. 1 to November 23,
2004. Please see the cover page of the Offer to Exchange contained in Amendment
No. 1.

Important Information Regarding the Offer, page I

     8. Comment: You state that by tendering, security holders are representing
that their decision to tender is based solely on this Offer to Exchange and
their examination of the company and the terms of the proposed exchange. How can
you ask security holders to certify that they

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did not consider their own specific financial and other conditions in making the
decision to tender? Please revise.

     Response: The representation has been removed from the Offer to Exchange
contained in Amendment No. 1.

     9. Comment: We note that the exchange is being offered in reliance on the
exemption contained in Section 3(a)(9) of the Securities Act of 1933.
Supplementally confirm to us that all of the requirements of that section,
including the requirement that no consideration be paid with respect to the
solicitation, have been met. In this regard, even though you will not be a
soliciting dealer fee for soliciting the preferred shares that are the subject
of this offer, will you engage a proxy solicitor to assist with the accompanying
shareholder vote that is a condition to the offer? If so, how does this factor
into the Section 3(a)(9) analysis?

     Response: Z-Tel and we believe that all requirements of Section 3(a)(9)
have been met, including the requirement that no consideration be paid with
respect to the solicitation. Z-Tel does plan to engage a proxy solicitation
agent, but only with respect to its holders of Common Stock. In general the
proxy solicitation agent is expected to provide only ministerial services. The
proxy solicitation agent will be specifically instructed not to solicit any
holders of Preferred Stock, which Z-Tel will identify to it. Accordingly, the
use of a proxy solicitation agent as contemplated does not affect Z-Tel's or our
Section 3(a)(9) analysis.

     10. Comment: From our telephone conversation today, I understand that
accrued but unpaid dividends on the preferred shares have been added to the
liquidation preference of each class of securities. Explain supplementally why
you believe this treatment of dividends is acceptable under Section 3(a)(9). You
should also revise the disclosure in the offer materials concerning those
accrued but unpaid dividends that is apparently inaccurate.

     Response: The Offer does not require that any holder of Preferred Stock
contribute any consideration other than such holder's shares of Preferred Stock.
Holders of Preferred Stock have no mature right to receive cash or any other
item of value in respect of accrued dividends, which by the terms of each series
of Preferred Stock are added to the liquidation preference of such series.
Holders of Preferred Stock should not be deemed to be contributing new
consideration in respect of a hypothetical possibility of receiving cash in
respect of their Preferred Stock at some future point.

Forward Looking Statements, page i

     11. Comment: We note your reference to the Private Securities Litigation
Reform Act of 1995. The Act does not apply to statements made in connection with
a tender offer. See Sec. 21E(b)(2)(C) of the Securities Exchange Act of 1934.
Revise your schedule TO to clearly acknowledge this, and do not refer to the
Private Securities Litigation Reform Act of 1995 in future communications.

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     Response: This section has been removed from the Offer to Exchange
contained in Amendment No. 1.

Summary Term Sheet, page 1

     12. Comment: We note your disclosure that the offer will qualify as a
tax-free reorganization for federal income tax purposes. Since this represents a
legal conclusion, did you get a tax opinion? If so, please include the name of
the law firm here and file the opinion as an exhibit to the Schedule TO. See
Item 1016(h) of Regulation M-A.

     Response: Amendment No. 1 contains disclosure that Z-Tel did not receive a
tax opinion with respect to whether the Offer will qualify as a tax free
reorganization for federal income tax purposes, but reached its conclusions
based on discussions with its counsel. Please see pages 4 and 41 of the Offer to
Exchange contained in Amendment No. 1.

     13. Comment: The manner in which you treat the accrued but unpaid dividends
on the preferred shares for tax purposes appears to be counter to the way you
treat them for the Section 3(a)(9) analysis. Please explain why this is
appropriate.

     Response: The constructive dividend possibly deemed to exist for tax
purposes does not change Z-Tel's view as to the treatment of accrued dividends
for purposes of Section 3(a)(9). Z-Tel believes that the tax law contains
numerous examples of circumstances under which a taxpayer has a taxable income
without having a right to receive any item value. Original issue discount is a
common example of this, where a holder of a security may be deemed to have
current income in respect of the difference between the issue price of a
security and the amount payable in respect of such security at its maturity in
some future year, even though the holder of such a security is only entitled to
receive interest payments in the current year. In the Offer, not unlike holders
of original issue discount securities, participating holders of Preferred Stock
have no present right to receive anything other than Common Stock, but may be
deemed to have taxable income none the less.

     Finally, it is not certain that holders of Preferred Stock will have any
constructive dividend for tax purposes, and if so, it is not certain that the
amount of any such constructive dividend will equal the actual accrued dividend.
This demonstrates the fundamentally different way the tax code and the Preferred
Stock determine what constitutes a "dividend."

Risk Factors, page 9
We may experience volatility in our stock price that
could affect your investment, page 18

     14. Comment: Refer to the disclosure that the completion of the offer will
result in a single shareholder controlling "a significant amount of our common
stock." Name the shareholder director and quantify the amount of common stock
this person will own if he or she exchanges all of their stock.

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     Response: Z-Tel has added disclosure to this risk factor in Amendment No. 1
in response to this comment. Please see page 19 of the Offer to Exchange
contained in Amendment No. 1.

The Offer to Exchange, page 22

     15. Comment: In your description of the number of shares to be exchanged,
describe the reverse stock split and its impact on the number of shares to be
exchanged in the offer. If the reverse stock split is conditional, describe the
conditions.

     Response: Z-Tel has added disclosure in Amendment No. 1 in response to this
comment. Please see page 24 of the Offer to Exchange contained in Amendment No.
1.

     16. Comment: In your description of the results of the offer, include the
percentage of common shares that the current stockholders presently own.

     Response: Z-Tel has added disclosure in Amendment No. 1 in response to this
comment. Please see pages 24 and 25 of the Offer to Exchange contained in
Amendment No. 1.

Procedures for Tendering Preferred Shares, page 24

     17. Comment: We note your disclosure that you may waive any condition of
the offer for any particular tendering shareholder. Reserving the right to waive
a condition of the offer as to only particular tendering shareholders raises
issues under Rule 13e-4(f)(8) and other wise. Please revise here and throughout
the offer to purchase, where similar language appears.

     Response: Z-Tel has revised this language in Amendment No. 1 to reflect
that if it waives a condition for one holder of Preferred Stock, it will waive
such condition for all holders of Preferred Stock. Please see page 26 of the
Offer to Exchange contained in Amendment No. 1.

Conditions, page 25

     18. Comment: We note that many of the offer conditions listed are broadly
drafted. Whether or not an offer condition has been "triggered" is necessarily a
subjective determination that you st