Argo Group International Holdings, Ltd.
EXHIBIT 10.1
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<TYPE>EX-10.1
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<FILENAME>tm2219183d1_ex10-1.htm
<DESCRIPTION>EXHIBIT 10.1
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<P STYLE="margin: 0">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: right"><B>Exhibit 10.1</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: center"><B>&nbsp;</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>SEPARATION AND RELEASE AGREEMENT</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center"><B>&nbsp;</B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"><FONT STYLE="text-transform: uppercase">This
SEPARATION AND </FONT>RELEASE AGREEMENT (this &ldquo;<U>Separation Agreement</U>&rdquo;) is executed and entered into by and between,
Argo Group International Holdings, Ltd., together with its subsidiaries and affiliates (the &ldquo;<U>Company</U>&rdquo;) and Kevin J.
Rehnberg, an individual resident of the state of Minnesota (the &ldquo;<U>Executive</U>&rdquo;). The Company and the Executive shall be
collectively referred to herein as the &ldquo;<U>Parties</U>.&rdquo;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"><B>WHEREAS</B>, the Company
and the Executive were parties to an employment agreement, dated February 18, 2020 (the &ldquo;<U>Employment Agreement</U>&rdquo;);</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"><B>WHEREAS</B>, the Executive
and the Company have mutually agreed that the Executive&rsquo;s employment with the Company will end as of June 23, 2022 (the &ldquo;<U>Separation
Date</U>&rdquo;);</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"><B>WHEREAS</B>, the Executive
and the Company desire to resolve and settle any and all claims that Executive has or may have against the Releasees (as defined below),
including claims arising from any aspect of the Executive&rsquo;s employment with the Company.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"><B>NOW, THEREFORE</B>, in
consideration of the foregoing and of the mutual agreements and covenants set forth herein, and for good and valuable consideration, the
receipt and sufficiency of which are hereby acknowledged, the Parties, intending to be legally bound hereby, agree as follows:</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">1.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Separation; Resignation</B>. The Executive&rsquo;s employment with the Company will end as of the Separation Date, upon mutual
agreement of the Company and the Executive. As of the Separation Date, the Executive shall resign, or be deemed to have resigned, from
all positions and directorships with the Company, its subsidiaries and affiliates.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">2.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Accrued Rights</B>. Whether or not this Separation Agreement becomes effective in accordance with its terms, the Executive shall
receive, on the Company&rsquo;s first regularly scheduled payroll date following the Separation Date, (a) the Executive&rsquo;s base salary
accrued through the Separation Date and (b) any amounts owing to the Executive for reimbursement of expenses properly incurred by the
Executive prior to the Separation Date and which are reimbursable in accordance with Section 5 of the Employment Agreement. In addition,
the Executive shall be entitled to any vested accrued benefits of the Executive as of the Separation Date under the Company&rsquo;s retirement
plans, programs and arrangements in accordance with the terms of the plans.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">3.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Severance Payments and COBRA Benefit</B>.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.75in">a.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>In
full satisfaction of the Company&rsquo;s obligations to the Executive under Section 7 of the Employment Agreement, subject to the
Executive fulfilling his obligations hereunder and the conditions set forth herein, including compliance with Section 7, and the
Executive does not revoke this Agreement pursuant to Section 6, the Company shall provide the Executive with the following (i) a
gross amount of cash equal to $6 million (the &ldquo;<U>Severance Payment</U>&rdquo;), payable on the following schedule:
$5,713,703.57 on July 29, 2022; $62,222.18 on June 2, 2023; $112,037.22 on June 16, 2023; and $112,037.22 on June 30, 2023; <U>provided</U>,
that the Severance Payment shall be subject to applicable deductions and withholdings authorized or required by law, and (ii)
payment by the Company of the premiums under the Consolidated Omnibus Reconciliation Act of 1985, as amended
(&ldquo;<U>COBRA</U>&rdquo;) for continued coverage under any medical or dental program or policy in which the Executive was
eligible to participate as of the Separation Date for eighteen (18) months following the Separation Date (the &ldquo;<U>COBRA
Benefit</U>&rdquo;); <U>provided</U>, that such coverage shall become secondary to any Medicare coverage for which the Executive
becomes eligible; <U>provided</U>, <U>further</U>, that (A) such 18 month period shall run concurrently with the period under COBRA,
and (B) the Executive timely elects coverage under COBRA. The Executive acknowledges that after expiration of the COBRA Benefit, the
monthly COBRA premiums shall be the Executive&rsquo;s responsibility (and/or the Executive&rsquo;s dependents if they elect
coverage) and the Company is not obligated to make any further payments toward COBRA premiums after such date.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.75in">b.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>The Executive acknowledges and agrees that the value of the Severance Payment and COBRA Benefit is greater than the value of any
other payments or benefits to which the Executive otherwise might be entitled and, except as expressly provided in this Separation Agreement,
the Company and the Releasees have fully satisfied any and all obligations owed to the Executive arising out of or relating to the Executives&rsquo;s
employment or other relationship with the Company or any of the other Releasees, and no further sums, payments or benefits are owed to
the Executive by the Company or any of the Releasees arising out of or relating to Executive&rsquo;s employment or other relationship
with the Company or any of the other Releasees.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.75in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">4.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Termination of Benefit Plan Participation; Equity Awards</B>. Whether or not the Executive signs and returns this Separation
Agreement, the Executive&rsquo;s participation, and, if applicable, the Executive&rsquo;s dependent(s)&rsquo; coverage, under all employee
benefit plans sponsored by the Company shall end as of the Separation Date; <U>provided</U>, <U>however</U>, that the Executive shall
receive separate written notification regarding the Executive&rsquo;s right to continue coverage under the Company&rsquo;s group healthcare
benefits plans after the Separation Date at the Executive&rsquo;s and/or the Executive&rsquo;s dependent(s)&rsquo; own expense under COBRA
(other than the COBRA Benefit if applicable). In addition, notwithstanding the terms under the Company&rsquo;s 2014 Long-Term Incentive
Plan and its award agreements and the Company&rsquo;s 2019 Omnibus Incentive Plan and its award agreements (collectively, the &ldquo;<U>Equity
Arrangements</U>&rdquo;), (i) all unvested equity awards held by the Executive under the Equity Arrangements shall immediately terminate
and be forfeited as of the Separation Date and (ii) all vested equity awards held by the Executive under the Equity Arrangements shall
be treated in accordance with the terms of the Equity Arrangements as of the Separation Date.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">5.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Release</B>.
The Executive, for and on behalf of himself and his executors, administrators, successors and assigns, hereby irrevocably and
unconditionally releases the Company together with its parents, subsidiaries, co-venturers and affiliates, and each of its
respective predecessors, successors and assigns, and all of those entities&rsquo; current and former partners, shareholders,
members, owners, heirs, assigns, employees, agents, officers, directors, attorneys, and insurers, but only in their capacities as
such (collectively, &ldquo;<U>Releasees</U>&rdquo;) from any and all rights, claims, charges, actions, causes of action, complaints,
sums of money, suits, debts, covenants, contracts, agreements, promises, obligations, damages, demands or liabilities of every kind
whatsoever, in law or in equity, whether known or unknown, suspected or unsuspected (collectively, &ldquo;<U>Claims</U>&rdquo;)
which the Executive or his heirs, executors, administrators, successors or assigns ever had, now has or may hereafter claim to have
by reason of any matter, cause or thing whatsoever arising out of or relating in any way to the Executive&rsquo;s employment
relationship, or termination of the Executive&rsquo;s employment or services, with the Company or any of the other Releasees,
including, but not limited to, any such Claims: (i) arising from the beginning of time through the date upon which the Executive
signs this Separation Agreement, including, but not limited to, any such Claims (A) arising out of or relating to the termination of
the Executive&rsquo;s employment with the Company, (B) arising out of or relating to tort, fraud or defamation, and (C) arising
under any federal, state, local or foreign statute or regulation, including, without limitation, the Age Discrimination in
Employment Act of 1967, as amended by the Older Workers Benefit Protection Act (the &ldquo;<U>ADEA</U>&rdquo;), Title VII of the
Civil Rights Act of 1964, the Americans with Disabilities Act of 1990, the Executive Retirement Income Security Act of 1974, the New
York State Human Rights Law, the New York State Labor Law, the New York State Worker Adjustment and Retraining Notification Act, the
New York State Corrections Law, and the New York Executive Law Section 296(15), employment discrimination under the Minnesota Human
Rights Act, pay discrimination under the Minnesota Equal Pay for Equal Work law, all as amended and including all of their
respective implementing regulations and/or any other federal, state, local or foreign law (statutory, regulatory or otherwise) that
may be legally waived and released; (ii) relating to wrongful employment termination; or (iii) arising under or relating to any
policy, agreement, understanding or promise, written or oral, formal or informal, between the Company or any of the other Releasees
and the Executive, including, without limitation, the Employment Agreement; <U>provided</U>, <U>however</U>, that notwithstanding
the foregoing, nothing contained in this Section&nbsp;5 shall in any way diminish or impair: (I) any rights the Executive may have
to vested benefits under employee health and welfare benefit plans; (II) the Executive&rsquo;s ability to bring proceedings to
enforce this Separation Agreement; (III) the Executive&rsquo;s right to challenge the validity of the release of ADEA claims set
forth in this Separation Agreement; (IV) any Claims the Executive may have that cannot be waived under applicable law, such as
unemployment benefits, workers&rsquo; compensation and disability benefits, (V) any rights the Executive may have to bring any Claim
for indemnification or legal defense under any applicable directors and officers liability insurance policy, prior agreements or
policies, by-laws or applicable common, state or federal law, or (VI) the Executive&rsquo;s right to file a charge with or
participate in a charge by the Equal Employment Opportunity Commission, the New York State Division of Human Rights or any other
local, state, or federal administrative body or government agency that is authorized to enforce or administer laws related to
employment; <U>provided</U> that the Executive hereby waives the right to recover any monetary damages or other relief against any
Releasee with respect to Claims released by the Executive herein.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" WIDTH="100%" STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt"><TR STYLE="vertical-align: top">
<TD STYLE="width: 0.5in"></TD><TD STYLE="width: 0.5in">6.</TD><TD STYLE="text-align: justify"><B>Consultation with Attorney/Voluntary Agreement. </B></TD></TR></TABLE>

<P STYLE="margin-top: 0pt; margin-bottom: 0pt; font: 10pt Times New Roman, Times, Serif">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">a.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>The
Executive acknowledges that (i) the Company has advised the Executive to consult with an attorney of the Executive&rsquo;s choosing
before signing this Separation Agreement, (ii) the Executive has been given the opportunity to seek the advice of counsel and has,
in fact, obtained the advice of sophisticated counsel, (iii) the Executive has carefully read and fully understands all of the
provisions of this Separation Agreement, (iv) the release provided herein specifically applies to any rights or claims the Executive
may have against the Releasees pursuant to the ADEA, (v) the Executive is entering into this Separation Agreement knowingly, freely
and voluntarily in exchange for good and valuable consideration to which the Executive is not otherwise entitled, including the
payments and benefits set forth in Section 3 of this Separation Agreement, and (vi) the Executive has the full power, capacity and
authority to enter into this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">b.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>The Executive understands and agrees that the Executive has been given at least twenty-one (21) calendar days following the Executive&rsquo;s
receipt of this Separation Agreement (on June 7, 2022) to consider whether to sign this Separation Agreement, although the Executive may
sign it sooner. <B><U>In no event shall the Executive sign this Separation Agreement prior to the Separation Date.</U></B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">c.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>For a period of fifteen (15) days after the date on which the Executive signed it, the Executive may, in the Executive&rsquo;s
sole discretion, revoke this Separation Agreement by delivering a written notice of rescission to the Company by email to Allison Kiene
at Allison.Kiene@argogroupus.com by no later than 5:00 p.m. ET of the fifteenth (15th) day following the Executive&rsquo;s execution of
this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">d.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>In the event of such revocation by the Executive, the release in Section 5 of this Separation Agreement shall be of no force or
effect, and the Company&rsquo;s obligations to make the payment set forth in Section 3 above shall be null and void. If the Executive
does not revoke this Separation Agreement pursuant to this Section&nbsp;6, this Separation Agreement shall become final and binding and
shall be irrevocable on the eighth (8th) calendar day following the date of the Executive&rsquo;s execution of this Separation Agreement
(such date, the &ldquo;<U>Effective Date</U>&rdquo;). Changes to this Separation Agreement made after the Executive&rsquo;s receipt of
this Separation Agreement, whether material or immaterial, shall not restart the running of the twenty-one (21) calendar day consideration
period.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">7.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Restrictive Covenants</B>. Except as modified by Section 8 of this Separation Agreement, the Executive acknowledges and agrees
that the covenants set forth in Sections 8 and 9 of the Employment Agreement are incorporated herein by reference and fully made a part
hereof as if executed in connection with this Separation Agreement on the Effective Date, and remain in full force and effect in accordance
with their terms.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">8.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Permitted
Disclosures</B>. Pursuant to 18 U.S.C. &sect; 1833(b), the Executive hereby acknowledges that the Executive shall not have criminal
or civil liability under any federal or state trade secret law for the disclosure of a trade secret that (i) is made (A) in
confidence to a federal, state, or local government official, either directly or indirectly, or to an attorney and (B) solely for
the purpose of reporting or investigating a suspected violation of law; or (ii) is made in a complaint or other document that is
filed under seal in a lawsuit or other proceeding. The Executive understands that if the Executive files a lawsuit for retaliation
by the Company for reporting a suspected violation of law, he may disclose the trade secret to the Executive&rsquo;s attorney and
use the trade secret information in the court proceeding if the Executive (x) files any document containing the trade secret under
seal, and (y) does not disclose the trade secret, except pursuant to court order. Nothing in this Separation Agreement or any other
agreement by and between the Company and the Executive is intended to conflict with 18 U.S.C. &sect; 1833(b) or create liability for
disclosures of trade secrets expressly allowed by such section. Further, notwithstanding anything to the contrary contained in this
Separation Agreement, this Separation Agreement does not prohibit or restrict the Executive from (i) voluntarily communicating with
an attorney retained by the Executive, (ii) voluntarily communicating with any law enforcement, government agency, including the
Securities and Exchange Commission (&ldquo;<U>SEC</U>&rdquo;), the Equal Employment Opportunity Commission, the New York State
Division of Human Rights or a local commission on human rights, or any self-regulatory organization, regarding possible violations
of law, in each case without advance notice to the Company, or otherwise initiating, testifying, assisting, complying with a
subpoena from, or participating in any manner with an investigation conducted by such government agency, (iii) recovering a SEC
whistleblower award as provided under Section 21F of the Securities Exchange Act of 1934, (iv) disclosing any Confidential
Information to a court or other administrative or legislative body in response to a subpoena, <U>provided</U> that the Executive
first promptly notifies and provides the Company with the opportunity to seek, and join in its efforts at the sole expense of the
Company, to challenge the subpoena or obtain a protective order limiting its disclosure, or other appropriate remedy, or (v) filing
or disclosing any facts necessary to receive unemployment insurance, Medicaid or other public benefits to which the Executive is
entitled.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">9.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Cooperation</B>. The Executive acknowledges and agrees that the Executive will assist and cooperate with the Company in connection
with any investigation, proceeding, dispute, or claim that may be made against, by, or with respect to the Company, or in connection with
any ongoing or future investigation, proceeding, dispute, or claim of any kind involving the Company, including any proceeding before
any arbitral, administrative, regulatory, self-regulatory, judicial, legislative, or other body or agency (including, but not limited
to, making himself available upon reasonable notice for factual interviews, preparation for testimony, providing affidavits, and similar
activities), to the extent such claims, investigations, or proceedings relate to the Executive&rsquo;s employment with the Company, services
performed or required to be performed by the Executive, or pertinent knowledge possessed by the Executive.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">10.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>No Admission of Wrongdoing</B>. Neither by offering to make, nor by making, this Separation Agreement, do any of the Parties
admit any failure of performance, wrongdoing, or violation of law. Neither this Separation Agreement nor any of its terms may be used
as an admission or introduced as evidence as to any issue of law or fact in any proceeding, suit or action, other than an action to enforce
this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">11.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Governing Law</B>. This Separation Agreement shall be construed in accordance with, and governed by, the laws of the State of
New York, without regard to the conflict of law principles of any jurisdiction.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">12.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Jurisdiction and Venue</B>. Any action or proceeding arising out of or relating to this Separation Agreement shall be instituted
in the courts located in the United States District Court for the Southern District of New York, or, if such court would not have jurisdiction
over the matter, then only in a New York State court sitting in the Borough of Manhattan, New York. Each Party irrevocably submits to
the exclusive jurisdiction of such courts. As an exception to the exclusive jurisdiction and venue set forth in the preceding sentence,
the Company may seek equitable or injunctive relief against the Executive in any jurisdiction necessary to protect the Company&rsquo;s
rights.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">13.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Waiver
of Jury Trial</B>. <B>THE PARTIES TO THIS SEPARATION AGREEMENT EACH HEREBY WAIVE, TO THE FULLEST EXTENT PERMITTED BY LAW, ANY RIGHT
TO TRIAL BY JURY OF ANY CLAIM, DEMAND, ACTION, OR CAUSE OF ACTION (i) ARISING UNDER THIS SEPARATION AGREEMENT OR (ii) IN ANY WAY
CONNECTED WITH OR RELATED OR INCIDENTAL TO THE DEALINGS OF THE PARTIES HERETO IN RESPECT OF THIS SEPARATION AGREEMENT OR ANY OF THE
TRANSACTIONS RELATED HERETO, IN EACH CASE WHETHER NOW EXISTING OR HEREAFTER ARISING, AND WHETHER IN CONTRACT, TORT, EQUITY, OR
OTHERWISE. THE PARTIES TO THIS SEPARATION AGREEMENT EACH HEREBY AGREE AND CONSENT THAT ANY SUCH CLAIM, DEMAND, ACTION, OR CAUSE OF
ACTION SHALL BE DECIDED BY COURT TRIAL WITHOUT A JURY AND THAT THE PARTIES TO THIS SEPARATION AGREEMENT MAY FILE AN ORIGINAL
COUNTERPART OF A COPY OF THIS SEPARATION AGREEMENT WITH ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF THE PARTIES HERETO TO THE
WAIVER OF THEIR RIGHT TO TRIAL BY JURY.</B></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">14.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Amendments; Waivers</B>. No provision of this Separation Agreement may be changed, extended, waived, modified, discharged or
terminated, except by a written instrument executed by the Parties which expressly states it is an amendment.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">15.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Entire Agreement</B>. This Separation Agreement sets forth the entire understanding between the Company and the Executive, and
supersedes all prior and contemporaneous agreements, representations, discussions and understandings concerning the subject matter addressed
herein; <U>provided</U>, <U>however</U>, that this Separation Agreement shall not supersede or otherwise affect the validity of Sections
8 and 9 of the Employment Agreement. The Company and the Executive represent that, in executing this Separation Agreement, each Party
has not relied upon any representation or statement made by any other Party, other than those set forth herein, with regard to the subject
matter, basis or effect of this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">16.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Section 409A</B>.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">a.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>The intent of the parties is that payments and benefits under this Separation Agreement comply with Section 409A of the Internal
Revenue Code of 1986, as amended, and the regulations and guidance promulgated thereunder (&ldquo;Section 409A&rdquo;), to the extent
subject thereto, and accordingly, to the maximum extent permitted, this Separation Agreement shall be interpreted and administered to
be in compliance therewith. Notwithstanding anything contained in this Separation Agreement to the contrary, the Executive shall not be
considered to have terminated employment with the Company for purposes of any payments under this Separation Agreement which are subject
to Section 409A until the Executive has incurred a &ldquo;separation from service&rdquo; from the Company within the meaning of Section
409A. Each amount to be paid or benefit to be provided under this Separation Agreement shall be construed as a separate and identified
payment for purposes of Section 409A. To the extent required in order to avoid an accelerated or additional tax under Section 409A, amounts
reimbursable to the Executive under this Separation Agreement shall be paid to the Executive on or before the last day of the year following
the year in which the expense was incurred and the amount of expenses eligible for reimbursement (and in-kind benefits provided to the
Executive) during one year may not affect amounts reimbursable or provided in any subsequent year.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">b.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>If
the Executive is required to pay taxes under Section 409A in respect of the Severance Payment, the Company shall promptly pay the
Executive the amount or amounts (a &ldquo;Tax Payment&rdquo;) that are necessary to place the Executive in the same after-tax
financial position that the Executive would have been in if the Severance Payment had not been taxed under Section 409A.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">c.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>The Executive will notify the Company in writing of any claim by the Internal Revenue Service that, if successful, would require
the payment by the Company of the Tax Payment. Such notification shall be given as soon as practicable but no later than ten (10) business
days after the Executive is informed in writing of such claim and shall apprise the Company of the nature of such claim and the date on
which such claim is requested to be paid. The Executive will not pay such claim prior to the expiration of the thirty (30) day period
following the date on which the Executive gives such notice to the Company. If the Company notifies the Executive in writing prior to
the expiration of such period that it desires to contest such claim, the Executive will (i) give the Company any information reasonably
requested by the Company relating to such claim; (ii) take such action in connection with contesting such claim as the Company shall reasonably
request in writing from time to time, including, without limitation, accepting legal representation with respect to such claim by counsel
selected by the Company; (iii) cooperate with the Company in good faith in order to effectively contest such claim; and (iv) permit the
Company to participate in any proceedings relating to such claim. The Company shall bear and pay directly all costs and expenses (including
legal fees and additional interest and penalties) incurred in connection with such contest and shall indemnify and hold the Executive
harmless, on an after-tax basis, for any interest and penalties imposed as a result of such representation and payment of costs and expenses</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">d.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT>Without limitation on the foregoing, the Company shall control all proceedings taken in connection with such contest and, at its
sole option, may pursue or forego any and all administrative appeals, proceedings, hearings and conferences with the taxing authority
in respect of such claim and may, at its sole option, either direct the Executive to pay the tax claimed and sue for a refund or contest
the claim in any permissible manner, and the Executive agrees to prosecute such contest to a determination before any administrative tribunal,
in a court of initial jurisdiction and in one or more appellate courts, as the Company shall determine; provided, however, that if the
Company directs the Executive to pay such claim and sue for a refund, the Company shall advance the amount of such payment to the Executive,
on an interest-free basis, and shall indemnify and hold the Executive harmless, on an after-tax basis, from any income tax (including
interest or penalties with respect thereto) imposed with respect to such advance or with respect to any imputed income with respect to
such advance. The Company&rsquo;s control of the contest shall be limited to issues with respect to which a Tax Payment would be payable
hereunder and the Executive will be entitled to settle or contest, as the case may be, any other issue raised by the Internal Revenue
Service or any other taxing authority.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 1in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">17.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Titles and Headings</B>. Titles and headings to sections, subsections and sub-subsections of this Separation Agreement are for
the purposes of reference only and shall not affect the interpretation of this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">18.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Each Party the Drafter</B>. This Separation Agreement, and the provisions contained in it, shall not be construed or interpreted
for, or against, any party to this Separation Agreement because that party drafted or caused that party's legal representatives to draft
any of its provisions.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left"></P>

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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">19.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Legally
Binding</B>. All of the terms contained in this Separation Agreement (including, without limitation, the &ldquo;whereas&rdquo; clauses)
are contractual, and not a mere recital.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">20.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Construction and Severability</B>. Whenever possible, each provision of this Separation Agreement shall be construed and interpreted
in such manner as to be effective and valid under applicable law, but if any provision of this Separation Agreement is held to be prohibited
by, or invalid, illegal or unenforceable in any respect under, any applicable law or rule in any jurisdiction, such prohibition, invalidity,
illegality or unenforceability shall not affect any other provision of this Separation Agreement or any other jurisdiction, and the Parties
undertake to implement all efforts which are necessary, desirable and sufficient to amend, supplement or substitute all and any such prohibited,
invalid, illegal or unenforceable provisions with enforceable and valid provisions in such jurisdiction which would produce as nearly
as may be possible the result previously intended by the parties without renegotiation of any material terms and conditions stipulated
herein.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">21.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Counterparts</B>. This Separation Agreement may be executed and delivered in counterparts, each of which when so executed and
delivered shall be the original, but such counterparts together shall constitute but one and the same instrument. Signature pages delivered
electronically, including by facsimile or as a PDF attachment to electronic mail, shall be binding to the same extent as an original.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">22.<FONT STYLE="font-family: Times New Roman, Times, Serif; font-size: 10pt">&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;</FONT><B>Successors and Assigns</B>. This Separation Agreement shall inure to the benefit of and be binding upon the Company and any
successor organization which shall succeed to the Company by merger or consolidation or operation of law, or by acquisition of assets
of the Company. The Executive may not assign his duties or obligations under this Separation Agreement.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center; text-indent: 0in"><B><I>[Signature Page Follows]</I></B></P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin-top: 0pt; margin-bottom: 0pt; text-align: left">&nbsp;</P>




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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">IN WITNESS WHEREOF, the Parties
hereto have signed this Separation Agreement as of the dates specified below.</P>

<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: justify; text-indent: 0.5in">&nbsp;</P>

<TABLE CELLPADDING="0" CELLSPACING="0" STYLE="font-size: 10pt; border-collapse: collapse; width: 100%">
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: bold 10pt Times New Roman, Times, Serif">Argo Group International Holdings, Ltd.</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt; width: 50%">&nbsp;</TD>
    <TD STYLE="font: 10pt Times New Roman, Times, Serif; width: 3%">By:</TD>
    <TD STYLE="border-bottom: Black 1pt solid; font: 10pt Times New Roman, Times, Serif; padding-left: 0.125in; width: 47%"> /s/ Susan Comparato</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">Name: Susan Comparato</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">Title: Chief Administrative Officer</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">Date: June 23, 2022</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: bold 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: bold 10pt Times New Roman, Times, Serif">Executive:</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">&nbsp;</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="border-bottom: Black 1pt solid; padding-left: 0.125in; font: 10pt Times New Roman, Times, Serif">/s/ Kevin J. Rehnberg</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">Kevin J. Rehnberg</TD></TR>
  <TR STYLE="font-size: 10pt; vertical-align: bottom">
    <TD STYLE="font-size: 10pt">&nbsp;</TD>
    <TD COLSPAN="2" STYLE="font: 10pt Times New Roman, Times, Serif">Date: June 23, 2022</TD></TR>
  </TABLE>


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<P STYLE="font: 10pt Times New Roman, Times, Serif; margin: 0pt 0; text-align: center">[<I>Signature Page &ndash; Separation Agreement</I>]</P>

<P STYLE="margin: 0">&nbsp;</P>

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