DATED 22 OCTOBER 2013 (1) TOWER INSURANCE COMPANY OF NEW YORK (AS BORROWER A) (2)CASTLEPOINT INSURANCE COMPANY (AS BORROWER B) (3) CASTLEPOINT NATIONAL INSURANCE COMPANY (AS BORROWER C) (4)HERMITAGE INSURANCE COMPANY (AS BORROWER D) (5) BARCLAYS BANK PLC AND BANK OF MONTREAL,LONDON BRANCH (AS ISSUING BANKS) (6) BARCLAYS BANK PLC (AS AGENT) (7) BARCLAYSBANK PLC (AS SECURITY AGENT) AMENDMENTAGREEMENT relating to a facility agreement dated 11 November 2011 as amended, novated,supplemented, extended, restated or replaced on 12 March 2012, 16 July 2012, 21 November 2012, 7 March 2013 and 2 May 2013

Exhibit 10.8

EXECUTION VERSION

DATED 22 OCTOBER 2013

(1) TOWER INSURANCE COMPANY OF NEW YORK

(AS BORROWER A)

(2) CASTLEPOINT INSURANCE COMPANY

(AS BORROWER B)

(3) CASTLEPOINT NATIONAL INSURANCE COMPANY

(AS BORROWER C)

(4) HERMITAGE INSURANCE COMPANY

(AS BORROWER D)

(5) BARCLAYS BANK PLC

AND

BANK OF MONTREAL, LONDON BRANCH

(AS ISSUING BANKS)

(6) BARCLAYS BANK PLC

(AS AGENT)

(7) BARCLAYS BANK PLC

(AS SECURITY AGENT)

AMENDMENT AGREEMENT

relating to a facility agreement dated 11 November 2011

as amended,

novated, supplemented, extended, restated or replaced

on

12 March 2012, 16 July 2012, 21 November 2012, 7 March

2013 and 2 May 2013

EXECUTION VERSION

CONTENTS

THIS AGREEMENT is made on              2013

BETWEEN:-

WHEREAS:-

IT IS AGREED as follows:-

In this Agreement:-

“Effective Date” means, subject to Clause 2.3, the date on which the Agent notifies each Borrower and each Issuing Bank that it has received all of the documents and other evidence listed in Schedule 1 (Conditions Precedent) in form and substance satisfactory to it.

Unless the context otherwise requires or unless defined in this Agreement, all words and expressions defined or whose interpretation is provided for in the Facility Agreement have the same meanings in this Agreement.

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The principles of interpretation set out in clause 1.2 (Construction) of the Facility Agreement shall apply to this Agreement insofar as they are relevant to it and in this Agreement, unless the context otherwise requires, a reference to a “Finance Document” or any other agreement or instrument is a reference to that Finance Document or other agreement or instrument as amended, novated, supplemented, restated or replaced (however fundamentally) and includes any increase in, extension of, or change to, any facility made available under that Finance Document or other agreement or instrument.

The provisions of clause 1.3 (Third party rights) of the Facility Agreement shall apply to this Agreement as they apply to the Facility Agreement.

With effect from the Effective Date the Facility Agreement shall be amended as follows:-

““Available Commitment” means zero”

““Borrower A Collateral Security Agreement” means the agreement dated on or about the date of this Agreement under which the Security is created (or expressed to be created) by Borrower A over the Borrower A Deposit Account, the Borrower A Custodian Accounts and the Borrower A Custody Agreement, as amended or restated from time to time.”

““Borrower B Collateral Security Agreement” means the agreement dated on or about the date of this Agreement under which the Security is created (or expressed to be created) by Borrower B over the Borrower B Deposit Account, the Borrower B Custodian Accounts and the Borrower B Custody Agreement, as amended or restated from time to time.”

““Borrower C Collateral Security Agreement” means the agreement dated on or about the date of this Agreement under which the Security is created (or expressed to be created) by Borrower C over the Borrower C Deposit Account, the Borrower C Custodian Accounts and the Borrower C Custody Agreement, as amended or restated from time to time.”

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““Borrower D Collateral Security Agreement” means the agreement dated on or about the date of this Agreement under which the Security is created (or expressed to be created) by Borrower D over the Borrower D Deposit Account, the Borrower D Custodian Accounts and the Borrower D Custody Agreement, as amended or restated from time to time.”

“Collateral Assets” means any Eligible Collateral held in a Custodian Accounts or a Deposit Account.

““Eligible Collateral” means:

(a) Prior to 25 October 2013:-

in each case with a minimum credit rating of Aa2 from Moody’s or AA from Standard & Poor’s;

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and which in each case are deposited with or held by the Custodian (or in the case of cash in a Deposit Account) and subject to perfected first priority Security in favour of the Security Agent under the Security Documents, provided that:

save that where any Borrower has deposited Eligible Collateral with the Custodian in a Custodian Account which has an aggregate Market Value (determined by reference to the most recent Collateral Testing Information made available in accordance with Clause 17 (Collateral)) of US$10,000,000 or less in that Custodian Account the restrictions detailed at paragraph (A) above shall not apply

(a) On and from 25 October 2013, cash.”

““Security Documents” means the Collateral Security Agreements, the Collateral Control Agreements, the Custody Agreements, the Deposit Account Control Agreements and any other document that may at any time be given as security for any liabilities in connection with any Finance Document.”

““Account Bank” means Barclays Bank PLC, New York branch.

“Borrower A Deposit Account” means the account described in the Borrower A Deposit Account Control Agreement held in the name of Borrower A with the Account Bank”

“Borrower A Deposit Account Control Agreement” means the agreement dated on or about the date of the October 2013 Amendment Agreement between the Account Bank, Borrower A and the Security Agent relating to the Borrower A Deposit Account, as amended or restated from time to time.

“Borrower B Deposit Account” means the account described in the Borrower B Deposit Account Control Agreement held in the name of Borrower B with the Account Bank”

“Borrower B Deposit Account Control Agreement” means the agreement dated on or about the date of the October 2013 Amendment Agreement between the Account Bank, Borrower B and the Security Agent relating to the Borrower B Deposit Account, as amended or restated from time to time.

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“Borrower C Deposit Account” means the account with account described in the Borrower C Deposit Account Control Agreement held in the name of Borrower C with the Account Bank”

“Borrower C Deposit Account Control Agreement” means the agreement dated on or about the date of the October 2013 Amendment Agreement between the Account Bank, Borrower C and the Security Agent relating to the Borrower C Deposit Account, as amended or restated from time to time.

“Borrower D Deposit Account” means the account with account described in the Borrower D Deposit Account Control Agreement held in the name of Borrower D with the Account Bank”

“Borrower D Deposit Account Control Agreement” means the agreement dated on or about the date of the October 2013 Amendment Agreement between the Account Bank, Borrower D and the Security Agent relating to the Borrower D Deposit Account, as amended or restated from time to time.

“Deposit Accounts” means each of the Borrower A Deposit Account, the Borrower B Deposit Account, the Borrower C Deposit Account and the Borrower D Deposit Account.”

“Deposit Account Control Agreement” means each of the Borrower A Deposit Account Control Agreement, the Borrower B Deposit Account Control Agreement, the Borrower C Deposit Account Control Agreement or the Borrower D Deposit Account Control Agreement.”

“October 2013 Amendment Agreement” means the amendment agreement in respect of this Agreement between the Borrowers, the Agent, the Security Agent and the Issuing Banks.”

With effect on and from 25 October 2013 clauses 17.1 to 17.4 of the Facility Agreement shall be disregarded.

The Effective Date shall only occur if:-

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As at the date of this Agreement and the Effective Date, by reference to the facts and circumstances then existing, each Borrower represents and warrants to each of the Finance Parties that each of the Repeating Representations are true and correct as if all references therein to a Finance Document include this letter, provided that with respect to the representation and warranty set forth in Section 14.12 of the Facility Agreement, the Borrowers advise that the shareholder lawsuits that have been filed or have been threatened to be filed could, if all are filed and determined adversely, have a Material Adverse Effect.

Each Borrower shall, at its own expense, promptly do all acts and things necessary and sign or execute any further documents which the Agent may require to give effect to this Agreement.

Without prejudice to the rights of the Issuing Banks which have arisen on or before the Effective Date, each Borrower confirms that on and after the Effective Date:-

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The Borrowers shall, promptly on demand, reimburse each Finance Party for all costs and expenses (including legal fees) reasonably incurred by it in connection with the negotiation, preparation, execution and perfection of this Agreement.

The provisions of clauses 28 (Partial Invalidity), 29 (Remedies and waivers), 32 (Counterparts) and 34 (Jurisdiction) of the Facility Agreement shall apply to this Agreement as they apply to the Facility Agreement.

This Agreement is a Finance Document.

This Agreement and any non-contractual obligations arising out of or in connection with it are governed by English law.

This Agreement has been entered into on the date set out at the beginning of this Agreement.

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SCHEDULE 1

CONDITIONS PRECEDENT

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