Argo Group Conference Call Supplement

November 2021

ARGO GROUP Earnings Supplement

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Forward-Looking Statements

This presentation may include forward-looking statements, both with respect to Argo Group International Holdings, Ltd. ("Argo Group", "we", or "our") and its industry, that reflect our current views with respect to future events and financial performance. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as "expect," "intend," "plan," "believe," "do not believe," "aim," "project," "anticipate," "seek," "will," "likely," "assume," "estimate," "may," "continue," "guidance," "objective," "remain optimistic," "path toward," "outlook," "trends," "future," "could," "would," "should," "target," "on track" and similar expressions of a future or forward-looking nature.

There can be no assurance that actual developments will be those anticipated by Argo Group. Actual results may differ materially as a result of significant risks and uncertainties including but not limited to the continuing impact of the novel coronavirus pandemic and related economic matters; changes in the pricing environment including those due to the cyclical nature of the insurance industry; increased competition; the adequacy of our projected loss reserves including development of claims that varies from that which was expected when loss reserves were established, adverse legal rulings which may impact the liability under insurance contracts beyond that which was anticipated when the reserves were established, development of new theories related to coverage which may increase liabilities under insurance contracts beyond that which were anticipated when the loss reserves were established, and reinsurance coverage being other than what was anticipated when the loss reserves were established; changes in tax regulations or laws applicable to us, our subsidiaries, brokers or customers; state, federal and foreign regulations that may impede our ability to charge adequate rates and efficiently allocate capital; changes in insurance regulations in the U.S. or other jurisdictions in which we operate; actions by our competitors, many of which are larger or have greater financial resources than we do; the inability to retain key personnel; natural and/or man-made disasters, including terrorist acts; impact of global climate change; changes in the availability, cost or quality of reinsurance or retrocessional coverage; the inability to collect reinsurance recoverables; a downgrade in our financial strength ratings; changes in general economic and/or industry specific conditions, including inflation or deflation, foreign currency exchange rates, interest rates, and other similar factors; changes in the financial markets that impact investment income and the fair market values of our investments; changes in asset valuations; failure to execute information technology strategies; exposure to an information security breach; failure of outsourced service providers; failure to execute on expense targets; inability to successfully execute our business plan, divestitures, mergers or acquisitions; and costs associated with shareholder activism.

For a more detailed discussion of such risks and uncertainties, see Item 1A, "Risk Factors" in Argo Group's Annual Report on Form 10-K for the fiscal year ended December 31, 2020, as supplemented in Part II, Item 1A, "Risk Factors" of Argo Group's subsequent Quarterly Reports on Form 10-Q and in other filings with the Securities and Exchange Commission. The inclusion of a forward-looking statement herein should not be regarded as a representation by Argo Group that Argo Group's objectives will be achieved. Argo Group undertakes no obligation to publicly update forward-looking statements, whether as a result of new information, future events or otherwise. You should not place undue reliance on any such statements.

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Announced Actions Aligned With Strategic Priorities

Q3 2021 Earnings Supplement

U.S. Operations
Exited U.S. Grocery	Sold Renewal Rights to Contract
& Retail	Binding P&C Business

2020	2021		2022
Announced Syndicate	Exited	Exited European	Announced an
1200 Reinsurance-	Reinsurance	Underwriting	Agreement to Sell
To-Close,	Business	Outside of Lloyd's	Brazilian Operations,
2017 and Prior Years	/ Ariel Re		Argo Seguros

International Operations

Note: The timeline above is a directional representation of portfolio related actions that have been formally announced.

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U.S. Pro-Forma Business Profile Post-Portfolio Changes

Q3 2021 Earnings Supplement

U.S. Operations Gross Written Premium (GWP)

$2,250	77.4%					80%
$2,000
	74.0%		$184		75%
$1,750		$193			U.S. Retention
		$64
$1,500	$178	$182							excluding Fronting	• U.S. retention ratio (Net Written Premium
			70%
$1,250				67.8%			U.S. Retention	(NWP) / GWP) has been impacted by
$1,000	68.3%	66.7%	68.6%	67.1%				65%		including Fronting	fronting business
					U.S. Pro-Forma
$750								• Business exits include U.S. Grocery &
									Business GWP
				63.0%					Retail, Contract Binding P&C business and
$500			62.7%	61.3%					Exited Business
							other lines of business that are no longer
$250										GWP
										written
$0						55%
2017	2018	2019	2020	3Q'21-YTD

U.S. Operations Historical Combined Ratio

				U.S. Pro-Forma Business		U.S. Exited Business
				Combined Ratio		Combined Ratio
	113.3%		117.5%	125.3%	120.1%
		108.0%
85.5%		87.9%	90.5%		91.4%	91.8%

2017

2018

2019

2020

3Q'21-YTD

$ in millions

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Int'l Pro-Forma Business Profile Post-Portfolio Changes

Q3 2021 Earnings Supplement

International Operations Gross Written Premium

$1,40058.1% 60%

	52.4%										• Int'l retention ratio (NWP / GWP)
$1,200	$758	$710	$601		55%
					increasing due to strategic repositioning
$1,000
$741	50.6%				50%				of the portfolio towards less CAT-
								Int'l Retention
$800			46.3%	47.4%	$199					exposed lines of business
$600									Exited Business	• Business exits include Ariel Re, Argo
									GWP	Seguros, Brazil and the planned exits of
$400										Int'l Pro-Forma
									businesses in Italy and Malta and reflects
									Business GWP
$200											re-underwritten and / or other lines of
					30%
											business in Syndicate 1200 that are no
$0						25%
2017	2018	2019	2020	3Q'21-YTD				longer written

International Operations Historical Combined Ratio

			Int'l Pro-Forma Business			Int'l Exited Business
			Combined Ratio			Combined Ratio
	129.7%			140.9%
			131.8%		117.8%
	119.3%
99.0%	105.4%	100.7%	96.0%
90.7%

2017

2018

2019

2020

3Q'21-YTD

$ in millions

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