Marketing Materials for
Cumberland Mountain Bancshares, Inc.
Middlesboro, Kentucky

Table of Contents
-----------------

I. Press Release
A. Explanation
B. Schedule
C. Distribution List
D. Press Release Examples

II. Advertisements
A. Explanation
B. Schedule
C. Advertisement Examples

III. Question and Answer Brochure
A. Explanation
B. Method of Distribution
C. Example

IV. Officer and Director Brochure
A. Explanation
B. Method of Distribution
C. Example

V. IRA Mailing
A. Explanation
B. Quantity
C. IRA Mailing Example

VI. Counter Cards and Lobby Posters
A. Explanation
B. Quantity

VII. Invitations
A. Explanation
B. Quantity - Method of Distribution
C. Examples

VIII. Letters
A. Explanation
B. Method of Distribution
C. Examples

IX. Proxygram
A. Explanation
B. Example

I. Press Releases

A. Explanation

In an effort to assure that all customers, community members and other
interested investors receive prompt accurate information in a simultaneous
manner, Trident advises the Bank to forward press releases to area
newspapers, radio stations, etc. at various points during the conversion
process.

Only press releases approved by Conversion Counsel and the OTS will be
forwarded for publication in any manner.

B. Schedule

1. OTS Approval of Conversion

2. Close of Stock Offering

National and Local Distribution List
------------------------------------

The Bank should provide a supplemental distribution list which includes all
local newspapers that it considers to be within their market area.

(TO BE PROVIDED)

Press Release FOR IMMEDIATE RELEASE
---------------------
For More Information Contact:
James J. Shoffner
(606) 248-4584

MIDDLESBORO FEDERAL BANK, FEDERAL SAVINGS BANK
----------------------------------------------

REORGANIZATION FROM MUTUAL HOLDING COMPANY TO STOCK
---------------------------------------------------

HOLDING COMPANY APPROVED
-------------------------

James J. Shoffner, President of Middlesboro Federal Bank, Federal Savings
Bank (the "Bank"), Middlesboro, Kentucky, announced today that the Bank has
received approval from the Office of Thrift Supervision of the U. S. Department
of the Treasury to reorganize from the mutual holding company form of
organization to the stock holding company form of organization. In connection
with the reorganization, the Bank has formed a new stock company, Cumberland
Mountain Bancshares, Inc. (the "Company"), to serve as the stock holding company
of the Bank.

Pursuant to a plan of conversion and agreement and plan of reorganization,
the Company is offering up to 382,375 shares, subject to adjustment of its
common stock, at a price of $10.00 per share. Certain depositors and borrowers
as of specified record dates, the Company's Employee Stock Ownership Plan,
directors, officers and employees and public stockholders of the Bank will have
an opportunity to purchase stock through a Subscription Offering that will close
on __________, 1997. Stock may be offered to the general public in a Community
Offering with first preference given to natural persons who reside in Bell and
Harlan Counties, Kentucky. The Subscription Offering and the Community Offering
(together, the "Offering") will be managed by Trident Securities, Inc. of
Raleigh, North Carolina. In addition, public

stockholders of the Bank as of the effective date of the reorganization will
receive shares of common stock in the Company in exchange for their common
shares of the Bank at an exchange ratio specified in the Prospectus. Offering
Materials describing, among other things, the terms of the Offering will be
mailed to certain customers and stockholders of the Bank and certain local
community members on or about __________, 1997.

As a result of the reorganization, the Bank will operate as a subsidiary of
the Company. According to Mr. Shoffner, "Our day to day operations will not
change as a result of the reorganization and deposits will continue to be
insured by the FDIC up to the applicable legal limits."

Customers or stockholders with questions concerning the reorganization
should call the Conversion Center at (606) ________________, or visit the Bank's
main office at 1431 Cumberland Avenue, Middlesboro, Kentucky.

This is neither an offer to sell nor a solicitation of an offer to buy the stock
of Cumberland Mountain Bancshares, Inc. The offer is made only by the
Prospectus. The shares of Common Stock are not deposits or savings accounts and
will not be insured by the Federal Deposit Insurance Corporation or any other
---
government agency.

Press Release FOR IMMEDIATE RELEASE
---------------------
For More Information Contact:
James J. Shoffner
(606) 248-4584

CUMBERLAND MOUNTAIN BANCSHARES, INC. COMPLETES STOCK OFFERING
-------------------------------------------------------------

Middlesboro, Kentucky - (________, 1997) James J. Shoffner, President of
Middlesboro Federal Bank, Federal Savings Bank (the "Bank"), announced today
that Cumberland Mountain Bancshares, Inc. (the "Company"), the proposed stock
holding company for the Bank, will complete its initial stock offering on
_________, 1997, in connection with the Bank's conversion from the mutual
holding company corporate structure to the stock holding company corporate
structure. ___________ shares were sold at $10.00 per share in connection with
the stock offering, and _____________ shares are expected to be issued in
exchange for shares of common stock of the Bank.

On______________, 1997, the Bank's Plan of Conversion and Agreement and
Plan of Reorganization was also approved by the voting members of Cumberland
Mountain Bancshares, M.H.C. and the stockholders of the Bank at a Special
Meeting of Members and a Special Meeting of Stockholders, respectively.

Mr. Shoffner indicated that the officers and board of directors of the
Company and the Bank want to express their thanks for the response to the stock
offering and that the Bank looks forward to serving the needs of its customers
and new stockholders as a community-based stock institution. The offering was
managed by Trident Securities, Inc. The stock will be traded on the over-the-
counter market through the OTC, "Electronic Bulletin Board" under the symbol
"CMBN" commencing on ________, 1997.

II. Advertisements

A. Explanation

The intended use of the attached advertisement "A" is to notify the Bank's
customers, stockholders and members of the local community that the
conversion offering is underway.

The intended use of advertisement "B" is to remind the Bank's customers and
stockholders of the closing date of the subscription offering.

B. Media Schedule

1. Advertisement A - To be run immediately following OTS approval and run
weekly for the first three weeks.
2. Advertisement B - To be run during the last week of the subscription
offering.

Trident may feel it is necessary to run more ads in order to remind
customers, stockholders and community members of the close of the
Subscription/Community Offering.

Alternatively, Trident may, depending upon the response from the customer
and stockholder base, choose to run fewer ads or no ads at all.

Advertisement (A)

This announcement is neither an offer to sell nor a solicitation of an offer
to buy these securities. The offer is made only by the Prospectus. These shares
have not been approved or disapproved by the Securities and Exchange Commission,
the Office of Thrift Supervision or the Savings Association Insurance Fund of
the Federal Deposit Insurance Corporation, nor has such commission, office or
corporation passed upon the accuracy or adequacy of the prospectus. Any
representation to the contrary is unlawful.

New Issue _______, 1997
- ---------

382,375 Shares

These shares are being offered pursuant to a
Plan of Conversion and Agreement and Plan of Reorganization whereby

Middlesboro Federal Bank,
Federal Savings Bank

Middlesboro, Kentucky will
convert from the mutual holding company form of organization
to a federal stock holding company form of organization
and become a wholly-owned subsidiary of

Cumberland Mountain Bancshares, Inc.

Common Stock

---------------

Price $10.00 Per Share

---------------

Trident Securities, Inc.

For a copy of the prospectus call (606) ________.

Copies of the Prospectus may be obtained in any State in which this announcement
is circulated from the undersigned or such other brokers and dealers as may
legally offer these securities in such state.

Advertisement (B)

MIDDLESBORO FEDERAL BANK'S CUSTOMERS, STOCKHOLDERS
AND MEMBERS OF THE GENERAL PUBLIC

_____________, IS THE DEADLINE TO
ORDER STOCK OF CUMBERLAND MOUNTAIN BANCSHARES, INC.

Shareholders and certain customers of Middlesboro Federal Bank,
Federal Savings Bank (the "Bank") and members of the general public have the
opportunity to invest in the Bank by subscribing
for common stock in its proposed stock holding company
CUMBERLAND MOUNTAIN BANCSHARES, INC.

A Prospectus relating to these securities is
available at our office or by calling our
Stock Information Center at (606) _____________.

This announcement is not an offer to sell or a solicitation of an offer to
buy the stock of Cumberland Mountain Bancshares, Inc. The offer is made only by
the Prospectus. The shares of Common Stock are not deposits or savings accounts
and will not be insured by the Federal Deposit Insurance Corporation or any
other government agency.

III. Question and Answer Brochure

A. Explanation

The Question and Answer brochure is an essential marketing piece in any
conversion. It serves to answer some of the most commonly asked questions
in "plain, everyday language". Although most of the answers are taken
verbatim from the Prospectus, it saves the individual from searching for
the answer to a simple question.

B. Method of Distribution

There are four primary methods of distribution of the Question and Answer
brochure. However, regardless of the method the brochures are always
accompanied by a Prospectus.

1. A Question and Answer brochure is sent out in the initial mailing to
all members and stockholders of the Bank.

2. Question and Answer brochures are available at the Bank.

3. Question and Answer brochures are distributed in information packets
at community meetings.

4. Question and Answer brochures are sent out in a standard information
packet to all interested investors who phone the Stock Information
Center requesting information.

QUESTIONS AND ANSWERS
REGARDING
THE PLAN OF CONVERSION

On December 12, 1996, the Boards of Directors of Middlesboro Federal Bank,
Federal Savings Bank (the "Bank"), Cumberland Mountain Bancshares, M.H.C. (the
"Mutual Holding Company") and Cumberland Mountain Bancshares, Inc. (the
"Company") unanimously adopted the Plan of Conversion and Agreement and Plan of
Reorganization (the "Plan") pursuant to which the Mutual Holding Company will
convert from mutual to stock form and the Bank will reorganize as a wholly-owned
subsidiary of the Company.

This brochure is provided to answer basic questions regarding the
Conversion and Reorganization (herein after defined). Following the Conversion
and Reorganization, the Bank will continue to provide financial services to its
depositors, borrowers and other customers and will operate with its existing
management and employees. The Conversion and Reorganization will not affect the
terms, balances, interest rates or existing federal insurance coverage on the
Bank's deposits or the terms or conditions of any loans to existing borrowers
under their individual contract arrangements with the Bank.

For complete information regarding the Conversion and Reorganization, see
the Prospectus dated _________________, 1997. Copies of the Prospectus may be
obtained by calling the Conversion Center at (606) ________________________.

Background
- ----------

In 1994, the Bank reorganized into the mutual holding company structure.
In connection with this transaction, the Mutual Holding Company was formed, and
the Bank became a public company through an offering of its common stock.

The primary business of the Mutual Holding Company has been to hold shares
of the Bank's common stock (the "Bank Common Stock"). As majority shareholder
of the Bank, the Mutual Holding Company holds 330,000 shares or 64.71% of the
outstanding shares of Bank Common Stock. The remaining shares (the "Public Bank
Shares") are traded publicly. They are owned by the Bank's management,
customers and members of the general public (collectively, the "Public
Stockholders").

In connection with the Conversion and Reorganization, the Company intends
to issue up to 382,375 shares (which may be increased to 439,731 shares) of
Company common stock (the "Conversion Stock") at a purchase price of $10.00 per
share (the "Purchase Price") in a Subscription Offering and Community Offering,
if needed, and, if necessary, a Syndicated Community Offering (collectively, the
"Offerings"). In addition the shares of the Bank Common Stock held by the
Public Stockholders as of the effective date of the Conversion and
Reorganization (the "Effective Date") will be converted into shares of Company
common stock (the "Exchange Shares") at a stated Exchange Ratio (the
"Exchange"). The Public

Stockholders will be mailed instructions with regard to effecting the Exchange.
The Conversion of the Mutual Holding Company, the Offerings and the Exchange are
referred to collectively herein as the "Conversion and Reorganization." As
required by Office of Thrift Supervision regulations, members of the Mutual
Holding Company and the Bank's stockholders are being asked to approve the Plan
as addressed below in the section entitled "Voting."

1. Q. What will be the effect of the Conversion and Reorganization?

A. * The Company will replace the Mutual Holding Company as the holding
company for the Bank.

* The Public Stockholders will receive common stock of the Company
in exchange for their Bank Common Stock.

* The Company's common stock will be publicly held and will be
traded on the over-the-counter "Electronic Bulletin Board" under
the symbol "CMBN."

* The Company will issue shares of common stock.

2. Q. What is the reason for the Conversion and Reorganization?

A. In 1994, the Bank reorganized into the mutual holding company structure
for a number of reasons, including the ability to raise capital on an
incremental basis so that new capital could be invested in a controlled
manner. If the Bank had undertaken a standard conversion involving the
formation of a stock holding company in 1994, applicable Office of
Thrift Supervision regulations would have required a greater amount of
common stock to be sold, resulting in more proceeds than could not have
been effectively utilized at the time.

A principal purpose of the Conversion and Reorganization is to
structure the Company in the stock form of organization which is used
by most other holding companies of savings institutions and commercial
banks. This structure, along with the increased capital resulting from
the Offerings, will facilitate possible diversification into other
banking-related businesses and will provide the Company with additional
flexibility.

Additionally, the Conversion and Reorganization will result in an
increase in the number of outstanding shares of common stock which will
increase the likelihood of the development of a more active and liquid
trading market.

The Board of Directors believes that the conversion of the Mutual
Holding Company from the mutual to the stock form of organization and
the related Offerings and Exchange are consistent with the goal of
enhancing value for stockholders and customers.

3. Q. Will the Conversion and Reorganization have any effect on my
savings account or loan account with the Bank?

A. No. Customers will be served in the same offices by the same staff. The
Conversion and Reorganization will not affect the amount, interest rate
or withdrawal rights of deposit accounts, which will continue to be
insured by the Savings Association Insurance Fund of the Federal
Deposit Insurance Corporation to the maximum legal limit. Likewise, the
loan accounts and rights of borrowers will not be affected.

4. Q. Will there be changes in directors, officers or employees as a
result of the Conversion and Reorganization?

A. No. Officers and employees of the Bank will continue in their current
capacities. The directors of the Bank will serve as the initial
directors of the Company.

5. Q. Does the Company anticipate paying cash dividends on the Company's
common stock?

A. While the Company will consider the establishment of a dividend policy
following the Conversion and Reorganization, there is no current
intention to pay dividends. The Board will review its dividend policy
on a quarterly basis. The Company's ability to pay dividends in the
future will depend on the net proceeds retained from the Offerings and
on dividends received from the Bank, which is subject to various
regulatory restrictions on the payment of dividends.

6. Q. How will the proceeds of the Offerings be used?

A. Net proceeds from the sale of the Conversion Stock are estimated to be
between $2.5 million and $3.5 million. The Company plans to
contribute to the Bank all but $100,000 of the net proceeds from the
Offerings (after deduction of the amount necessary to fund the
Company's Employee Stock Ownership Plan (the "ESOP")) and retain the
remainder of the net proceeds. The Company intends to make a loan
directly to the ESOP to enable it to purchase 3.0% of the common
stock. The net proceeds retained by the Company will initially be to
invested in short-term interest-bearing deposits and marketable
securities. Funds retained by the Company may be used to support the
future expansion of operations and for other business or investment
purposes, including the acquisition of other financial institutions
and/or branch offices, although there are no current plans,
arrangements, understandings or agreements regarding such expansion or
acquisitions. Subject to applicable limitations, such funds also may
be used in the future to repurchase shares of common stock. Funds
contributed to the Bank from the Company will be used for general
business purposes. The proceeds will be used to support the Bank's
lending and investment activities and thereby enhance the Bank's
capabilities to service the borrowing and other financial needs of the
communities it serves.

VOTING - YOUR VOTE IS IMPORTANT

The Mutual Holding Company's Members (as defined below) are being asked to
approve the Plan, which was adopted by the Boards of Directors of the Bank, the
Mutual Holding Company and the Company and approved by the Office of Thrift
Supervision. The Bank's and Agreement and Plan of Reorganization shareholders
are also being asked to approve the Plan. A copy of the Plan of Conversion may
be obtained from any Bank office or by calling the Conversion Center.

Voting on the Plan does not affect deposit or loan accounts at the Bank, and
does not obligate customers or shareholders to purchase stock in the Offerings.

7. Q. Which customers of the Bank are being asked to vote on the Plan?

A. Depositors of the Bank as of _____________, 1997 and borrowers of the
Bank as of __________ who continue to be borrowers as of ___________,
1997 (the "Members"). The Members have been provided with Proxy Cards
and Proxy Statements describing the Plan.

Each depositor Member will be entitled to cast one vote for each $100
or fraction thereof of the withdrawable value of any savings accounts
in the Bank as of _____________, 1997. Each borrower Member will be
entitled to cast one vote, in addition to any number of votes to which
such Member is entitled to as holder of a savings account. The maximum
number of votes eligible to be cast by a Member may not exceed 1,000.
The affirmative vote of a majority of the total votes eligible to be
cast is required for approval of the Plan.

In accordance with Office of Thrift Supervision regulations, Members
are being solicited to vote. The Board of Directors urges Members to
vote FOR the Plan. Not voting will have the same effect as a vote
against the Plan. Without sufficient favorable votes, the Conversion
and Reorganization cannot be completed. In that event, funds submitted
by investors in connection with the Offerings would be promptly
returned, with interest.

8. Q. Which stockholders of the Bank may vote on the Plan?

A. Public Stockholders of the Bank as of __________, 1997. These
stockholders have been provided with a Proxy Statement describing the
Plan of Conversion and Reorganization and have also received Proxy
Cards. The affirmative vote of at least a majority of the votes cast by
Public Stockholders and two thirds of the outstanding Bank Common Stock
(including shares held by the Mutual Holding Company) is required for
approval of the Plan. The Board of Directors urges stockholders to vote
FOR the Plan.

9. Q. How do I vote by proxy?

A. Please read the Proxy Statement that you received. You may vote by
completing, signing and returning the Proxy Card in the Proxy Return
Envelope provided. Please respond promptly.

10. Q. Why may I have received several Proxy Cards?

A. If you have more than one deposit or loan account at the Bank, you
could receive more than one informational packet and each packet should
-----
contain a separate Proxy Card, depending on the ownership structure of
your accounts.

If you owned shares of the Bank Common Stock under more than one
registration, you will receive more than one informational packet and
each packet should contain a separate Proxy Card. PLEASE VOTE, SIGN AND
PROMPTLY RETURN ALL PROXY CARDS.

11. Q. Am I obligated to purchase stock if I vote in favor of the Plan?

A. No. To purchase stock in the Offerings, you must place an order and
make a payment.

THE OFFERINGS

Investment in common stock involves certain risks. Before making an investment
decision, please carefully read the enclosed Prospectus, including the section
entitled "Risk Factors."

12. Q. Who may purchase Conversion Stock in the Offerings?

A. The Offerings consist of (i) a Subscription Offering to certain past
and current customers of the Bank, the ESOP, directors, officers and
employees of the Mutual Holding Company and the Bank and the Public
Stockholders and (ii) Community Offering, if needed, to certain members
of the general public, with preference given to natural persons
residing in Bell and Harlan Counties, Kentucky.

The Conversion Stock is being offered in the following order of
priority: (i) depositors of the Bank with account balances of $50.00 or
more as of the close of business on September 30, 1995 ("Eligible
Account Holders"); (ii) the ESOP; (iii) depositors of the Bank with
account balances of $50.00 or more as of the close of business on
December 31, 1996 ("Supplemental Eligible Account Holders"); (iv)
depositors of the Bank as of the close of business on _________, 1997
(other than Eligible Account Holders and Supplemental Eligible Account
Holders) ("Other

Members"); (v) directors, officers and employees of the Bank; and (vi)
Public Stockholders.

To the extent that share remain available for purchase, a Community
Offering, if any, may commence without notice at any time after the
commencement of the Subscription Offering and may terminate at any time
without notice but may not terminate later than _______, 1997. The
right of any person to purchase shares in the Community Offering, if
any, is subject to the absolute right of the primary parties to accept
or reject such purchases in whole or in part. Preference will be given
in the Community Offering to permanent residents of Bell and Harlan
Counties, Kentucky.

13. Q. What is the price per share?

A. The shares of Conversion Stock are being offered at a Purchase Price of
$10.00 per share. All subscribers will pay the same price per share. No
commission will be charged.

14. Q. How was the offering range and Purchase Price of the Conversion Stock
determined?

A. Federal regulations require that the aggregate purchase price of the
---------
common stock in the Offerings be consistent with an independent
appraisal of the pro forma value of the Bank and the Company. The
appraisal, dated December 13, 1996 was conducted by RP Financial, LC.,
a firm experienced in valuations of financial institutions. The
appraisal indicated an estimated aggregate pro forma market value of
$5,100,000 (the "Independent Valuation"). Because the Public
Stockholders will continue to hold the same aggregate percentage
ownership interest in the Company as they hold in the Bank, the
Appraisal was multiplied by the Mutual Holding Company's percentage
interest in the Bank to determine the midpoint of the valuation price
range (the "Valuation Price Range"), of $3,325,000. The Board of
Directors of the Mutual Holding Company, the Bank and the Company have
determined to offer the common stock at a purchase price of $10.00 per
share. Based on this price and the independent valuation, the Company
is offering a range of between approximately $2,826,250 and $3,823,750
of common stock, or between 282,625 shares and 382,375 shares of common
stock, subject to a potential 15% increase to 439,731 shares. An
additional 3% of shares may be sold to the ESOP, under certain
circumstances.

Upon consummation of the Conversion and Reorganization, shares issued
in the Offerings will represent approximately 64.71% of shares
outstanding, while shares issued pursuant to the Exchange will
represent approximately 35.29% of outstanding shares. Assuming the sale
of 332,500 shares, the midpoint of the Valuation Price Range, it is
anticipated that there will be 513,863 shares of common stock

outstanding upon consummation of the Conversion and Reorganization
including shares to be issued in the Exchange.

The Independent Valuation will be updated at the conclusion of the
Offerings. In the event that less than 282,625 shares are sold in the
Offerings, a resolicitation of subscribers may be necessary.
Resolicitation will also be necessary in the event that more than
439,731 shares are issued in the Offerings (although an additional 3%
of shares may be sold to the ESOP, without a resolicitation of
subscribers).

15. Q. When does the Subscription Offering and, if any, the Community
Offering terminate?

A. The Subscription Offering will terminate at 12:00 p.m. Eastern Time, on
__________, 1997, unless the Offerings are extended. The Community
Offering may not terminate later than ______, 1997.

16. Q. How do I purchase Conversion Stock in the Offerings?

A. Please carefully read and complete the Stock Order Form. The Bank is
not required to accept copies of Stock Order Forms. You may hand
deliver the Stock Order Form to any Bank office, or you may use the
enclosed Order Form Reply Envelope. Your stock order form must be
received by the Bank no later than 12:00 PM, Eastern time on
__________, 1997. Payment may be made by check or money order or by
authorization of withdrawal from your Bank passbook or certificate of
deposit account(s). A hold will be placed on the designated account(s)
for the authorized amount(s). Withdrawal will be made at the
consummation of the Conversion and Reorganization. Any applicable
penalty for early withdrawal will be waived.

17. Q. Will I receive interest on funds I submit?

A. Yes. Funds received will be placed in a segregated account at the Bank,
and interest will be paid at the Bank's passbook rate until the
Offerings are consummated. With respect to authorized account
withdrawals, interest will continue to accrue at the account's
contractual rate until the Offerings are consummated.

18. Q. How may I purchase the common stock through a Bank IRA?

A. If you have an IRA at the Bank, you will need to transfer your existing
relationship to an independent trustee authorized to hold self-directed
IRA accounts. Please call the Conversion Center for assistance in
transferring your account or establishing a new self-directed IRA for
the purchase of stock. Because IRA-related procedures take time, you
must contact the Conversion Center by ______, 1997 to facilitate your
request.

19. Q. What is the minimum and maximum number of shares that I may subscribe
for in the Offerings?

A. The minimum purchase is 25 shares. No person or entity, together with
associates and persons acting in convert, may, directly or indirectly
subscribe for or purchase in the Offerings more than 5.0% of the total
number of shares offered (19,118 shares at the maximum of the Valuation
Price Range).

20. Q. What will happen to my order if orders are received for more stock
than is available?

A. In the event of an oversubscription, shares will be allocated according
to federal regulations and the Plan of Conversion.

Because qualifying deposits are utilized in allocating shares, each
Eligible Account Holder and Supplemental Eligible Account Holder should
be sure to list on the Stock Order Form all deposit accounts in which
he or she had an ownership interest at the applicable date, September
30, 1995 or December 31, 1996.

21. Q. Will the Company's common stock be insured by the Federal Deposit
Insurance Corporation?

A. No. Stock cannot be insured by the Federal Deposit Insurance
Corporation.

22. Q. Are directors and officers purchasing conversion stock in the
Offerings?

A. Yes. In the Offerings, they expect to purchase an aggregate of _______
shares. After exchange of their Bank common stock for Company common
stock, directors and executive officers are expected to own _____% of
the outstanding common stock of the Company, assuming the sale of
___________ shares in the Offerings.

23. Q. When will I receive my stock certificate for shares I purchased in
the Offerings?

A. Stock certificates will be mailed as soon as practicable after the
Offerings are consummated. Please be aware that you may not be able to
sell the shares you purchased until you have received a stock
certificate.

24. Q. How may I purchase or sell shares in the future?

A. You may purchase or sell shares through a stockbroker. The Company
anticipates that the Common Stock will be traded on the over-the-
counter market through the OTC "Electronic Bulletin Board" under the
symbol "CMBN." It is expected that the Company's common stock will be
more liquid than the Bank's common stock has been, because there will
be a significantly larger number of shares owned by the public. There
can be no assurance, however, that an active and liquid market for the
common stock will develop or be maintained.

THE EXCHANGE

Upon the Effective Date, trading in the Bank Common Stock will cease. Each
Public Stockholder as of the Effective Date will be contacted for the purpose of
exchanging Public Bank Shares for shares of Company common stock. Please refer
to the Prospectus for a detailed discussion of the Exchange.

25. Q. What is the Exchange?

A. Each share of Bank Common Stock owned by Public Stockholders on the
Effective Date will automatically be converted into shares of the
Company's common stock pursuant to an exchange ratio ("Exchange
Ratio").

26. Q. How was the Exchange Ratio determined?

A. The Exchange Ratio was derived to ensure that each Public Stockholder
will own approximately the same percentage of the Company's common
stock as he owned of the Bank's Common Stock. The Public Stockholders
currently own 35.29% of the Bank Common Stock. Based on this percentage
and on the midpoint of the offering range of 332,500 shares, the
Exchange Ratio is expected to be 1.008 shares, of the Company's common
stock for each share of the Bank's Common Stock. If the offering range
is increased to 15% above the maximum to 439,731 shares, the Exchange
Ratio would increase to 1.333.

27. Q. How will the Exchange be accomplished?

A. As of the Effective Date, the shares of the Bank Common Stock held by
the Mutual Holding Company will be canceled, and the shares of Bank
Common Stock owned by Public Stockholders will no longer be accepted
for transfer on the Bank's books. As soon as practicable, the Bank will
send transmittal forms to Public Stockholders. The transmittal forms
are expected to be mailed promptly following the Effective Date and
will contain instructions with respect to the surrender of certificates
representing the Bank Common Stock to be exchanged for the Company's
common stock. It is expected that certificates for shares of the
Company's common stock will be distributed promptly after receipt of
the properly executed transmittal forms. Cash will be issued in lieu of
fractional shares.

Stockholders should not forward certificates until they receive
instructions.

MUTUAL TO STOCK CONVERSION
--------------------------

28. Q. How can I get further information concerning the Conversion?

A. You may call the Stock Information Center at (606) __________________
for further information or to request a copy of the Prospectus, a Stock
Order Form or a Proxy Card.

THIS INFORMATION DOES NOT CONSTITUTE AN OFFER TO SELL NOR A SOLICITATION OF
AN OFFER TO BUY CUMBERLAND MOUNTAIN BANCSHARES, INC. COMMON STOCK. OFFERS TO
BUY OR TO SELL MAY BE MADE ONLY BY THE PROSPECTUS. PLEASE READ THE PROSPECTUS
PRIOR TO MAKING AN INVESTMENT DECISION. COPIES OF THE PROSPECTUS MAY BE
OBTAINED BY CALLING THE CONVERSION CENTER AT (606) _______________.

THE SHARES OF CUMBERLAND MOUNTAIN BANCSHARES, INC. COMMON STOCK BEING
OFFERED IN THE OFFERINGS ARE NOT SAVINGS OR DEPOSIT ACCOUNTS AND ARE NOT INSURED
BY THE SAVINGS ASSOCIATION INSURANCE FUND OF THE FEDERAL DEPOSIT INSURANCE
CORPORATION OR ANY OTHER GOVERNMENTAL AGENCY.

IV. Officer and Director Support Brochure

A. Explanation

An Officer and Director Brochure merely highlights in brochure form the
investment commitments shown in the Prospectus.

B. Quantity

An Officer and Director brochure is proposed to be sent out in the initial
mailing to all customers and stockholders of the Bank along with the
Prospectus.

DIRECTOR AND EXECUTIVE OFFICER
INVESTMENT COMMITMENT

Proposed Purchases of Total Common Stock
Conversion Stock to be Held
---------------- ----------

Number of Number of Percentage
Name Number of Exchange Amount Shares Shares of Total
- ---- Shares to be Held (1) ------ ------ ------ --------

J. Roy Shoffner
Robert R. Long
James J. Shoffner
Reecie Stagnolia, Jr.
Raymond C. Walker
J.D. Howard
Diana Miracle

All directors and
executive officers of
the Bank as a
group (seven persons)

V. IRA Mailing

A. Explanation

A special IRA mailing is proposed to be sent to all IRA customers of the
Bank in order to alert the customers and stockholders that funds held in an
IRA can be used to purchase stock. Since this transaction is not as simple
as designating funds from a certificate of deposit like a normal stock
purchase, this letter informs the customer or stockholder that this process
is slightly more detailed and involves a personal visit to the Bank.

B. Quantity

One IRA letter is proposed to be mailed to each IRA customer or
stockholders of the Bank. These letters would be mailed following OTS
approval for the Conversion and Reorganization and after each customer or
stockholder has received the initial mailing containing a Proxy Statement
and a Prospectus.

C. Example - See following page.

Middlesboro Federal Bank Letterhead

________, 1997

Dear Individual Retirement Account Participant:

As you know, Middlesboro Federal Bank, Federal Savings Bank (the "Bank") is
in the process of converting from the mutual holding company form of
organization and has formed a new stock company, Cumberland Mountain Bancshares,
Inc. (the "Company") to hold all of the stock of the Bank. Through the
conversion, certain current and former customers and stockholders have the
opportunity to purchase shares of common stock of the Company in a Subscription
Offering. The Company currently is offering up to 332,500 shares, subject to
adjustment, of the Company at a price of $10.00 per share.

As the holder of an individual retirement account ("IRA") at the Bank, you
have an opportunity to become a shareholder in the Company using some or all of
the funds being held in your IRA. If you desire to purchase shares of common
stock of the Company through your IRA, the Bank can assist you in self-directing
those funds. This process can be done without an early withdrawal penalty and
generally without a negative tax consequence to your retirement account.

If you are interested in receiving more information on self-directing your
IRA, please contact our Conversion Center at (606) ___________________. Because
it may take several days to process the necessary IRA forms, you must contact
the Conversion Center by _______, 1997 to accommodate your interest.

Sincerely,

James J. Shoffner
President

This letter is neither an offer to sell nor a solicitation of an offer to buy
Cumberland Mountain Bancshares, Inc. Common Stock. The offer is made only by
the Prospectus, which was recently mailed to you. The shares of Cumberland
Mountain Bancshares, Inc. Common Stock are not deposits and will not be insured
---
by the Federal Deposit Insurance Corporation or any other governmental agency.

VI. Counter Cards and Lobby Posters

A. Explanation

Counter cards and lobby posters serve two purposes: (1) As a notice to the
Bank's customers, stockholders and members of the local community that the
stock sale is underway and (2) to remind the customers and stockholders of
the end of the Subscription Offering. Trident has learned in the past that
many people forget the deadline for subscribing and therefore we suggest
the use of these simple reminders.

B. Quantity

Approximately 2 - 3 Counter cards will be used at teller windows and on
customer service representatives' desk.

Approximately 1 - 2 Lobby posters will be used at the office of the Bank

C. Example

C. POSTER
OR
COUNTER CARD

Cumberland Mountain Bancshares, Inc.

Proposed Stock Holding Company for

Middlesboro Federal Bank, Federal Savings Bank

"STOCK OFFERING MATERIALS
AVAILABLE HERE"

Subscription Offering Ends

________, 1997

VII. Invitations

A. Explanation

In order to educate the public about the stock offering, Trident suggests
holding several Community Meetings in various locations. In an effort to
target a group of interested investors Trident requests that each Director
of the Bank submit a list of friends that he would like to invite to a
Community Meeting.

Prospectuses are given to each prospect at the Community meeting.

B. Quantity and Method of Distribution

Each Director submits a list of their prospects. An invitation is mailed
to each director's prospect.

The Directors, Officers & Employees

Middlesboro Federal Bank, Federal Savings Bank

cordially invite you

to attend a brief presentation

regarding the stock offering of

the Bank's proposed stock holding company,

Cumberland Mountain Bancshares, Inc.

Please join us at

Place

Address

Date

at Time

for hors d'oeuvres
R.S.V.P.
(606) _________________

VIII. Letters

A. Explanation

Once the Application for Conversion has been approved by the OTS, Trident
will send out a series of three letters to the Officer's and Director's
targeted prospects. These letters are used to help facilitate the
marketing effort to this group. All prospects will receive a Prospectus as
soon as they are available.

B. Method of Distribution

Each Director submits his list of prospects. Each prospect is sent the
series of three letters all during the Subscription and Community Offering.

C. Examples

1. Introductory letter
2. A. Thank you letter
or
B. Sorry you were unable to attend letter
3. Final reminder letter

Example 1

(Introductory Letter)

(Middlesboro Federal Bank Letterhead)

_______, 1997

Name
Address
City, State, Zip

Dear Name:

You have probably read recently in the newspaper that Middlesboro Federal
Bank, Federal Savings Bank (the "Bank") will soon be converting from the mutual
holding company form of organization to full stock holding company form. This
conversion and reorganization (the "Converson and Reorganization") is the
biggest step in the history of the Bank in that it allows customers, community
members, employees and directors the opportunity to subscribe for stock in our
new holding company - Cumberland Mountain Bancshares, Inc.(the "Company").

I have enclosed a Prospectus and a Stock Order Form which will allow you to
subscribe for shares and possibly become a stockholder of the Company should you
so desire. In addition, we will be holding several presentations for friends of
the Bank in order to review the Conversion and Reorganization and the merits of
becoming a stockholder of the Company. You will receive an invitation shortly.

I hope that if you have any questions you will feel free to call me or the
Bank's Conversion Center at (606) _____________. I look forward to seeing you
at our presentation.

Sincerely,

Director

The shares of Common Stock offered in connection with the conversion are
not savings accounts or deposits and are not insured by the Federal Deposit
Insurance Corporation, the Savings Association Insurance Fund or any other
governmental agency.

This is not an offer to sell nor a solicitation of an offer to buy stock.
The offer will be made only by the Prospectus.

Example 2A

(Thank You Letter)

(Middlesboro Federal Bank Letterhead)

___________, 1997

Name
Address
City, State, Zip

Dear Name:

On behalf of the Board of Directors and management of Middlesboro Federal
Bank, Federal Savings Bank, I would like to thank you for attending our recent
presentation regarding the stock offering of Cumberland Mountain Bancshares,
Inc. We are enthusiastic about the stock offering and look forward to
completing the Subscription Offering and the Community Offering on _______,
1997.

As discussed at our meeting, the Board of Directors and management are
committed to the goal of a profitable future as a local community financial
institution.

I hope that you will join me in being a stockholder, and once again thank
you for your interest.

Sincerely,

James J. Shoffner
President

This is not an offer to sell nor a solicitation of an offer to buy stock.
The offer will be made only by the Prospectus.

Example 2B

(Sorry You Were Unable to Attend)

(Middlesboro Federal Bank Letterhead)

_______________, 1997

Name
Address
City, State, Zip

Dear Name:

I am sorry you were unable to attend our recent presentation regarding
Middlesboro Federal Bank, Federal Savings Bank's (the "Bank") reorganization
from the mutual holding company form of organization to stock form. The Board
of Directors and management are committed to building long term stockholder
value, and as a group we will own approximately ______ shares of Cumberland
Mountain Bancshares, Inc. We are enthusiastic about the stock offering and look
forward to completing the Subscription offering and the Community Offering on
_______, 1997.

We have established a Conversion Center to answer any questions regarding
the conversion and stock offering. Should you require any assistance between
now and _______, I encourage you either to stop by any office of the Bank or to
call our Conversion Center at (606) ____________.

I hope you will join me in becoming a stockholder of Cumberland Mountain
Bancshares, Inc.

Sincerely,

James J. Shoffner
President

This is not an offer to sell or a solicitation of an offer to buy stock.
The offer will be made only by the Prospectus.

Example 3

(Final Reminder Letter)

(Middlesboro Federal Bank Letterhead)

___________, 1997

Name
Address
City, State, Zip

Dear Name:

Just a quick note to remind you that the deadline is quickly approaching
for purchasing stock in Cumberland Mountain Bancshares, Inc., the proposed stock
holding company for Middlesboro Federal Bank, Federal Savings Bank, I hope you
will join me in becoming a stockholder in Kentucky's newest publicly owned
financial institution holding company.

The deadline for subscribing for shares to become a stockholder is _______,
1997. If you have any questions, I hope you will call our Conversion Center at
(606) __________________.

Once again, I look forward to having you join me as a stockholder of
Cumberland Mountain Bancshares, Inc.

Sincerely,

James J. Shoffner
President

This is not an offer to sell or a solicitation of an offer to buy stock.
The offer will be made only by the Prospectus.

IX. Proxygram

A. Explanation

A proxygram is used when the majority of votes needed to adopt the Plan of
Conversion is still outstanding. The proxygram is mailed to those "target
vote" depositors and stockholders who have not previously returned their
signed proxy.

The target vote depositors and stockholders are determined by the
conversion agent and registrar.

B. Example

- --------------------------------------------------------------------------------

P R O X Y G R A M

Middlesboro Federal Bank, Federal Savings Bank

Cumberland Mountain Bancshares, M.H.C.

YOUR VOTE ON OUR PLAN OF CONVERSION AND AGREEMENT AND PLAN OF REORGANIZATION HAS
- --------- ---
NOT BEEN RECEIVED.
- -----------------

YOUR VOTE IS VERY IMPORTANT, PARTICULARLY SINCE FAILURE TO VOTE IS EQUIVALENT TO
- ---------------------------
VOTING AGAINST THE PLAN.

VOTING FOR THE CONVERSION WILL NOT AFFECT THE INSURANCE OF YOUR ACCOUNT. IT
--
WILL CONTINUE TO BE INSURED UP TO $100,000 BY THE FEDERAL DEPOSIT INSURANCE
- ---------------------------------------------------------------------------
CORPORATION.
- -----------

YOU MAY PURCHASE STOCK IF YOU WISH, BUT VOTING DOES NOT OBLIGATE YOU TO BUY
STOCK.

PLEASE ACT PROMPTLY! SIGN THE ENCLOSED PROXY CARD AND MAIL, OR DELIVER, THE
----------------------------
PROXY CARD TO MIDDLESBORO FEDERAL BANK TODAY. PLEASE VOTE ALL PROXY CARDS
---
RECEIVED.

WE RECOMMEND THAT YOU VOTE "FOR" THE PLAN OF CONVERSION AND AGREEMENT AND PLAN
OF REORGANIZATION. THANK YOU.

THE BOARD OF DIRECTORS AND MANAGEMENT OF
MIDDLESBORO FEDERAL BANK AND CUMBERLAND
MOUNTAIN BANCSHARES, M.H.C.

- --------------------------------------------------------------------------------

IF YOU RECENTLY MAILED THE PROXY,
PLEASE ACCEPT OUR THANKS AND DISREGARD THIS REQUEST.
FOR FURTHER INFORMATION CALL (606) __________.