EX-10.5



 Exhibit 10.5 

Execution Version 

PURCHASE AGREEMENT 

This PURCHASE AGREEMENT (this “Agreement”) dated as of September 7, 2016, is entered into by and between ICC Holdings,
Inc., a Pennsylvania corporation (the “Company”), Illinois Casualty Company, an Illinois mutual insurance company (“Illinois Casualty”), and Rock Island Investors, LLC, a Delaware limited liability company (the
“Standby Purchaser”). 
 W I T N E S S E T H: 

WHEREAS, the Company proposes, as soon as practicable after the Registration Statement, as defined herein, becomes effective, to distribute to
Eligible Members, as defined herein, of Illinois Casualty non-transferable rights (the “Rights”) to subscribe for and purchase up to 3,680,000 shares of Common Stock of the Company (the “Shares”) at a subscription
price (the “Subscription Price”) of $10.00 per share (such offering, the “Subscription Offering”) in accordance with the Plan of Conversion, as defined herein, adopted by Illinois Casualty; and 

WHEREAS, contemporaneously with the Subscription Offering, the Company will offer the Shares to the public at the Subscription Price (the
“Community Offering”); and 
 WHEREAS, the Company has requested the Standby Purchaser to agree to purchase from the
Company in the Community Offering upon expiration of the Subscription Offering, and the Standby Purchaser is willing to so purchase at the Subscription Price, up to a certain number of Shares not purchased in connection with the Subscription
Offering; and 
 WHEREAS, the Company has requested that a limited number of other investors (the “Other Standby
Purchasers” and, together with the Standby Purchaser, collectively, the “Standby Purchasers”) to agree to purchase from the Company in the Community Offering upon expiration of the Subscription Offering, and the Other
Standby Purchasers are willing to so purchase at the Subscription Price, up to a certain number of Shares not purchased in connection with the Subscription Offering; 

WHEREAS, each of the Standby Purchasers has a substantive pre-existing relationship with the Company; and 

WHEREAS, the Company may engage Griffin Financial Group, LLC (“Griffin”) and other FINRA member broker-dealers to offer any
of the Shares not sold in the Subscription Offering and the Community Offering to the public in a syndicated offering (the “Syndicated Offering” and together with the Subscription Offering and the Community Offering, the
“Offerings”). 
 NOW THEREFORE, in consideration of the foregoing and the mutual covenants herein contained, and intending
to be legally bound, the parties hereto hereby agree as follows: 
 Section 1. Certain Other Definitions. The following terms
used herein shall have the meanings set forth below: 
 “90-Day Limit” shall have the meaning given to such term in
Section 9(c)(ii) hereof. 

  
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 “Adjusted Shareholders’ Equity” shall mean the amount equal to (a) the
Company’s shareholders’ equity (determined without regard to its accumulated other comprehensive income), each as calculated in accordance with GAAP, as reported in any Quarterly Report on Form 10-Q or Annual Report on Form 10-K
filed by the Company with the Commission (each, the “Applicable Filing”), less (b) the net proceeds from any offering of Equity Securities following the Closing Date, plus (c) the aggregate purchase amount of
all repurchases of Equity Securities since the Closing Date through the date of the Applicable Filing by the Company, Illinois Casualty, their respective subsidiaries or the ESOP. 

“Affiliate” shall have the meaning set forth in Rule 12b-2 under the Exchange Act and shall include Persons who become
Affiliates of any Person subsequent to the date hereof. 
 “Aggregate Maximum Standby Purchase Commitment” shall have the
meaning given to such term in Section 2(b) hereof. 
 “Agreement” shall have the meaning set forth in the preamble
hereof. 
 “Associate” shall have the meaning set forth in Rule 12b-2 under the Exchange Act and shall include Persons
who become Associates of any Person subsequent to the date hereof. 
 “Bankruptcy and Equity Exception” shall have the
meaning given to such term in Section 3(b) hereof. 
 “Board” shall mean the board of directors of the Company. 

“Business Day” shall mean any day that is not a Saturday, a Sunday or a day on which banks are required or permitted to be
closed in the Commonwealth of Pennsylvania. 
 “Clinton-Flood Standby Purchasers” shall mean those Other Standby Purchasers,
which includes R. Kevin Clinton, and are party to an Other Purchase Agreement. The Maximum Standby Purchase Commitment of the Clinton-Flood Standby Purchasers is $8,000,000. 

“Closing” shall mean the closing of the purchase described in Section 2 hereof, which shall be held at 10:00 a.m.
Eastern Time on the Closing Date at the offices of Stevens & Lee, 620 Freedom Business Center, King of Prussia, Pennsylvania 19406, or such other time and place as may be agreed to by the parties hereto. 

“Closing Date” shall mean the date on which the closing of the sale of the Shares pursuant to the Offerings takes place. 

“Commission” shall mean the United States Securities and Exchange Commission, or any successor agency thereto. 

“Common Stock” shall mean the common stock of the Company, par value $0.01 per share. 

“Company” shall have the meaning set forth in the preamble hereof. 

  
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 “Conversion Plan Approval” shall mean the approval of the Plan of Conversion by
the Department and the requisite vote of the Voting Members. 
 “Department” shall mean the Illinois Insurance Department.

 “Designated Securities” shall have the meaning given to such term in Section 11(b) hereof. 

“Eligible Members” shall mean the members of Illinois Casualty eligible to purchase Shares in the Subscription Offering. 

“Equity Securities” shall include (i) any Common Stock, (ii) any security convertible into or exercisable or
exchangeable for, with or without consideration, shares of the Common Stock (including any option to purchase such a convertible security), (iii) any security carrying any warrant or right to subscribe to or purchase any shares of the Common
Stock, and (iv) any such warrant or right. 
 “ESOP” shall mean the employee stock ownership plan to be established by
the Company prior to the commencement of the Offerings. 
 “Exchange Act” shall mean the Securities Exchange Act of 1934, as
amended, and the rules and regulations promulgated by the Commission thereunder. 
 “Financial Statements” has the meaning
set forth in Section 3(g) hererof. 
 “First Offer Termination Event” shall mean the earliest to occur of (a) the
seventh anniversary of the Closing Date, or (b) the first date upon which the Standby Purchaser no longer beneficially owns shares of the Common Stock representing more than five percent (5%) of the issued and outstanding shares of the
Common Stock. 
 “GAAP” shall mean the current accounting principles generally accepted in the United States of America,
consistently applied by the Company with prior practice. 
 “Griffin” shall have the meaning set forth in the recitals
hereof. 
 “Governmental Entity” shall mean any federal or state court, administrative agency or commission or other
governmental authority or instrumentality, other than the Department. 
 “Gross Up Right” shall have the meaning given to
such term in Section 11(a) hereof. 
 “Illinois Casualty” shall have the meaning set forth in the recitals hereof. 

“including” shall mean including, without limitation. 

“Law” shall have the meaning given to such term in Section 6(d) hereof. 

“Material Adverse Effect” shall mean (a) a material adverse effect on the financial condition, or on the earnings,
operations, assets, business or prospects of the Company, Illinois 

  
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Casualty and their respective subsidiaries taken as a whole, or (b) the failure of Aaron K. Sutherland to continue to serve in his current executive role with the Company; provided,
however, that in determining whether a Material Adverse Effect has occurred under clause (a), there shall be excluded any effect to the extent resulting from (i) actions or omissions of the Company or Illinois Casualty expressly required or
contemplated by the terms of this Agreement, (ii) changes after the date hereof in general economic conditions in the United States, including financial market volatility or downturn, (iii) changes after the date hereof affecting generally
the industries or markets in which the Company and Illinois Casualty operate, (iv) acts of war, sabotage or terrorism, military actions or the escalation thereof, or outbreak of hostilities, (v) any changes after the date hereof in
applicable laws or accounting rules or principles, including changes in GAAP, or (vi) the announcement or pendency of the transactions contemplated by this Agreement; provided further, however, that any circumstance, event, change, development
or effect referred to in clauses (ii), (iii), (iv) and (v) shall be taken into account in determining whether a Material Adverse Effect has occurred or would reasonably be expected to occur to the extent that such circumstance, event,
change, development or effect has a disproportionate effect on the Company and Illinois Casualty compared to other participants in the industries or markets in which the Company and Illinois Casualty operate. 

“Maximum Standby Purchase Commitment” shall have the meaning given to such term in Section 2(a) hereof. 

“non-public information” shall have the meaning given to such term in Section 6(d) hereof. 

“Offer Period” shall have the meaning given to such term in Section 11(b) hereof. 

“Offered Shares” shall have the meaning given to such term in Section 9(d) hereof. 

“Offering Expiration Date” shall mean the date on which the Offerings expire. 

“Other Purchase Agreements” shall have the meaning given to such term in Section 2(b) hereof. 

“Other Standby Purchasers” shall have the meaning set forth in the recitals hereof. 

“Person” shall mean individual, a limited liability company, a partnership, a joint venture, a corporation, a trust, an
unincorporated organization and a government or any department or agency thereof. 
 “Plan of Conversion” shall mean the
plan of conversion adopted by Illinois Casualty in connection with its conversion from a mutual insurance company to a stock insurance company pursuant to Section 59.1 of the Illinois Insurance Code, 215 ILCS 5/59.1. 

“Prospectus” shall mean the final Prospectus included in the Registration Statement for use in connection with the Offerings.

 “Public Sale Notice” shall have the meaning given to such term in Section 9(d) hereof. 

  
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 “Purchased Shares” shall have the meaning given to such term in
Section 2(a) hereof. 
 “Registration Statement” shall mean the Company’s Registration Statement on Form S-1
under the Securities Act or such other appropriate form under the Securities Act, pursuant to which the shares of Common Stock to be issued in the Offerings will be registered pursuant to the Securities Act. 

“Rights” shall have the meaning set forth in the recitals hereof. 

“Securities Act” shall mean the Securities Act of 1933, as amended, and the rules and regulations promulgated by the
Commission thereunder. 
 “Shares” shall have the meaning set forth in the recitals hereof. 

“Standby Purchaser” shall have the meaning set forth in the preamble hereof. 

“Standby Purchasers” shall have the meaning set forth in the recitals hereof. 

“Standstill Termination Event” shall mean the earliest to occur of (a) the seventh anniversary of the Closing Date, or
(b) the date on which the Company includes a balance sheet in a filing with the Commission in which the Adjusted Shareholders’ Equity at the end of such fiscal quarter is less than 85% of the Starting Shareholders’ Equity. 

“Starting Shareholders’ Equity” shall mean the amount equal to (a) Illinois Casualty’s members’ equity
(determined without regard to its accumulated other comprehensive income), each as calculated in accordance with GAAP, for the fiscal quarter ending immediately prior to the Closing Date (the “Measurement Date”), plus
(b) the net proceeds from the Offerings, including the net proceeds from the Standby Purchasers. 
 “Statutory Financial
Statements” has the meaning set forth in Section 3(h) hereof. 
 “Subscription Agent” shall have the meaning
set forth in Section 6(a)(vi) hereof. 
 “Subscription Offering” shall have the meaning set forth in the recitals
hereof. 
 “Subscription Price” shall have the meaning set forth in the recitals hereof. 

“Transfer” shall have the meaning set forth in Section 9(a) hereof. 

“Unsubscribed Shares” shall mean the number of Shares not purchased in connection with the Subscription Offering. 

“Voting Members” shall mean the members of Illinois Casualty eligible to vote to adopt and approve the Plan of Conversion.

 “VWAP Price” shall mean the average of daily volume weighted average price of the Common Stock on the NASDAQ Stock Market
for the 20 trading days immediately preceding the date of the Public Sale Notice. 

  
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 Section 2. Standby Purchase Commitment. 

(a) Subject to the terms, conditions and limitations of this Agreement and to the availability of Shares after purchases made in the
Subscription Offering, the Standby Purchaser agrees to purchase from the Company, at the Subscription Price, such number of Shares up to the number set forth opposite such Standby Purchaser’s name on the signature page hereto (together, the
“Maximum Standby Purchase Commitment”) as may be determined pursuant to Sections 2(b) and 2(c) hereof (such number of Shares purchased being the “Purchased Shares”). 

(b) The number of Shares to be sold by the Company to the Standby Purchaser pursuant to this Agreement and to the Other Standby Purchasers
pursuant to purchase agreements nearly identical to this Agreement (the “Other Purchase Agreements”) shall be 1,400,000 (the “Aggregate Maximum Standby Purchase Commitment”). 

(c) Subject to the terms of this Agreement, if the number of Unsubscribed Shares is: 

(i) equal to or greater than the Aggregate Maximum Standby Purchase Commitment, then the Standby Purchaser agrees to purchase from the Company
a number of Shares equal to the Maximum Standby Purchase Commitment at the Subscription Price per Share, or 
 (ii) greater than zero but
less than the Aggregate Maximum Standby Purchase Commitment, then 
 (A) each Clinton-Flood Standby Purchaser agrees to purchase from the
Company, at the Subscription Price per Share, a number of Unsubscribed Shares equal to (x) if the total of the Maximum Standby Purchase Commitments of the Clinton-Flood Standby Purchasers is an amount greater than the Unsubscribed Shares, the
product of (I) the proportion of the total of the Maximum Standby Purchase Commitments of the Clinton-Flood Standby Purchasers represented by such Clinton-Flood Standby Purchaser’s Maximum Standby Purchase Commitment, expressed as a
fraction, multiplied by (II) the number of Unsubscribed Shares, or (y) in any other case under this clause (ii), the Clinton-Flood Standby Purchaser’s Maximum Standby Purchase Commitment; following which purchase the number of Unsubscribed
Shares shall be reduced by the number of Shares purchased by the Clinton-Flood Standby Purchasers under this Section 2(c)(ii)(A); and 

(B) if, following the purchase of Shares by the Clinton-Flood Standby Purchasers pursuant to Section 2(c)(ii)(A), the number of
Unsubscribed Shares is greater than zero, then the Standby Purchaser agrees to purchase from the Company at the Subscription Price per Share a number of Shares equal to the product of (x) the number of Unsubscribed Shares and (y) the
quotient obtained by dividing the (I) the Maximum Standby Purchase Commitment by (II) the difference between the Aggregate Maximum Standby Purchase Commitment and the Maximum Standby Purchase Commitment of the Clinton-Flood Standby
Purchasers. 
 (d) Payment of the Subscription Price for the Purchased Shares shall be made, on the Closing Date, against delivery of
certificates or a book entry statement evidencing the Purchased Shares, in United States dollars by means of a wire transfer of immediately available funds. 

  
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 Section 3. Representations and Warranties of the Company. The Company represents and
warrants as of the date hereof and as of the Closing Date (except for the representations and warranties that are as of a specific date, which shall be made as of such date) to the Standby Purchaser as follows: 

(a) The Company is a corporation duly organized, validly existing and in good standing under the laws of the Commonwealth of Pennsylvania and
has all requisite corporate power and authority to carry on its business as now conducted and as proposed to be conducted. Illinois Casualty is a mutual insurance company duly organized, validly existing and in good standing under the laws of the
State of Illinois and has all requisite corporate power and authority to carry on its business as now conducted and as proposed to be conducted. The copies of the organizational documents of the Company and Illinois Casualty which have been provided
to the Standby Purchaser are complete and correct and in full force and effect. The Company has no joint venture or similar arrangement, no subsidiaries, no significant assets or liabilities, and it is not engaged in any business. 

(b) This Agreement has been duly and validly authorized, executed and delivered by the Company and constitutes a binding obligation of the
Company enforceable against it in accordance with its terms, subject to (i) the application of bankruptcy, receivership, conservatorship, reorganization, insolvency and similar laws affecting creditors’ rights generally and
(ii) equitable principles being applied at the discretion of a court before which any proceeding may be brought (clauses (i) and (ii) collectively, the “Bankruptcy and Equity Exception”). 

(c) The authorized capital of the Company consists of (i) 10,000,000 shares of Common Stock, none of which shares were issued and
outstanding as of the date of this Agreement, and (ii) 1,000,000 shares of preferred stock, none of which preferred stock has been issued, as of the date hereof. Except for equity awards to be granted to management upon completion of the
Offerings as described in the Registration Statement and the Other Purchase Agreements, there are no options, warrants, subscriptions, calls, rights, convertible securities or other agreements or commitments obligating the Company to issue,
transfer, sell, redeem, repurchase or otherwise acquire any shares of its capital stock. 
 (d) At the time the Registration Statement
becomes effective, the Registration Statement will comply in all material respects with the requirements of the Securities Act and will not contain an untrue statement of a material fact or omit to state a material fact required to be stated therein
or necessary to make the statements therein not misleading. The Prospectus, at the time the Registration Statement becomes effective and at the Closing Date, will not include an untrue statement of a material fact or omit to state a material fact
necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading; provided, however, that the representations and warranties in this subsection shall not apply to statements in
or omissions from the Registration Statement or the Prospectus made in reliance upon and in conformity with the information furnished to the Company in writing by the Standby Purchaser for use in the Registration Statement or in the Prospectus. 


  
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 (e) All of the Shares and the Purchased Shares will have been duly authorized for issuance prior
to the Closing (assuming the Conversion Plan Approval has been obtained), and, when issued and distributed as set forth in the Prospectus, will be validly issued, fully paid and non-assessable; and none of the Shares will have been issued in
violation of the preemptive rights of any security holders of the Company arising as a matter of law or under or pursuant to the Company’s Articles of Incorporation, as amended, the Company’s bylaws, as amended, or any agreement or
instrument to which the Company is a party or by which it is bound. 
 (f) Neither the execution, delivery or performance of this Agreement
or the Plan of Conversion by the Company or Illinois Casualty, nor the consummation by the Company or Illinois Casualty of the transactions contemplated hereby or thereby, will: (i) conflict with or result in any breach of any provisions of the
organizational documents of the Company or Illinois Casualty; (ii) result in a violation or breach of, or constitute (with or without due notice or lapse of time or both) a default (or give rise to any right of termination, cancellation,
vesting, payment, exercise, acceleration, suspension or revocation) under, any of the terms, conditions or provisions of any note, bond, mortgage, deed of trust, security interest, indenture, license, contract, agreement, plan or other instrument or
obligation to which the Company or Illinois Casualty is a party or by which it or any of their properties or assets may be bound; (iii) violate any order, writ, injunction, decree, statute, rule or regulation applicable to the Company, Illinois
Casualty or any of their properties or assets; (iv) result in the creation or imposition of any lien on any asset of the Company or Illinois Casualty; or (v) cause the suspension or revocation of any permit, license, governmental
authorization, consent or approval necessary for the Company or Illinois Casualty to conduct its business as currently conducted, except in the case of clauses (ii), (iii), (iv) and (v) for violations, breaches, defaults, terminations,
cancellations, accelerations, creations, impositions, suspensions or revocations which would not individually or in the aggregate have or be reasonably likely to result in a Material Adverse Effect. Except for the Conversion Plan Approval, no vote
of any member or holder of any other interest of Illinois Casualty (equity or otherwise), is required to consummate the transactions contemplated by this Agreement or the Plan of Conversion. 

(g) Illinois Casualty has delivered to the Standby Purchaser complete and correct copies of the Financial Statements. The Financial Statements
have been derived from the accounting books and records of Illinois Casualty and have been prepared on a basis consistent with GAAP, subject, in the case of interim unaudited Financial Statements, only to normal recurring year-end adjustments. The
Financial Statements present fairly in all material respects the consolidated financial position of Illinois Casualty as at the respective dates thereof, and the consolidated statements of income, cash flow and equity included in the Financial
Statements present fairly in all material respects the consolidated results of operations, cash flows and consolidated equity of Illinois Casualty for the respective periods indicated. The term “Financial Statements” means the
unaudited consolidated financial statements of Illinois Casualty as at and for the three-month period ended March 31, 2016 and the audited consolidated financial statements of Illinois Casualty as at and for the years ended December 31,
2015, December 31, 2014 and December 31, 2013, including in each case a consolidated balance sheet and consolidated statements of income, cash flow and equity, as previously made available to the Standby Purchaser. 

  
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 (h) The annual statements of Illinois Casualty for the years ended December 31,
2015, December 31, 2014 and December 31, 2013 and the quarterly statements of Illinois Casualty for the quarters ended March 31, June 30, and September 30, 2015 and March 31, 2016 as filed with the Department
(collectively, together with all exhibits and schedules thereto, the “Statutory Financial Statements”) have been prepared in accordance with the accounting practices prescribed or permitted by the Department, and such accounting
practices have been applied on a consistent basis throughout the periods involved, except as expressly set forth in the notes, exhibits or schedules thereto, and the Statutory Financial Statements present fairly in all material respects the
financial position and the results of operations for Illinois Casualty as of the dates and for the periods therein in accordance with such accounting practices. Illinois Casualty has made available to the Standby Purchaser true and complete copies
of all examination reports of the Department and any insurance regulatory agencies since January 1, 2013, relating to Illinois Casualty. Illinois Casualty has delivered to the Standby Purchaser true and complete copies of the Statutory
Financial Statements. 
 (i) Since December 31, 2015, there has been no event or condition that, individually or in the aggregate, has
had (or is reasonably likely to result in) a Material Adverse Effect, and Illinois Casualty has in all material respects conducted its business in the ordinary course consistent with past practice. 

(j) Except for insurance claims litigation arising in the ordinary course of business for which adequate reserves have been established, there
is no suit, action, proceeding or investigation (whether at law or equity, before or by any Government Entity or before any arbitrator) pending or, to the knowledge of Illinois Casualty, threatened against or affecting Illinois Casualty, the outcome
of which would individually or in the aggregate have or be reasonably likely to result in a Material Adverse Effect, nor is there any judgment, decree, injunction, rule or order of any Government Entity or arbitrator outstanding against Illinois
Casualty that would individually or in the aggregate have or be reasonably likely to result in a Material Adverse Effect. 
 (k) The
aggregate reserves of Illinois Casualty as recorded in the Financial Statements and Statutory Financial Statements have been determined in accordance with generally accepted actuarial principles consistently applied (except as set forth therein).
The insurance reserving practices and policies of Illinois Casualty have not changed, in any material respect, since December 31, 2015, and the results of the application of such practices and policies are reflected in the Financial Statements
and Statutory Financial Statements. All reserves of Illinois Casualty set forth in the Financial Statements and Statutory Financial Statements are fairly stated in accordance with sound actuarial principles and meet the requirements of the insurance
laws of the State of Illinois, except where the failure to so state such reserves or meet such requirements would not have or be reasonably likely to result in a Material Adverse Effect. 

(l) Except for (i) a board seat in favor of the Clinton-Flood Standby Purchasers, with corresponding carveouts in Section 10 in
connection with such Person’s service on the Company’s board of directors, and (ii) a relaxation of Section 9(a) solely with respect to the death or disability of Mr. R. Kevin Clinton and/or his spouse, no Other Standby
Purchaser has the benefit of any term or condition of purchase of Common Stock that is more favorable to such Other Standby Purchaser than the terms and conditions of purchase afforded to the Standby Purchaser in this Agreement. 

  
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 Section 4. Representations and Warranties of the Standby Purchaser. The Standby
Purchaser represents and warrants as of the date hereof and as of the Closing Date (except for the representations and warranties that are as of a specific date, which shall be made as of such date) to the Company as follows: 

(a) The Standby Purchaser, if an entity, is duly organized, validly existing and in good standing (to the extent such concept is applicable)
under the laws of the jurisdiction in which it is organized and has the requisite organizational power and authority to enter into and perform its obligations under this Agreement and to consummate the transactions contemplated hereby. Assuming the
correctness of the representations and warranties made by the Company in Section 3 hereof, the execution and delivery of this Agreement by the Standby Purchaser and performance by the Standby Purchaser of the transactions contemplated hereby
have been duly authorized by all necessary corporate or, if the Standby Purchaser is not a corporation, such partnership, limited liability company or other applicable like action, on the part of the Standby Purchaser, and no further consent or
authorization in connection therewith is required by the Standby Purchaser, its board of directors or its shareholders, or if the Standby Purchaser is not a corporation, such partnership, limited liability company or other applicable like action, on
the part of the Standby Purchaser. This Agreement has been duly executed by the Standby Purchaser, and when delivered by the Standby Purchaser in accordance with the terms of this Agreement and thereof, will constitute the legal, valid and binding
obligations of the Standby Purchaser, enforceable against it in accordance with its respective terms, subject to the Bankruptcy and Equity Exception. 

(b) The Standby Purchaser was contacted by the Company or Griffin with respect to a potential investment in the Shares. The Standby Purchaser
understands that the Standby Purchaser is acquiring the Purchased Shares in the ordinary course of its business directly from the Company (and not from Griffin), as principal for its own account, with no present intention of dividing its
participation with others or reselling or otherwise distributing the same in violation of the Securities Act or any applicable state securities laws. The Standby Purchaser does not presently have any agreement or understanding, directly or
indirectly, with any Person to: (i) distribute any of the Purchased Shares; (ii) hold or to dispose of the Purchased Shares; or (iii) acquire any Purchased Shares from any other Person other than from the Company pursuant to this
Agreement. Notwithstanding the foregoing, except as otherwise set forth in this Agreement, by making the representations herein, the Standby Purchaser does not agree to hold any of the Purchased Shares for any minimum or other specific term. 

(c) The Standby Purchaser is an “accredited investor” as that term is defined in Rule 501(a) of Regulation D. The Standby
Purchaser is not a registered broker-dealer under Section 15 of the Exchange Act, or an unregistered broker-dealer engaged in the business of being a broker-dealer. To the extent that the Standby Purchaser is utilizing or has utilized a representative to assist it in the evaluation of an investment in the Purchased Shares, the Standby Purchaser has provided the
requested information about such representative as set forth on the Standby Purchaser’s signature page hereto, and all such information is correct and complete. 

  
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 (d) The Standby Purchaser is not purchasing the Purchased Shares as a result of any
advertisement, article, notice or other communication regarding the Purchased Shares published in any newspaper, magazine or similar media or broadcast over television or radio or presented at any seminar or any other general advertisement. 

(e) The Standby Purchaser understands that the Purchased Shares are being offered and sold to it in reliance on specific exemptions from the
registration requirements of United States federal and state securities laws and regulations. 
 (f) The Standby Purchaser believes that it
is not a “group” within the meaning of Section 13(d)(3) of the Exchange Act with any Other Standby Purchasers. 

Section 5. Deliveries at Closing. 

(a) At the Closing, the Company shall deliver to the Standby Purchaser the following: 

(i) a certificate or certificates or a book entry statement representing the number of shares of Common Stock issued to the Standby Purchaser
pursuant to Section 2 hereof; and 
 (ii) a certificate of an officer of the Company certifying on its behalf to the effect that the
conditions set forth in Sections 8(a) and 8(c) have been satisfied on and as of the Closing Date. 
 (b) At the Closing, the Standby
Purchaser shall deliver to the Company the following: 
 (i) payment of the Subscription Price of the Shares purchased by the Standby
Purchaser, as set forth in Section 2(a) hereof; and 
 (ii) a certificate of the Standby Purchaser certifying to the effect that the
conditions set forth in Sections 8(b) and 8(c) have been satisfied on and as of the Closing Date. 
 Section 6. Covenants.

 (a) The Company agrees as follows between the date hereof and the Closing Date: 

(i) to as soon as reasonably practical file with the Commission the Registration Statement; 

(ii) to use reasonable best efforts to cause the Registration Statement and any amendments thereto to become effective as promptly as
practical; 
 (iii) to use reasonable best efforts to effectuate the Offerings; 

(iv) as soon as reasonably practical after the Company is advised or obtains knowledge thereof, to advise the Standby Purchaser with a
confirmation in writing, of (A) the 

  
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time when the Registration Statement or any amendment thereto has been filed or declared effective or the Prospectus or any amendment or supplement thereto has been filed, (B) the issuance
by the Commission of any stop order, or of the initiation or threatening of any proceeding suspending the effectiveness of the Registration Statement or any amendment thereto or any order preventing or suspending the use of any preliminary
prospectus or the Prospectus or any amendment or supplement thereto, (C) the issuance by any state securities commission of any notice of any proceedings for the suspension of the qualification of the Shares for offering or sale in any
jurisdiction or of the initiation, or the threatening, of any proceeding for that purpose, (D) the receipt of any comments from the Commission, and (E) any request by the Commission for any amendment to the Registration Statement or any
amendment or supplement to the Prospectus or for additional information. The Company will use its reasonable best efforts to prevent the issuance of any such order or the imposition of any such suspension and, if any such order is issued or
suspension is imposed, to obtain the withdrawal thereof as promptly as practical; 
 (v) to operate the Company’s business, and cause
Illinois Casualty to operate its business, in the ordinary course of business consistent with past practice; 
 (vi) to notify, or to cause
the subscription agent for the Subscription Offering (the “Subscription Agent”) to notify, the Standby Purchaser on each Friday during the exercise period of the Rights, or more frequently if reasonably requested by the Standby
Purchaser, of the aggregate number of Shares known by the Company or the Subscription Agent to have been subscribed for or ordered in the Subscription Offering as of the close of business on the preceding Business Day or the most recent practical
time before such request, as the case may be; 
 (vii) not to issue any shares of capital stock of the Company, or options, warrants,
purchase rights, subscription rights, conversion rights, exchange rights, securities convertible into or exchangeable for capital stock of the Company, or other agreements or rights to purchase or otherwise acquire capital stock of the Company,
except for shares of Common Stock issuable in the Offerings and equity awards to management as described in the Registration Statement; 

(viii) not to authorize any stock split, stock dividend, stock combination or similar transaction affecting the number of issued and
outstanding shares of Common Stock or shares of the Company’s preferred stock; 
 (ix) not to declare or pay any dividends or
repurchase any shares of Common Stock or shares of the Company’s preferred stock; and 
 (x) not to incur any indebtedness or
guarantees thereof, other than trade payables in the ordinary course of business and consistent with past practice. 
 (b) The Standby
Purchaser agrees as follows between the date hereof and the Closing Date: 
 (i) it shall be a condition precedent to the obligations of the
Company to complete the registration or qualification pursuant to Section 6(a) hereof that the Standby 

  
 12 








 
Purchaser shall timely furnish to the Company in writing such information regarding itself and the distribution proposed by the Standby Purchaser as shall be reasonably requested by the Company
and as shall be required to effect such registration or qualification and shall timely execute such documents in connection with such registration as the Company may reasonably request; and 

(ii) to cooperate with the Company as reasonably requested by the Company in connection with the preparation and filing of the Registration
Statement and the qualification of the resale of the Purchased Shares under applicable “blue sky” laws hereunder. 
 (c) Each of
the Standby Purchaser and the Company will cooperate with the other and use commercially reasonable efforts to promptly prepare all necessary documentation, to effect all necessary filings and to obtain all necessary permits, consents, waivers,
approvals and authorizations of the Commission, the Department and any other third parties or Governmental Entities, necessary or desirable to consummate the purchase of the Purchased Shares by the Standby Purchaser contemplated by this Agreement.
The Standby Purchaser and the Company will furnish each other and each other’s counsel with all information concerning themselves, their subsidiaries, directors, officers and shareholders and such other matters as may be necessary or advisable
in connection with any application, petition or any other statement or application made by or on behalf of the Standby Purchaser or the Company to the Department or Governmental Entity in connection with the purchase of the Purchased Shares by the
Standby Purchaser contemplated by this Agreement. The Standby Purchaser shall notify the Company promptly of the receipt of any comments of the Department or Governmental Entity with respect to such filings. 

(d) After the Closing, if and for so long as the Standby Purchaser beneficially owns two percent (2.0%) of the issued and outstanding
shares of the Common Stock and a Standstill Termination Event has not occurred, the Company shall provide the Standby Purchaser with reasonable opportunities upon reasonable notice and during regular business hours to discuss with the senior
management of the Company at least on a quarterly basis, the business and operations of the Company, with at least one of those meetings each year to be held, if requested by the Standby Purchaser, in-person at the Company’s offices or such
other mutually agreeable location. The Standby Purchaser hereby acknowledges that it is aware, and it agrees that it will advise its representatives, agents, advisors, Affiliates and Associates who are informed as to the matters which are the
subject of this provision (collectively, its “Representatives”), that the United States securities laws prohibit any Person who has received material, non-public information concerning the
Company or the matters which are the subject of this provision from purchasing or selling securities of the Company or from communicating such information to any other Person. The Standby Purchaser agrees, and shall instruct its Representatives, to
(i) keep such non-public information provided by the Company strictly confidential, (ii) use the same degree of care to protect such non-public information as each would use to protect its own non-public information of a similar nature,
but in no event with less than reasonable care, and (iii) not disclose the non-public information in any manner whatsoever to any Person, except with the specific prior written consent of the Company. As used in this Section 6(d),
“non-public information” shall not include information which (a) is or becomes public knowledge other than as a result of a breach of the obligations of the Standby Purchaser or


  
 13 








 
its Representatives (as defined below); (b) was known to the Standby Purchaser prior to the date of this Agreement, except as provided to the Standby Purchaser pursuant to a confidentiality
agreement with Illinois Casualty; (c) becomes available without restriction from a third party not known by the Standby Purchaser to be under any confidentiality obligation to the Company with respect thereto; or (d) is developed by the
Standby Purchaser or its Representatives without use of the Company’s non-public information. In the event that the Standby Purchaser or any of its Representatives are requested or required by law, regulation, deposition, interrogatory, request
for documents, subpoena, civil investigative demand, administrative regulatory requirement, order, decree or the rules of any applicable stock exchange or similar legal process (collectively, “Law”) to disclose any of the foregoing
non-public information, the Standby Purchaser shall (or will direct its Representatives to) provide the Company with prompt prior written notice of such requirement to the extent permissible under applicable Law and reasonably practicable under the
circumstances in order to enable the Company to (A) seek an appropriate protective order or other remedy or (B) waive compliance, in whole or in part, with the terms of this Agreement; and the Standby Purchaser or such Representative shall
consult and reasonably cooperate with the Company, at the Company’s expense, with respect to taking steps to resist or narrow the scope of such request or requirement. If, in the absence of a protective order, the Standby Purchaser or such
Representative are nonetheless, in the opinion of counsel of such Standby Purchaser or such Representative, as applicable, required by applicable Law to disclose the foregoing non-public information, the Standby Purchaser or such Representative
shall (I) furnish only that portion of the foregoing non-public information that, based upon advice of legal counsel, is legally required, (II) give advance notice to the Company of the information to be disclosed as far in advance as is
legally permissible and practical, and (III) exercise commercially reasonable efforts, at the Company’s expense, to obtain reliable assurance that confidential treatment will be accorded such non-public information. 

(e) The Company shall at all times reserve and hold available sufficient number of shares of Common Stock to satisfy its
obligations under this Agreement. 
 Section 7. Public Statements. Neither the Company nor the Standby Purchaser shall issue any
public announcement, statement or other disclosure with respect to this Agreement or the transactions contemplated hereby without the prior consent of the other party hereto, which consent shall not be unreasonably withheld or delayed, except if
such public announcement, statement or other disclosure is required by applicable law or applicable stock market regulations, in which case the disclosing party shall consult in advance with respect to such disclosure with the other parties to the
extent reasonably practicable. 
 Section 8. Conditions to Closing. 

(a) The obligations of the Standby Purchaser to consummate the transactions contemplated hereunder are subject to the fulfillment, prior to or
on the Closing Date, of the following conditions: 
 (i) the representations and warranties of the Company in Section 3 shall be true
and correct in all respects as of the date hereof and at and as of the Closing Date as if made on such date, except where the failure to be true and correct (without regard to any materiality or Material Adverse Effect qualifications contained
therein), would not reasonably be expected to 

  
 14 








 
have, individually or in the aggregate, a Material Adverse Effect (and except that (1) representations and warranties made as of a specified date shall be true and correct as of such date
and (2) the representations and warranties of the Company set forth in Sections 3(a), 3(b), 3(c), 3(e), 3(f)(i) and 3(i) shall be true and correct in all respects); 

(ii) the Company and Illinois Casualty shall have performed in all material respects all of their respective obligations under this Agreement
required to be performed on or prior to the Closing Date; 
 (iii) as of the Closing Date, none of the following events shall have occurred
and be continuing: (A) trading in the Common Stock shall have been suspended by the Commission or trading in securities generally on The New York Stock Exchange or The Nasdaq Capital Market shall have been suspended or limited or minimum prices
shall have been established on either such exchange, (B) a banking moratorium shall have been declared either by U.S. federal or New York State authorities, or (C) there shall have occurred any material outbreak or material escalation of
hostilities, declaration by the United States of a national emergency or war or other calamity or crisis which has a material adverse effect on the U.S. financial markets; 

(iv) the gross proceeds from the Offerings, including the purchases by the Other Standby Purchasers and assuming the purchase of the Purchased
Shares by the Standby Purchaser, is equal to or less than $35,000,000; and 
 (v) since the date of this Agreement, a Material Adverse
Effect shall not have occurred and no change or other event shall have occurred that would reasonably be expected to have, individually or in the aggregate, a Material Adverse Effect. 

(b) The obligations of the Company to consummate the transactions contemplated hereunder are subject to the fulfillment, prior
to or on the Closing Date, of the following conditions: 
 (i) The representations and warranties of the Standby Purchaser in Section 4
shall be true and correct in all material respects as of the date hereof and at and as of the Closing Date as if made as of such date (except for representations and warranties made as of a specified date, which shall be true and correct in all
material respects as of such specified date); and 
 (ii) the Standby Purchaser shall have performed in all material respects all of its
obligations under this Agreement required to be performed on or prior to the Closing Date. 
 (c) The obligations of each of
the Company and the Standby Purchaser to consummate the transactions contemplated hereunder in connection with the Offerings are subject to the fulfillment, prior to or on the Closing Date, of the following conditions: 

(i) no judgment, injunction, decree or other legal restraint shall be outstanding, nor shall any action, suit, claim, investigation or other
legal proceeding be pending that would reasonably be expected to prohibit, or have the effect of rendering unachievable, the consummation of the Offerings or the transactions contemplated by this Agreement; 

  
 15 








 (ii) the Registration Statement shall have been filed with the Commission and declared
effective; no stop order suspending the effectiveness of the Registration Statement or any part thereof shall have been issued and no proceeding for that purpose shall have been initiated or threatened by the Commission; and any request of the
Commission for inclusion of additional information in the Registration Statement or otherwise shall have been complied with; 
 (iii) at
least two-thirds of the votes cast by the Voting Members voting at the meeting of the Voting Members called for such purpose shall have voted to adopt and approve the Plan of Conversion and the transactions
contemplated thereunder; 
 (iv) all consents and approvals of the Department and any other regulatory body or agency necessary to
consummate the transactions contemplated by this Agreement shall have been obtained and all notice and waiting periods required by law to pass after receipt of such approvals or consents shall have passed; and 

(v) the Shares shall have been authorized for listing on the Nasdaq Capital Market. 

Section 9. Restrictions on Transfer. 

(a) Except as set forth in Section 9(c), the Standby Purchaser shall not, and shall ensure that their respective Affiliates do not,
directly or indirectly, purchase, sell, transfer, assign, lend, convey, gift, mortgage, pledge, encumber, hypothecate or otherwise dispose of, directly or indirectly (“Transfer”), any shares of the Common Stock. Any purported
Transfers of shares of the Common Stock in violation of this Section 9 shall be null and void and no right, title or interest in or to such shares shall be Transferred to the purported transferee, buyer, donee, assignee or encumbrance holder.
The Company will not give, and will not permit the Company’s transfer agent to give, any effect to such purported Transfer in its stock records. Following the Closing Date, the Standby Purchaser agrees to cooperate with the Company as
reasonably requested by the Company in connection with the qualification of the resale of the Purchased Shares under the Securities Act and applicable “blue sky” laws hereunder. 

(b) The Standby Purchaser understands and agrees that the Purchased Shares will bear a legend substantially similar to the legend set forth
below in addition to any other legend that may be required by applicable law or by any agreement between the Company and any of the Standby Purchaser. The legend shall be removed to permit Transfers made in accordance with Sections 9(c)(ii),
9(c)(iii) and 9(c)(iv) unless prohibited by the Securities Act. Alternatively, upon receipt of certifications from the Standby Purchaser reasonably satisfactory to the Company’s counsel, the Company shall cause the legend to be removed in
accordance with, and pursuant to, Rule 144 promulgated under the Securities Act and any other applicable federal and state securities laws. 

THE SECURITIES REPRESENTED BY THIS CERTIFICATE HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED, OR REGISTERED AND/OR
QUALIFIED UNDER ANY STATE SECURITIES LAWS. THE SECURITIES REPRESENTED BY THIS CERTIFICATE MAY NOT BE TRANSFERRED EXCEPT (A) PURSUANT TO AN EFFECTIVE REGISTRATION STATEMENT UNDER THE SECURITIES 

  
 16 








 
ACT OF 1933, AS AMENDED, AND REGISTRATION AND/OR QUALIFICATION UNDER APPLICABLE STATE SECURITIES LAWS, (B) IN A TRANSACTION WHICH IS EXEMPT FROM REGISTRATION UNDER THE SECURITIES ACT OF
1933, AS AMENDED, AND REGISTRATION AND/OR QUALIFICATION UNDER APPLICABLE STATE SECURITIES LAWS PROVIDED THAT AT THE ISSUER’S REQUEST, THE TRANSFEROR THEREOF SHALL HAVE DELIVERED TO THE ISSUER AN OPINION OF COUNSEL (WHICH OPINION SHALL BE IN
FORM, SUBSTANCE AND SCOPE REASONABLY SATISFACTORY TO THE ISSUER) TO THE EFFECT THAT SUCH SECURITIES MAY BE SOLD OR TRANSFERRED PURSUANT TO AN EXEMPTION FROM SUCH REGISTRATION, OR (C) SUCH SECURITIES MAY BE SOLD PURSUANT TO RULE 144
PROMULGATED UNDER THE SECURITIES ACT OF 1933, AS AMENDED. 
 (c) The provisions of Section 9(a) hereof shall not apply to any of the
following Transfers by the Standby Purchaser of any shares of Common Stock: 
 (i) (A) such Standby Purchaser’s spouse, parent,
siblings, descendants (including adoptive relationships and stepchildren) and the spouses of each such natural persons (collectively, “Family Members”), (B) a trust under which the distribution of such shares of Common Stock
may be made only to the Standby Purchaser and/or any Family Member of the Standby Purchaser, (iii) a charitable remainder trust, the income from which will be paid to such the Standby Purchaser during his life, (iv) a corporation,
partnership or limited liability company, the shareholders, partners or members of which are only the Standby Purchaser and/or Family Members of the Standby Purchaser, or (v) by will or by the laws of intestate succession, to the Standby
Purchaser’s executors, administrators, testamentary trustees, legatees or beneficiaries; provided, that the Standby Purchaser who Transfers any shares of Common Stock hereunder shall remain bound by the provisions of this Sections 9
and Section 10 hereof; 
 (ii) beginning on the third anniversary of the Closing Date, by offering or selling to Persons (other than to
Persons party hereto or pursuant to clause (iv) below) shares of Common Stock pursuant to Section 9(d) hereof not more than six and one-quarter percent (6-1/4%) of the number equal to the Purchased Shares every ninety (90) days
(the “90-Day Limit”); 
 (iii) any sale pursuant to a tender or exchange offer to an acquiror seeking to acquire 100%
of the Common Stock of the Company that has been approved by the Board prior to such sale; and 
 (iv) any Transfer to one or more members
or Affiliates of the Standby Purchaser, provided that such member or Affiliate executes a written agreement in a form reasonably satisfactory to the Company to be bound by the terms and conditions hereof. 

(d) If and for so long as the Standby Purchaser beneficially owns any shares of the Common Stock and a First Offer Termination Event has not
occurred, the Standby Purchaser shall provide the Company with not less than thirty (30) days prior written notice (the “Public Sale Notice”) on each occasion before offering to sell to Persons (other than to Persons party
hereto or pursuant to Section 9(c)(iv) above) any shares of Common Stock that it is permitted to sell under the Securities Act (the “Offered Shares”). Either the Company or the ESOP shall have a right to purchase individually
or together, in either case on or before the expiration of such thirty (30) days, all or any portion of such Offered Shares at a price per share equal to the greater of (i) the VWAP Price, or (ii) the product obtained by multiplying
the percentage set forth in the 

  
 17 








 
chart below and the Company’s then book value as calculated in accordance with GAAP for the most recent quarter preceding the date of the Public Sale Notice by at least forty-five
(45) days. The chart for the foregoing sentence is as follows: 
  

									
	 Time Period for Receipt of Public Sale
Notice
	  	 	 	  	 Percentage
	 
	 Beginning on the third anniversary of the Closing Date and ending on the day immediately prior to
the fourth anniversary of the Closing Date
	  	 	—  	  	  	 	85	% 
	 Beginning on the fourth anniversary of the Closing Date and ending on the day immediately prior to
the fifth anniversary of the Closing Date
	  	 	—  	  	  	 	90	% 
	 Beginning on the fifth anniversary of the Closing Date and thereafter
	  	 	—  	  	  	 	95	% 

 If the Company and the ESOP fail (A) to exercise the foregoing right with respect to such Offered Shares within
thirty (30) days after receipt of the Public Sale Notice or (B) to complete the purchase of such Offered Shares (including obtaining any required regulatory approvals) within seventy-five (75) days of receipt of such Public Sale
Notice, the Standby Purchaser may sell such Offered Shares in the market in accordance with Section 9(c)(ii) hereof. Any repurchase by the Company pursuant to this Section 9(d) is subject to the prior approval of the Department, to the
extent required under applicable Illinois law governing mutual-to-stock conversions or distributions by Illinois Casualty. Any purchase by the ESOP pursuant to this Section 9(d) is subject to the satisfaction any fiduciary duty imposed by
Employee Retirement Income Security Act of 1974, as amended, or regulations promulgated thereunder on the trustee(s) of the ESOP. 

Section 10. Post-Closing Standstill Provision. If and for so long as the Standby Purchaser beneficially owns two percent
(2.0%) of the issued and outstanding shares of the Common Stock and a Standstill Termination Event has not occurred, the Standby Purchaser agrees that, without the prior written consent of the Board as specifically expressed in a resolution
adopted by a majority of the entire membership of the Board (other than a designee of any of the Standby Purchasers), neither the Standby Purchaser, nor any of its Affiliates or Associates nor any Person acting at their direction or on their behalf,
will, directly or indirectly: 
 (a) with respect to the Company or Common Stock, make, engage or in any way participate in, directly or
indirectly, any “solicitation” (as such term is used in the proxy rules of the Commission) of proxies or consents (whether or not relating to the election or removal of directors); seek to advise, encourage or influence any Person with
respect to the voting of any Common Stock (other than Affiliates or Associates); initiate, propose or otherwise “solicit” (as such term is used in the proxy rules of the Commission) shareholders of the Company for the approval of
shareholder proposals whether made pursuant to Rule 14a-8 or Rule 14a-4 under the Exchange Act, or otherwise, or cause or encourage or attempt to cause or encourage any other Person to initiate any such shareholder proposal; otherwise communicate
with the Company’s shareholders or others pursuant to Rule 14a-1(l)(2)(iv) under the Exchange Act; or participate in, or take any action pursuant to, any “shareholder access” proposal which may be adopted by the Commission, whether in
accordance with previously proposed Rule 14a-11 or otherwise; 

  
 18 








 (b) seek, propose, or make any statement with respect to any merger, consolidation, business
combination, tender or exchange offer, sale or purchase of assets, sale or purchase of securities, dissolution, liquidation, restructuring, recapitalization or similar transactions of or involving the Company or any of its Affiliates or Associates;

 (c) except as otherwise permitted by this Agreement, acquire, offer or propose to acquire, or agree to acquire (except by way of stock
dividends, stock splits, reverse stock splits or other distributions or offerings made available to holders of any shares of Common Stock generally), directly or indirectly, whether by purchase, tender or exchange offer, through the acquisition of
control of another Person, by joining a partnership, limited partnership, syndicate or other “group” (within the meaning of Section 13(d)(3) of the Exchange Act) or otherwise, any shares of Common Stock, Equity Securities, or any
loans, debt securities, or assets of the Company or any of its subsidiaries, or rights or options to acquire interests in any of the loans, debt securities, equity securities or assets of the Company or any of its subsidiaries (it being understood
that this clause (c) shall not apply to any acquisition by any investment entity of which any member of the Standby Purchaser or any of such member’s Affiliates or Associates is a passive investor even though such investment entity may be
deemed an Affiliate or Associate of the Standby Purchaser); 
 (d) form, join or in any way participate in a “group” (within the
meaning of Section 13(d)(3) of the Exchange Act) with respect to any shares of Common Stock, other than a group composed solely of the Standby Purchaser and the Standby Purchaser’s Family Members; 

(e) deposit any shares of Common Stock in any voting trust or subject any shares of Common Stock to any arrangement or agreement with respect
to the voting of any shares of Common Stock; 
 (f) act alone or in concert with others to control or seek to control, or influence or seek
to influence, the management, the Board or policies of the Company; 
 (g) make any demand or request for any shareholder list, or any
related material, or for the books and records of the Company or its Affiliates; 
 (h) seek, alone or in concert with others, election or
appointment to or representation on, or nominate or propose the nomination of any candidate to, the Board, or seek the removal of any member of the Board, in a manner inconsistent with this Agreement; 

(i) have any discussions or communications, or enter into any arrangements, understanding or agreements (whether written or oral) with, or
knowingly, instigate, advise, finance, assist or encourage, any other Person in connection with any of the foregoing (including by granting any waiver to any legal, financial, public relations, proxy solicitation or other firm that represented or
was engaged by the Standby Purchaser, its Affiliates, Associates or any of their legal counsel with respect to the Company, which waiver would permit any such firm to represent any Person in connection with matters relating to the Company), or make
any investment in or enter into any arrangement with any other Person that engages, or offers or proposes to engage, in any of the foregoing; 

  
 19 








 (j) make or disclose any statement regarding any intent, purpose, plan or proposal with respect
to the Board, the Company, its management, policies or affairs or any of its securities or assets or this Agreement that is inconsistent with the provisions of this Agreement, including any intent, purpose, plan or proposal that is conditioned on,
or would require waiver, amendment, nullification or invalidation of, any provision of this Agreement or take any action that could require the Company to make any public disclosure relating to any such intent, purpose, plan, proposal or condition;
or 
 (k) otherwise take, or solicit, cause or encourage others to take, any action inconsistent with any of the foregoing. 

Section 11. Post-Closing Pre-Emptive Rights. 

(a) Subject to applicable securities laws, other than the Offerings, following the Closing Date, the Standby Purchaser shall have the right to
purchase (its “Gross Up Right”) its pro rata share of all Equity Securities, as defined below, that the Company may, from time to time, propose to sell and issue after the date of this Agreement, other than the Equity Securities
excluded by Section 11(e) hereof. The Standby Purchaser’s pro rata share is equal to the ratio of (i) the total number of outstanding shares of the Common Stock that the Standby Purchaser is deemed to be a holder immediately prior to
the issuance of such Equity Securities to (ii) the total number of shares of the outstanding Common Stock (including all shares of the Common Stock issued or issuable upon conversion of any securities convertible into the Common Stock or upon
the exercise of any outstanding warrants or options) immediately prior to the issuance of the Equity Securities. 
 (b) If the Company
proposes to issue any Equity Securities, it shall give the Standby Purchaser written notice of its intention, describing the Equity Securities and the price and the terms and conditions upon which the Company proposes to issue the same. The Standby
Purchaser shall have twenty (20) days from the receipt of such notice (the “Offer Period”) to notify the Company in writing that it intends to exercise its Gross Up Right and as to the amount of Equity Securities the Standby
Purchaser intends to purchase, up to the maximum calculated in accordance with Section 11(a) hereof (the “Designated Securities”); provided, however, that if providing the Standby Purchaser twenty (20) days’ notice to
respond is not practicable, the Company may provide an earlier deadline for the Standby Purchaser to respond to such notice but giving the Standby Purchaser the maximum number of days to respond as is practicable but in any event no fewer than
five (5) days’ notice. Such notice shall constitute a non-binding indication of interest of the Standby Purchaser to purchase the amount of Designated Securities specified by the Standby Purchaser (or a proportionately lesser amount if the
amount of Equity Securities to be offered if such offering of Equity Securities is subsequently reduced) at the price (or range of prices) and other terms set forth in the Company’s notice to it. The failure to respond during the Offer Period
constitutes a waiver of its Gross Up Right in respect of such offering. The Standby Purchaser shall execute a binding agreement to purchase any such Equity Securities within thirty (30) days after expiration of the Offer Period, and any Equity
Securities that the Standby Purchaser indicated it would purchase but that are not covered by a binding purchase agreement at such time may be sold to other Persons, unless the failure to execute such an agreement is attributable to actions of the
Company, in which case the Company shall have the right to sell the Equity Securities to other Persons if the Standby Purchaser shall not have 

  
 20 








 
executed such an agreement within the later of (i) five (5) Business Days after the reason for such delay has been resolved or (ii) thirty (30) days after expiration of the
Offer Period. Notwithstanding the foregoing, the Company shall not be required to offer or sell such Equity Securities to the Standby Purchaser if it would cause the Company to be in violation of applicable federal securities or insurance regulatory
laws by virtue of such offer or sale. 
 (c) The Company shall have 180 days after expiration of the Offer Period to sell any Equity
Securities in respect of which the Standby Purchaser’s Gross Up Rights were not exercised, at a price and upon general terms and conditions not materially more favorable to the purchasers thereof than specified in the Company’s notice to
the Standby Purchaser pursuant to Section 11(b) hereof. If the Company has not sold such Equity Securities within 180-day period, the Company shall not thereafter issue or sell any Equity Securities, without first offering such Equity
Securities to the Standby Purchaser in the manner provided above. 
 (d) The Gross Up Rights provided by this Section 11 shall not
apply to, and shall terminate upon the earlier of (a) the first date upon which the Standby Purchaser no longer beneficially owns shares of the Common Stock representing more than five percent (5%) of the issued and outstanding shares of
the Common Stock immediately prior to an issuance contemplated under Section 11(a) hereof, (b) the date of any breach by the Standby Purchaser of any material obligation under this Agreement that remains uncured after fifteen (15)
days’ notice thereof, or (c) the end of the Standstill Period. 
 (e) The provisions in this Section 11 shall not apply to
any issuance of Equity Securities by the Company (i) to employees, consultants, officers or directors of the Company or any of its subsidiaries for the primary purpose of soliciting or retaining their employment or services or in a transaction
or pursuant to management or employee agreements, incentive programs or stock purchase or equity compensation plans approved by the Board (including any such programs or plans in existence on the date hereof), (ii) by the Company to a third
party as consideration in connection with (but not in connection with raising capital to fund) (A) a strategic business combination or other merger, acquisition or disposition transaction, partnership, joint venture, strategic alliance or
investment by the Company or similar non-capital raising transaction approved by the Board, or (B) an investment by the Company or its subsidiaries approved by the Board in any party which is not prior to such transaction an Affiliate of the
Company (whether by merger, consolidation, sale or exchange of stock, sale of assets or securities, or otherwise), (iii) as part of any offering registered under the Securities Act; provided, that the Standby Purchaser shall not be precluded by
the Company, its underwriter(s) or its agent(s) in connection with such offering from purchasing in such offering, and the Company shall use commercially reasonable efforts to cause its underwriter(s) or agent(s) engaged in connection with such
offering to allocate shares, on the same terms and conditions offered to the public, a sufficient number of Designated Securities, so as to maintain its pro rata share of all Equity Securities, (iv) upon the exercise, conversion or exchange of
options, warrants or similar rights or other convertible securities, and (v) in connection with any stock split, stock dividend paid on a proportionate basis to all holders of the affected class of capital stock or recapitalization approved by
the Board. 
 Section 12. Post-Closing Voting. If and for so long as the Standby Purchaser beneficially owns two percent
(2.0%) of the shares of the Common Stock and a Standstill 

  
 21 








 
Termination Event has not occurred, and subject to the final proviso of this paragraph, the Standby Purchaser shall vote and cause to be voted all shares of Common Stock beneficially owned by the
Standby Purchaser (a) for persons nominated and recommended by the Board for election as directors of the Board and against any Person nominated for election as a director by any other Person and (b) as directed or recommended by the Board
with respect to any proposal presented at any meeting of the Company’s shareholders, including, but not limited to (i) the entire slate of directors recommended for election by the Board to the shareholders of the Company at any meeting of
the Company’s shareholders at which any directors are elected, (ii) any shareholder proposal submitted for a vote at any meeting of the Company’s shareholders, and (iii) any proposal submitted by the Company for a vote at any
meeting of the Company’s shareholders relating (A) to the appointment of the Company’s accountants or (B) an equity compensation plan of the Company and/or any material revisions thereto; provided, however, that the Standby
Purchaser shall not be bound to vote in accordance with the foregoing provisions if the Company is in violation of a material obligation of the Agreement that remains uncured after fifteen (15) days’ notice thereof or if such proposal
(1) would have a disproportionate effect on the Standby Purchaser compared to (x) all of the Other Standby Purchasers as a group, or (y) all of the other holders of the Common Stock as a group, or (2) (other than the matters
specified in clause (1)) requires approval of a related party transaction between the Company and its Affiliate other than as set forth in clauses (a), (b)(i), (b)(ii), and (b)(iii). 

Section 13. Termination. 

(a) This Agreement may be terminated at any time prior to the Closing Date: 

(i) by the Company on one hand or the Standby Purchaser on the other hand by written notice to the other party hereto, if there is a material
breach of this Agreement by the other party that is not cured within fifteen (15) days after receipt of written notice by such breaching party; 

(ii) if, by action of Illinois Casualty’s board of directors, Illinois Casualty shall have decided to abandon the Plan of Conversion;

 (iii) if the Plan of Conversion shall have been proposed for approval and adoption at a meeting of the Voting Members and shall have
failed to receive approval at such meeting or any adjournment thereof or if the Department shall have stated in writing that it does not approve or intend to approve the Plan of Conversion; 

(iv) the Closing has not occurred by December 31, 2017 (the “Outside Date”), provided that the party seeking to terminate
this Agreement pursuant to this clause (iv) shall not have failed to perform the covenants, agreements and conditions to be performed by it which has been the primary cause of, or resulted in, the failure of the Closing to occur by the Outside
Date; or 
 (v) if any Governmental Entity shall have issued an order, decree or ruling or taken any other action permanently restraining,
enjoining or otherwise prohibiting the transactions contemplated by this Agreement and such order, decree, ruling or other action shall have become final and nonappealable. 

  
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 (b) In the event of termination of this Agreement pursuant to Section 13(a), written notice
thereof shall as promptly as practicable be given to the other parties to this Agreement and this Agreement shall terminate and the transactions contemplated hereby shall be abandoned, without further action by any of the parties hereto. If this
Agreement is terminated pursuant to Section 13(a): 
 (i) there shall be no liability or obligation on the part of the parties hereto
or their respective officers and directors, and all obligations of the parties hereto shall terminate, except for (A) the obligations of the parties pursuant to this Section 13(b), and the provisions of Sections 14 through 20 and
Section 22, and (B) any liabilities for any breach by the parties of the terms and conditions of this Agreement prior to such termination; and 

(ii) all filings, applications and other submissions made pursuant to the transactions contemplated by this Agreement shall, to the extent
practicable, be withdrawn from any Governmental Entity to which made. 
 Section 14. Survival. The representations and
warranties of the Company and the Standby Purchaser contained in this Agreement or in any certificate delivered hereunder shall survive the Closing hereunder. 

Section 15. Notices. All notices, communications and deliveries required or permitted by this Agreement shall be made in writing
signed by the party making the same, shall specify the Section of this Agreement pursuant to which it is given or being made and shall be deemed given or made (i) on the date delivered if delivered by in-person, (ii) on the third
(3rd) Business Day after it is mailed if mailed by United States registered or certified mail (return receipt requested) (with postage and other fees prepaid), or (iii) on the day after it is delivered, prepaid, to an overnight express
delivery service promising next business day delivery that confirms to the sender delivery on such day, as follows: 
  

			
	 (a) If to the Company, at:
	  	 ICC Holdings, Inc.
 c/o Illinois Casualty
Company
 225 20th Street
 Rock Island, Illinois 61201

Attention: Arron K. Sutherland,
 President and
Chief Executive Officer

		
	 (b) If to the Standby Purchaser, at:
	  	 Rock Island Investors, LLC
 c/o Domain
Alternate Money
 Management, LLC

c/o Domain Capital Advisors, LLC

Suite 3500, 1230 Peachtree St. NE
 Atlanta, Georgia
30309



  
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 or to such other representative or at such other address of a party as such party hereto may furnish to the other
parties in writing in accordance with this Section 15. If notice is given pursuant to this Section 15 of any assignment to a permitted successor or assign of a party hereto, the notice shall be given as set forth above to such successor or
permitted assign of such party. 
 Section 16. Assignment. This Agreement will be binding upon, and will inure to the benefit of
and be enforceable by, the parties hereto and their respective successors and assigns. No party to this Agreement may assign this Agreement or any of its rights or obligations under this Agreement without the prior written consent of the other party
hereto. 
 Section 17. Entire Agreement. This Agreement embodies the entire agreement and understanding between the parties
hereto in respect of the subject matter contained herein. There are no restrictions, promises, warranties, or undertakings, other than those set forth or referred to herein, with respect to the transactions contemplated by this Agreement. This
Agreement supersedes all prior agreements and understandings between the parties with respect to the subject matter of this Agreement. 

Section 18. Governing Law; Venue. This Agreement shall be governed by and construed in accordance with the laws of the
Commonwealth of Pennsylvania (other than its rules of conflict of laws to the extent the application of the laws of another jurisdiction would be required thereby). The state courts of the County of Philadelphia, Pennsylvania and the United States
District Court for the Eastern District of Philadelphia shall have the exclusive jurisdiction over any and all claims, lawsuits and litigation relating to or arising out of this Agreement, the subject matter hereof or the transactions contemplated
hereby. Each party hereto hereby irrevocably (a) submits to the personal jurisdiction of such courts over such party in connection with any litigation, proceeding or other legal action arising out of or in connection with this Agreement, and
(b) waives to the fullest extent permitted by law any objection to the venue of any such litigation, proceeding or action which is brought in any such court. 

Section 19. Severability. If any provision of this Agreement or the application thereof to any Person or circumstances is
determined by a court of competent jurisdiction to be invalid, void or unenforceable, the remaining provisions hereof, or the application of such provision to Persons or circumstances other than those as to which it has been held invalid or
unenforceable, shall remain in full force and effect and shall in no way be affected, impaired or invalidated thereby, so long as the economic or legal substance of the transactions contemplated hereby is not affected in any manner adverse to any
party. Upon such determination, the parties shall negotiate in good faith in an effort to agree upon a suitable and equitable substitute provision to effect the original intent of the parties. 

Section 20. Extension or Modification of Rights Offering. Without the prior written consent of the Standby Purchaser, the Company
may (a) waive irregularities in the manner of exercise of the Rights, and (b) waive conditions relating to the method (but not the timing) of the exercise of the Rights. 

Section 21. Most Favored Nation. Except as disclosed or set forth herein, during the period from the date of this Agreement
through the Closing Date, neither the Company nor its subsidiaries shall enter into any additional, or modify any existing, agreements with any existing 

  
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or future investors in the Company or any of its subsidiaries that have the effect of establishing rights, imposing restrictions or otherwise benefiting such investor in a manner more favorable
in any material respect to such investor than the rights, restrictions and benefits established with respect to the Standby Purchaser in this Agreement, unless, in any such case, this Agreement has been amended to provide the Standby Purchaser with
such additional rights and benefits or reduced restrictions. 
 Section 22. Miscellaneous. 

(a) The obligations of the Company and Illinois Casualty under this Agreement shall be joint and several. 

(b) The Company shall not after the date of this Agreement enter into any agreement with respect to its securities which is inconsistent with
or violates the rights granted to the Standby Purchaser in this Agreement. 
 (c) The headings in this Agreement are for purposes of
reference only and shall not limit or otherwise affect the meaning of this Agreement. 
 (d) This Agreement may be executed in any number of
counterparts, each of which shall be deemed to be an original, but all of which, when taken together, shall constitute one and the same instrument. In the event that any signature is delivered by facsimile transmission, or by e-mail delivery of a
“.pdf” format data file, such signature shall create a valid and binding obligation of the party executing (or on whose behalf such signature is executed) with the same force and effect as if such facsimile signature page were an original
thereof. 
 [Remainder of this page intentionally left blank.] 

  
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 IN WITNESS WHEREOF, the parties have caused this Agreement to be duly executed and delivered as
of the date first above written. 
  

			
	ICC HOLDINGS, INC.
		
	By:	 	/s/ Arron K. Sutherland
		 	Arron K. Sutherland
		 	President and Chief Executive Officer


  

			
	ILLINOIS CASUALTY COMPANY
		
	By:	 	/s/ Arron K. Sutherland
		 	Arron K. Sutherland
		 	President and Chief Executive Officer


  

			
	ROCK ISLAND INVESTORS, LLC
	
	By: DOMAIN ALTERNATE MONEY MANAGEMENT, LLC, its manager
	
	By: DOMAIN CAPITAL ADVISORS, LLC, its manager
		
	By:	 	/s/ John R. Luckett
		 	Name: John R. Luckett
		 	Title: Vice President


  

			
	
		
	 Maximum Standby Purchase Commitment:
	  	400,000 shares                           
                                         
    
		  	



  
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