Maiden : Investor Update – August 2023

Maiden Holdings, Ltd.

Second Quarter 2023 Investor Presentation

August 2023

Investor Disclosures

Forward Looking Statements

This presentation contains "forward-looking statements" which are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. The forward-looking statements are based on Maiden Holdings, Ltd.'s (the "Company") future developments and their potential effects on the Company. There can be no assurance that actual developments will be those anticipated by the Company. Actual results may differ materially from those projected as a result of significant risks and uncertainties, including non-receipt of the expected payments, changes in interest rates, effect of the performance of financial markets on investment income and fair values of investments, developments of claims and the effect on loss reserves, accuracy in projecting loss reserves, the impact of competition and pricing environments, changes in the demand for the Company's products, the effect of general economic conditions and unusual frequency of storm activity, adverse state and federal legislation, regulations and regulatory investigations into industry practices, developments relating to existing agreements, heightened competition, changes in pricing environments, and changes in asset valuations. Additional information about these risks and uncertainties, as well as others that may cause actual results to differ materially from those projected is contained in Item 1A, Risk Factors in the Company's Annual Report on Form 10-K for the year ended December 31, 2022, filed with the SEC on March 15, 2023. The Company undertakes no obligation to publicly update any forward- looking statements, except as may be required by law. Any discrepancies between the amounts included in this presentation and amounts included in the Company's Form 10-Q for the three and six months ended June 30, 2023, filed with the SEC are due to rounding.

Non-GAAP Financial Measures

In addition to the Summary Consolidated Balance Sheets and Consolidated Statements of Income, management uses certain key financial measures, some of which are non-GAAP measures, to evaluate the Company's financial performance and the overall growth in value generated for the Company's common shareholders. Management believes that these measures, which may be defined differently by other companies, explain the Company's results to investors in a manner that allows for a more complete understanding of the underlying trends in the Company's business. The non-GAAP measures should not be viewed as a substitute for those determined in accordance with U.S. GAAP. See the Appendix of this presentation for a reconciliation of the Company's non-GAAP measures to the nearest GAAP measure.

1

Maiden Holdings Q2 2023 Highlights

• Adjusted book value increased to $3.22 per common share while GAAP book value was largely flat at $2.65 per common share

o Adjusted book value increased by $0.10 per common share as effects of adverse loss development and other factors increased the deferred gain related to LPT/ADC

• GAAP net loss available to common shareholders was $2.9m or $0.03 per share o Stronger investment results offset by higher underwriting loss

o Adverse prior year loss development of $4.5m from both segments in Q2 2023  All AmTrust loss development in Q2 covered by Enstar LPT/ADC

 See slide 5-6 for details on Q2 and YTD underwriting results and loss development by segment o Investment results were 144% higher in Q2 2023 due to increases in interest income

 Higher interest from floating rate AmTrust loan and adjustable-rate Funds Withheld as well as gains recognized on certain private equity and alternative investments

o Operating expenses 6.2% lower than Q2 2022

 Expect run rate expenses in Q3 and beyond to reflect continue reduction in range of expenses

• Asset management activity reflect focus on assets producing current income

o Alternative portfolio increased by 1.9% in Q2 reflecting slower deployment as markets remain uncertain and rising interest rates offer opportunity to reallocate to lower risk, income producing assets

o Despite uneven market conditions, alternative assets remain on track to exceed benchmark returns

• Full valuation allowance maintained on U.S. deferred tax asset of $1.17 per share at 6/30/2023

o Not recognized as an asset on balance sheet currently

o Timing of asset recognition likely to be influenced by more stable loss development

o Focus on current income producing assets targets to offset continuing reserve development

2

* Please see the definition of non-GAAP financial measures in the Appendix of this presentation for additional important information regarding certain terms used herein

Maiden Holdings - Q2 2023 Results Recap

($ millions, except per share amounts)	Q2 2023	Q2 2022	Comments
			Net Income and Per Share Data
GAAP Net (Loss) Income (Attributable)	$(2.9)	$25.8	• Net income attributable to Maiden common shareholders in Q2 2022 includes $24.7m of
Available to Common Shares			gains from purchases of preference shares
Per common share	$(0.03)	$0.29	• Summary GAAP and Non-GAAP Financial Measures in Appendix
GAAP Net (Loss) Income	$(2.9)	$1.1	• Q2 2023 net loss resulted from higher underwriting loss and higher foreign exchange and
(excl. preference share gains)			other losses compared to Q2 2022
			Key Income Statement Details
Underwriting Loss	$(9.3)	$(5.1)	• Higher underwriting loss in both the AmTrust Reinsurance and Diversified Reinsurance
			segments in Q2 2023
			• Adverse prior year development of $4.5m in Q2 2023 from AmTrust contracts ($3.2m) and
			Diversified run-off contracts ($1.3m) - Q2 2022 only had adverse prior year development
			of $1.0m
			• AmTrust adverse development in Q2 2023 is covered by Enstar LPT/ADC
			• See slide 5 for detail on underwriting results and prior period loss development
Investment Results	$16.5	$6.7	• Net investment income 37.2% higher at $10.5m in Q2 2023 vs. $7.7m in Q2 2022 as
			income received on floating rate AmTrust loan and adjustable-rate Funds Withheld
			increased
			• Realized and unrealized gains of $1.1m in Q2 2023 vs. $2.1m in Q2 2022 mainly
			attributable to gains on equity securities & other investments offset by losses on AFS
			securities
			• Income from equity method investments of $4.8m vs. loss of $3.0m in Q2
			2022 mainly attributable to investments in the alternative & private equity asset classes,
			as well as improved results in hedge fund investments compared to Q2 2022
Operating Expenses	$6.8	$7.3	• Operating expenses continued to trend lower as G&A expenses decreased by $0.5m, or
			6.2% in Q2 2023 vs. Q2 2022 due to decrease in non-compensation overhead expenses
Foreign Exchange/Other (Losses)	$(2.6)	$6.6	• Primarily due to reserve revaluation due to weakening of U.S. dollar relative to Euro and
Gains			British pound

* Please see the definition of non-GAAP financial measures in the Appendix of this presentation for	3
additional important information regarding certain terms used herein

Maiden Holdings - YTD Q2 2023 Results Recap

	YTD	YTD
($ millions, except per share amounts)	Q2 2023	Q2 2022	Comments
			Net Income and Per Share Data
GAAP Net (Loss) Income (Attributable)	$(14.3)	$27.3	• Net income attributable to Maiden common shareholders in YTD Q2 2022 includes
Available to Common Shares			$28.2m of gains from purchases of preference shares vs. $0 in YTD Q2 2023
Per common share	$(0.14)	$0.31	• Summary GAAP and Non-GAAP Financial Measures in Appendix
GAAP Net Loss	$(14.3)	$(0.9)	• Q2 2023 net loss resulted from higher underwriting loss and higher foreign exchange and
(excl. preference share gains)			other losses compared to Q2 2022 offset by higher investment results
			Key Income Statement Details
Underwriting Loss	$(17.5)	$(6.8)	• Higher underwriting loss from both the AmTrust Reinsurance and Diversified Reinsurance
			segments
			• Adverse prior year development of $8.2m in six months ended June 30, 2023, from
			AmTrust contracts ($6.1m) and Diversified run-off contracts ($2.1m). The comparable six
			months to June 2022 had favorable prior year development of $6.3m
			• AmTrust adverse development in the year is covered by Enstar LPT/ADC
			• See slide 6 for detail on underwriting results and prior period loss development
Investment Results	$27.0	$16.9	• Net investment income 41.0% higher at $20.1m in YTD 2023 vs. $14.2m in YTD 2022 as
			income received on floating rate AmTrust loan and adjustable-rate Funds Withheld
			increased
			• Realized and unrealized gains of $2.2m in Q2 2023 vs. $4.4m in YTD Q2 2022 mainly
			attributable to gains on equity securities and other investments
			• Income from equity method investments of $4.8m in Q2 2023 vs. loss of $1.8m in YTD Q2
			2022 mainly attributable to investments in the alternative & private equity asset
			classes, as well as improved results in hedge fund investments compared to Q2 2022
Operating Expenses	$16.9	$18.2	• Operating expenses continued to trend lower as G&A expenses decreased by $1.2m, or
			6.8% in Q2 2023 vs. Q2 2022 due mainly to lower stock-based compensation
Foreign Exchange/Other (Losses)	$(5.4)	$10.5	• Primarily due to reserve revaluation due to weakening of U.S. dollar relative to Euro and
Gains			British pound

* Please see the definition of non-GAAP financial measures in the Appendix of this presentation for	4
additional important information regarding certain terms used herein