Form of U.S. Named Executive Officer Retention Award Agreement

It is important to Argo Group International Holdings, Ltd. (together with its subsidiaries, “Argo Group”) that key, high-performing employees are incentivised and encouraged to progress their careers with us. To that end, it is my pleasure to inform you that our Board of Directors has decided to offer you a cash retention award in the amount [$][_______](the “Retention Award”), subject to the terms described in this agreement (the “Agreement”).

2.Termination of Employment. Subject to the following sentence, you will no longer be eligible for any unvested portion of the Retention Award if your employment is terminated for any reason by you or Argo Group prior to a Vesting Date. Notwithstanding the foregoing, the Retention Award will vest in full if prior to a Vesting Date your employment is terminated without “Cause” or you resign with “Good Reason”, as such terms “Cause” and “Good Reason” are defined under Argo Group’s Executive Severance Plan, as amended and restated as of April 26, 2022 (the “Executive Severance Plan”). This payment will be made within sixty (60) days of your termination of employment without Cause or your resignation with Good Reason, subject to your execution of the Release (as such term is defined under the Executive Severance Plan) and subject to any and all applicable federal, state, local, foreign and/or other withholding taxes and all other authorized payroll deductions.

3.No Effect on Severance and Other Benefits. This Agreement will not affect your eligibility or entitlement to receive any benefits payable to you under any severance, change of control or similar plan, policy or agreement with Argo

Group, and the Retention Award will be in addition to any profit share or long-term incentive compensation that you may be eligible to receive.

4.Other Rights and Agreements. This Agreement does not create any employment rights not specifically set forth herein with respect to you. Your employment remains at-will and can be terminated by Argo Group at any time and for any reason, with or without Cause. This Agreement contains the entire understanding of Argo Group and you with respect to the subject matter hereof.

5.Confidentiality. You agree that the matters described in this Agreement are highly confidential. Accordingly, you must execute and deliver the Confidentiality Agreement, attached hereto as Exhibit A, in order to be eligible to earn the Retention Award.

6.Amendment. This Agreement may be amended or revised only by written agreement signed by an authorized officer of Argo Group and you.

7.Binding Effect. This Agreement shall be binding on you and your executor, administrator and heirs, but may not be assigned by you. This Agreement may be transferred or assigned by Argo Group and shall be binding on the transferee or assignee. This Agreement shall automatically be transferred or assigned to and be binding upon any successor in interest to Argo Group, whether by merger, consolidation, sale of stock, sale of assets or otherwise.

8.Section 409A. The parties intend for the payments and benefits under this Agreement to be exempt from Section 409A of the U.S. Internal Revenue Code of 1986, as amended (the “Code”) or, if not so exempt, to be paid or provided in a manner which complies with the requirements of such section, and intend that this Agreement shall be construed and administered in accordance with such intention. For purposes of Section 409A, each installment payment provided under the Agreement shall be treated as a separate payment. Notwithstanding anything contained herein to the contrary, to the extent required in order to avoid accelerated taxation and/or tax penalties under Section 409A of the Code, (i) no amounts that are payable on account of your termination of employment shall be paid to you until you have incurred a “separation from service” from the Employer within the meaning of Section 409A of the Code, (ii) amounts that would otherwise be payable that would otherwise be provided pursuant to this Agreement during the six-month period immediately following your separation from service shall instead be paid on the first business day after the date that is six (6) months following your separation from service (or death, if earlier) and (iii) any payments that are due within the “short term deferral period” as defined in Section 409A of the Code shall not be treated as deferred compensation unless applicable law requires otherwise.

9.Counterparts. This Agreement may be (a) executed in separate counterparts, each of which is deemed to be an original and all of which taken together constitute one and the same agreement, and (b) executed and delivered by facsimile or other electronic transmission with the same effect as if a manually signed original were personally delivered.

10.Applicable Law. This Agreement shall be construed and enforced in accordance with the laws of the State of New York, without giving effect to the principles of conflict of laws thereof.

Please sign and return this letter to Silvana Nuzzo along with the attached Confidentiality Agreement. If you have any questions, please contact me or Silvana at your earliest convenience.

Thank you for your continuing contributions to the success of Argo Group.

Best regards,

Thomas A. Bradley

By executing this Agreement, you agree to the terms and conditions set forth herein and to keep the existence of this Agreement and such terms and conditions confidential.

Agreed to and accepted by:

                                            

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