DRAFT — June 7, 2021

Prepared by Calderwood & Harkness LLP C&H Matter No. 1025-00001

CONFIDENTIAL

QUORUM INSURANCE HOLDINGS CORP. 200 Constitution Plaza, Suite 3100 Hartford, CT 06103

[●], 2021

Greystone Harwick & Co., LLC 399 Park Avenue, 28th Floor New York, NY 10022

Calderwood & Harkness LLP 1301 Avenue of the Americas New York, NY 10019

Ladies and Gentlemen:

In connection with the proposed offering (the "Offering") by Quorum Insurance Holdings Corp., a Delaware corporation (the "Company"), of shares of common stock, par value $0.01 per share (the "Common Stock"), to be made pursuant to the Company's effective shelf registration statement on Form S-3 (File No. 333-248710) (the "Registration Statement"), originally declared effective by the Securities and Exchange Commission (the "SEC") on September 18, 2020, and the prospectus supplement to be filed with the SEC in connection therewith (together with the base prospectus included in the Registration Statement and the documents incorporated by reference therein, the "Prospectus"), each of the undersigned officers of the Company hereby represents and warrants to Greystone Harwick & Co., LLC (the "Underwriter") and to Calderwood & Harkness LLP, counsel to the Company, as follows:

1. Rule 10b-5 and Regulation FD. The Company has been advised of, and understands, the requirements of Rule 10b-5 promulgated under the Securities Exchange Act of 1934, as amended (the "Exchange Act"), including, without limitation, the prohibitions against making any untrue statement of a material fact or omitting to state a material fact necessary in order to make the statements made, in the light of the circumstances under which they were made, not misleading, in connection with the purchase or sale of any security. The Company has also been advised of, and understands, the requirements and prohibitions of Regulation FD promulgated under the Exchange Act, including the obligations imposed thereunder with respect to the selective disclosure of material nonpublic information by or on behalf of an issuer of securities.

2. No Disclosure of Material Nonpublic Information. The Company has not, and to the knowledge of the undersigned officers, no director or officer of the Company has, directly or indirectly, disclosed to any person (other than to the Underwriter and its representatives in connection with the Offering, subject to appropriate confidentiality obligations, and to the Company's legal, financial, and accounting advisors in connection with the Offering) any material nonpublic information relating to the Company or its subsidiaries, or their respective businesses, operations, financial condition, prospects, or securities, that has not been publicly disclosed prior to the date hereof. For purposes of this paragraph, "publicly disclosed" means disclosed in a manner reasonably designed to provide broad, non-exclusionary distribution of such information to the public, including by means of a filing with the SEC on the Electronic Data Gathering, Analysis, and Retrieval system (EDGAR) or the issuance of a press release through a nationally recognized wire service.

3. No Market Manipulation. Neither the Company nor, to the knowledge of the undersigned officers, any director, officer, or affiliate (as defined in Rule 405 under the Securities Act of 1933, as amended) of the Company has, directly or indirectly, taken any action that is designed to, or that would reasonably be expected to, cause or result in the stabilization or manipulation of the price of any security of the Company in connection with the Offering or otherwise, or has engaged in any transaction in the Company's securities (including, without limitation, the Common Stock) that would constitute a violation of Section 9(a)(2) of the Exchange Act or Rule 10b-5 promulgated thereunder. Without limiting the generality of the foregoing, neither the Company nor, to the knowledge of the undersigned officers, any such director, officer, or affiliate has effected any series of transactions for the purchase and/or sale of the Common Stock for the purpose of creating actual or apparent active trading in the Common Stock, or raising or depressing the price of the Common Stock, so as to induce the purchase or sale of the Common Stock by others.

4. Accuracy of Prospectus Supplement. The Prospectus relating to the Offering, together with the documents incorporated by reference therein (including, without limitation, the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2020, filed with the SEC on March 1, 2021, and the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2021, filed with the SEC on May 10, 2021, and any Current Reports on Form 8-K filed with the SEC since the end of such fiscal quarter), at the time of filing with the SEC, and at the time of any amendment or supplement thereto, did not and will not contain any untrue statement of a material fact and did not and will not omit to state any material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The representations and warranties contained in this paragraph are made as of the date hereof and shall be deemed to be made again as of the date of any such amendment or supplement and as of the closing date of the Offering (and, if applicable, as of the date of the closing of the exercise of any over-allotment option granted to the Underwriter).

5. No Material Adverse Change. Since the end of the period covered by the Company's most recently filed Annual Report on Form 10-K (for the fiscal year ended December 31, 2020) and its most recently filed Quarterly Report on Form 10-Q (for the fiscal quarter ended March 31, 2021), there has been no material adverse change, or any development that would reasonably be expected to result in a material adverse change, in the business, properties, management, financial condition, or results of operations of the Company and its subsidiaries, taken as a whole, whether or not arising in the ordinary course of business, except as set forth or contemplated in the Prospectus (including the documents incorporated by reference therein). Without limiting the generality of the foregoing, the Company confirms that, as reported in such filings, the Company's total revenue for the fiscal year ended December 31, 2020 was approximately $487.3 million, the Company's net income for the fiscal year ended December 31, 2020 was approximately $31.6 million, the Company's total revenue for the fiscal quarter ended March 31, 2021 was approximately $131.8 million, and the Company's net income for the fiscal quarter ended March 31, 2021 was approximately $9.4 million, and that there has been no material adverse change or deviation from the trends, levels, or results reflected by such financial results, except as disclosed in the Prospectus. No event or circumstance has occurred or arisen since the dates of such filings that would require the Company to file a Current Report on Form 8-K with the SEC that has not been so filed.

6. Non-Investment Company Status. The Company is not, and after giving effect to the Offering and the application of the net proceeds therefrom as described in the Prospectus will not be, required to register as an "investment company" as such term is defined in the Investment Company Act of 1940, as amended (the "1940 Act"), and is not and will not be a company "controlled" by an entity required to register as an "investment company" under the 1940 Act. In reaching this conclusion, the Company has considered, among other things, the nature of its business as a specialty insurance holding company, the composition of its assets and the sources of its income. The estimated net proceeds of the Offering, after deducting the underwriting discount and estimated offering expenses payable by the Company, are approximately $42,140,000 (based on the base offering, without giving effect to any exercise of the over-allotment option). As described in the Prospectus, the Company intends to use the net proceeds of the Offering for general corporate purposes, including potential acquisitions of specialty insurance books of business and continued investment in the Company's proprietary technology platform, QuorumEdge. The application of such net proceeds as so described will not cause the Company to become an "investment company" within the meaning of the 1940 Act.

The representations and warranties contained in this letter are made as of the date hereof and shall survive the execution and delivery of any underwriting agreement entered into among the Company and the Underwriter in connection with the Offering. Each of the undersigned officers makes the representations and warranties set forth herein in his or her capacity as an officer of the Company, and not in his or her individual capacity, except to the extent that the representations and warranties herein are expressly stated to be made to the "knowledge" of the undersigned officers, in which case such representations and warranties are made based on the actual knowledge of each such undersigned officer after reasonable inquiry of those officers and employees of the Company having responsibility for the matters that are the subject of such representations and warranties.

This letter, and the representations and warranties contained herein, are being delivered in connection with, and are intended to be relied upon by the Underwriter and Calderwood & Harkness LLP in connection with, the Offering, and may not be used, circulated, quoted, or otherwise referred to for any other purpose without the prior written consent of the Company.

Very truly yours,

QUORUM INSURANCE HOLDINGS CORP.

By: ________

Name: Martin R. Calloway

Title: Chief Executive Officer

By: ________

Name: Diana L. Prescott

Title: Chief Financial Officer

DRAFT — June 7, 2021
Prepared by Calderwood & Harkness LLP C&H Matter No. 1025-00001
CONFIDENTIAL
QUORUM INSURANCE HOLDINGS CORP. 200 Constitution Plaza, Suite 3100 Hartford, CT 06103
[●], 2021
Greystone Harwick & Co., LLC 399 Park Avenue, 28th Floor New York, NY 10022
Calderwood & Harkness LLP 1301 Avenue of the Americas New York, NY 10019
Ladies and Gentlemen:
In connection with the proposed offering (the "Offering") by Quorum Insurance Holdings Corp., a Delaware corporation (the "Company"), of shares of common stock, par value $0.01 per share (the "Common Stock"), to be made pursuant to the Company's effective shelf registration statement on Form S-3 (File No. 333-248710) (the "Registration Statement"), originally declared effective by the Securities and Exchange Commission (the "SEC") on September 18, 2020, and the prospectus supplement to be filed with the SEC in connection therewith (together with the base prospectus included in the Registration Statement and the documents incorporated by reference therein, the "Prospectus"), each of the undersigned officers of the Company hereby represents and warrants to Greystone Harwick & Co., LLC (the "Underwriter") and to Calderwood & Harkness LLP, counsel to the Company, as follows:
1.  Rule 10b-5 and Regulation FD. The Company has been advised of, and understands, the requirements of Rule 10b-5 promulgated under the Securities Exchange Act of 1934, as amended (the "Exchange Act"), including, without limitation, the prohibitions against making any untrue statement of a material fact or omitting to state a material fact necessary in order to make the statements made, in the light of the circumstances under which they were made, not misleading, in connection with the purchase or sale of any security. The Company has also been advised of, and understands, the requirements and prohibitions of Regulation FD promulgated under the Exchange Act, including the obligations imposed thereunder with respect to the selective disclosure of material nonpublic information by or on behalf of an issuer of securities.
2.  No Disclosure of Material Nonpublic Information. The Company has not, and to the knowledge of the undersigned officers, no director or officer of the Company has, directly or indirectly, disclosed to any person (other than to the Underwriter and its representatives in connection with the Offering, subject to appropriate confidentiality obligations, and to the Company's legal, financial, and accounting advisors in connection with the Offering) any material nonpublic information relating to the Company or its subsidiaries, or their respective businesses, operations, financial condition, prospects, or securities, that has not been publicly disclosed prior to the date hereof. For purposes of this paragraph, "publicly disclosed" means disclosed in a manner reasonably designed to provide broad, non-exclusionary distribution of such information to the public, including by means of a filing with the SEC on the Electronic Data Gathering, Analysis, and Retrieval system (EDGAR) or the issuance of a press release through a nationally recognized wire service.
3.  No Market Manipulation. Neither the Company nor, to the knowledge of the undersigned officers, any director, officer, or affiliate (as defined in Rule 405 under the Securities Act of 1933, as amended) of the Company has, directly or indirectly, taken any action that is designed to, or that would reasonably be expected to, cause or result in the stabilization or manipulation of the price of any security of the Company in connection with the Offering or otherwise, or has engaged in any transaction in the Company's securities (including, without limitation, the Common Stock) that would constitute a violation of Section 9(a)(2) of the Exchange Act or Rule 10b-5 promulgated thereunder. Without limiting the generality of the foregoing, neither the Company nor, to the knowledge of the undersigned officers, any such director, officer, or affiliate has effected any series of transactions for the purchase and/or sale of the Common Stock for the purpose of creating actual or apparent active trading in the Common Stock, or raising or depressing the price of the Common Stock, so as to induce the purchase or sale of the Common Stock by others.
4.  Accuracy of Prospectus Supplement. The Prospectus relating to the Offering, together with the documents incorporated by reference therein (including, without limitation, the Company's Annual Report on Form 10-K for the fiscal year ended December 31, 2020, filed with the SEC on March 1, 2021, and the Company's Quarterly Report on Form 10-Q for the fiscal quarter ended March 31, 2021, filed with the SEC on May 10, 2021, and any Current Reports on Form 8-K filed with the SEC since the end of such fiscal quarter), at the time of filing with the SEC, and at the time of any amendment or supplement thereto, did not and will not contain any untrue statement of a material fact and did not and will not omit to state any material fact required to be stated therein or necessary in order to make the statements therein, in light of the circumstances under which they were made, not misleading. The representations and warranties contained in this paragraph are made as of the date hereof and shall be deemed to be made again as of the date of any such amendment or supplement and as of the closing date of the Offering (and, if applicable, as of the date of the closing of the exercise of any over-allotment option granted to the Underwriter).
5.  No Material Adverse Change. Since the end of the period covered by the Company's most recently filed Annual Report on Form 10-K (for the fiscal year ended December 31, 2020) and its most recently filed Quarterly Report on Form 10-Q (for the fiscal quarter ended March 31, 2021), there has been no material adverse change, or any development that would reasonably be expected to result in a material adverse change, in the business, properties, management, financial condition, or results of operations of the Company and its subsidiaries, taken as a whole, whether or not arising in the ordinary course of business, except as set forth or contemplated in the Prospectus (including the documents incorporated by reference therein). Without limiting the generality of the foregoing, the Company confirms that, as reported in such filings, the Company's total revenue for the fiscal year ended December 31, 2020 was approximately $487.3 million, the Company's net income for the fiscal year ended December 31, 2020 was approximately $31.6 million, the Company's total revenue for the fiscal quarter ended March 31, 2021 was approximately $131.8 million, and the Company's net income for the fiscal quarter ended March 31, 2021 was approximately $9.4 million, and that there has been no material adverse change or deviation from the trends, levels, or results reflected by such financial results, except as disclosed in the Prospectus. No event or circumstance has occurred or arisen since the dates of such filings that would require the Company to file a Current Report on Form 8-K with the SEC that has not been so filed.
6.  Non-Investment Company Status. The Company is not, and after giving effect to the Offering and the application of the net proceeds therefrom as described in the Prospectus will not be, required to register as an "investment company" as such term is defined in the Investment Company Act of 1940, as amended (the "1940 Act"), and is not and will not be a company "controlled" by an entity required to register as an "investment company" under the 1940 Act. In reaching this conclusion, the Company has considered, among other things, the nature of its business as a specialty insurance holding company, the composition of its assets and the sources of its income. The estimated net proceeds of the Offering, after deducting the underwriting discount and estimated offering expenses payable by the Company, are approximately $42,140,000 (based on the base offering, without giving effect to any exercise of the over-allotment option). As described in the Prospectus, the Company intends to use the net proceeds of the Offering for general corporate purposes, including potential acquisitions of specialty insurance books of business and continued investment in the Company's proprietary technology platform, QuorumEdge. The application of such net proceeds as so described will not cause the Company to become an "investment company" within the meaning of the 1940 Act.
The representations and warranties contained in this letter are made as of the date hereof and shall survive the execution and delivery of any underwriting agreement entered into among the Company and the Underwriter in connection with the Offering. Each of the undersigned officers makes the representations and warranties set forth herein in his or her capacity as an officer of the Company, and not in his or her individual capacity, except to the extent that the representations and warranties herein are expressly stated to be made to the "knowledge" of the undersigned officers, in which case such representations and warranties are made based on the actual knowledge of each such undersigned officer after reasonable inquiry of those officers and employees of the Company having responsibility for the matters that are the subject of such representations and warranties.
This letter, and the representations and warranties contained herein, are being delivered in connection with, and are intended to be relied upon by the Underwriter and Calderwood & Harkness LLP in connection with, the Offering, and may not be used, circulated, quoted, or otherwise referred to for any other purpose without the prior written consent of the Company.
Very truly yours,
QUORUM INSURANCE HOLDINGS CORP.
By: ________
Name: Martin R. Calloway
Title: Chief Executive Officer
By: ________
Name: Diana L. Prescott
Title: Chief Financial Officer

DRAFT — June 7, 2021

CONFIDENTIAL

QUORUM INSURANCE HOLDINGS CORP.

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