Maiden : Investor Update – November 2023

Maiden Holdings, Ltd.

Third Quarter 2023 Investor Presentation

November 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 nine months ended September 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 Q3 2023 Highlights

• Adjusted book value was $3.16 per share as of September 30, 2023

1. Adjusted book value decreased by $0.06 per common share due mainly to net loss available to Maiden common shareholders of $3.5m in Q3 2023

• 1. Reported book value per common share was $2.60 per share as of September 30, 2023
• GAAP net loss available to common shareholders was $3.5m or $0.03 per share
• 1. Stronger investment results offset by higher underwriting loss

1. Investment results were 145% higher in Q3 2023 compared to Q3 2022 primarily due

to increases in interest income from higher yielding floating rate investments

• Income from equity method investments of alternative asset portfolio were $2.2m in Q3 2023

1. Adverse prior year loss development of $7.8m from both segments in Q3 2023
2. • Bulk of adverse development for Q3 2023 from AmTrust Hospital Liability ($6.0m) which is not covered by Enstar LPT/ADC
   • See slide 5-6 for details on Q3 and YTD underwriting results and loss development by segment

• 1. Operating expenses $0.3m or 4.6% higher than Q3 2022
• Asset management activity reflects focus on assets producing current income
• 1. Alternative portfolio increased by 8.4% during Q3 2023 primarily as a result of funding commitments in real estate, private equity, and private credit asset classes

• 1. Despite uneven market conditions, alternative assets remain on track to exceed benchmark returns, though it remains too early to begin assessing performance for many fund investments
• Full valuation allowance maintained on U.S. deferred tax asset of $1.20 per share at 9/30/2023
• 1. Not recognized as an asset on balance sheet currently

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

1. 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 - Q3 2023 Results Recap

($ millions, except per share amounts)	Q3 2023	Q3 2022	Comments
			Net Income and Per Share Data
GAAP Net (Loss) Income (Attributable)	$(3.5)	$(8.2)	• Improvement driven by higher investment results and lower underwriting loss offset by
Available to Common Shares			lower foreign exchange and other gains
Per common share	$(0.03)	$(0.09)	• Summary GAAP and Non-GAAP Financial Measures in Appendix
			Key Income Statement Details
Underwriting Loss	$(10.9)	$(12.6)	• Decline in underwriting loss in quarter, AmTrust segment had underwriting loss of $8.4m
			while Diversified Reinsurance segment had underwriting loss of $2.5m
			• Adverse prior year development in Q3 2023of $7.8m from AmTrust ($6.0m) and
			Diversified ($1.9m) segments - Q3 2022 had consolidated adverse prior year development
			of $0.8m
			• Most of the adverse development in Q3 2023 is from Hospital Liability which is not subject
			to the Enstar LPT/ADC
			• See slide 5 for detail on underwriting results and prior period loss development
Investment Results	$11.5	$4.7	• Net investment income 36.3% higher at $9.1m in Q3 2023 vs. $6.6m in Q3 2022 as income
			received on floating rate AmTrust loan as well as income from AFS securities increased
			• Realized and unrealized gains of $0.2m in Q3 2023 vs. losses of $1.6m in Q3 2022 mainly
			attributable to gains on equity securities & other investments offset by realized losses on
			sales of AFS securities
			• Income from equity method investments of $2.2m vs. loss of $0.4m in Q3
			2022 mainly attributable to investments in the alternative & private equity asset classes
Operating Expenses	$6.8	$6.5	• Operating expenses increased slightly, by $0.3m or 4.6% vs. Q3 2022 due to increase in
			payroll, audit and LOC fees
Foreign Exchange/Other Gains	$4.6	$8.6	• Primarily due to reserve revaluation due to weakening of U.S. dollar relative to Euro and
			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 Q3 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)	$(17.8)	$19.2	• Net income attributable to Maiden common shareholders in YTD Q3 2022 includes
Available to Common Shares			$28.2m of gains from purchases of preference shares
Per common share	$(0.18)	$0.22	• Summary GAAP and Non-GAAP Financial Measures in Appendix
GAAP Net Loss	$(17.8)	$(9.0)	• Higher Q3 2023 net loss compared to Q3 2022 resulted from higher underwriting loss and
(excl. preference share gains)			lower foreign exchange and other gains offset by higher investment results
			Key Income Statement Details
Underwriting Loss	$(28.4)	$(19.4)	• Higher underwriting loss in both the AmTrust and Diversified segments
			• Adverse prior year development of $16.0m in nine months ended September 30, 2023,
			from AmTrust segment ($12.0m) and Diversified segment ($3.9m)
			• The comparable nine months to September 2022 had favorable prior year development of
			$5.5m on consolidated basis
			• See slide 6 for detail on underwriting results and prior period loss development
Investment Results	$38.4	$21.6	• Net investment income 39.5% higher at $29.1m in YTD 2023 vs. $20.9m in YTD Q3 2022 as
			income received on floating rate AmTrust loan, AFS securities, and other income
			producing alternative assets increased
			• Realized and unrealized gains of $2.4m in YTD 2023 vs. $2.8m in YTD 2022 mainly
			attributable to gains on equity securities and other investments offset by realized losses
			on sales of AFS securities
			• Income from equity method investments of $6.9m in Q3 2023 vs. loss of $2.1m in YTD Q3
			2022 mainly attributable to investments in the alternative & private equity asset
			classes, as well as improved results in hedge fund investments compared to Q3 2022
Operating Expenses	$23.7	$24.7	• Operating expenses continued to trend lower as G&A expenses decreased by $0.9m, or
			3.8% in Q3 2023 vs. Q3 2022 due mainly to lower stock-based compensation
Foreign Exchange/Other (Losses)	$(0.8)	$19.1	• Primarily due to reserve revaluation due to weakening of U.S. dollar relative to British
Gains			pound; offset by strengthening of U.S. dollar relative to Euro.

* 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

Q3 2023 UW Results and Loss Development

LOSS DEVELOPMENT

(in thousands ('000))

QTD		Sep-23		Sep-22		Variance
Diversified
GLS	$	(40)	$	(477)	$	437
IIS		1,232		(351)		1,583
Motors		(225)		-		(225)
Run-Off		897		238		659
Unfavorable (favorable)		1,864		(590)		2,454
AmTrust
Master QS		(22)		(4,572)		4,550
Hospital Liability		6,012		5,996		16
Other Run-off		(20)		-		(20)
Unfavorable (favorable)		5,970		1,424		4,546
Total Unfavorable (favorable)	$	7,834	$	834	$	7,000

• Underwriting loss of $10.9m in Q3 2023 vs.

$12.6m in Q3 2022

1. $7.8m of adverse prior year loss development in Q3 2023 compared to $0.8m of adverse prior year loss

development in Q3 2022

1. AmTrust had adverse loss development of $6.0m in Q3 2023 compared to $1.4m in Q3 2022
2. • Net adverse prior year loss development in Q3 2023 was primarily due to $6.0m in unfavorable development in Hospital Liability on accident years prior to 2016 as losses emerged
   • CLD Auto and General Liability had more modest adverse development which was mostly offset by continued favorable development
     in Workers' Compensation

1. Diversified had adverse loss development of $1.9m in Q3 2023 compared to favorable development of $0.6m in Q3 2022
2. • Adverse prior year development mostly due to German auto contract and development in other runoff business lines

5

YTD 2023 UW Results and Loss Development

LOSS DEVELOPMENT

(in thousands ('000))

YTD		Sep-23		Sep-22		Variance
Diversified
GLS	$	(24)	$	(1,302)	$	1,278
IIS		1,792	$	(1,830)		3,622
Motors		(10)	$	-		(10)
Run-Off		2,180	$	1,157		1,023
Unfavorable (favorable)		3,938		(1,975)		5,913
AmTrust
Masters QS		6,414		(9,514)		15,928
Hospital Liability		5,992		5,996		(4)
Other Run-off		(360)		-		(360)
Unfavorable (favorable)		12,046		(3,518)		15,564
Total Unfavorable (favorable)	$	15,984	$	(5,493)	$	21,477

• Underwriting loss of $28.4m YTD 2023 vs.

$19.4m YTD 2022

1. $16.0m of adverse prior year loss development in

Q3 2023 compared to $5.5m of favorable prior year loss development in Q3 2022

1. AmTrust segment had adverse loss development of $12.0m in the nine months ended September 2023 compared to favorable development of $3.5m in the same period in 2022
2. • Adverse prior year loss development on AmTrust contracts in 2023 was primarily due to unfavorable movements in Hospital Liability, CLD Auto and General Liability, Specialty Risk and Warranty (structural and construction defect), partly offset by continued favorable

development in Workers Compensation

1. Diversified segment had adverse loss development of $3.9m in the nine months ended September 2023 compared to favorable loss development of $2.0m in the same period in 2022
2. • Adverse prior year development on International business, primarily German Auto contract and other runoff business

6

Maiden Holdings Business Strategy

• We create shareholder value by actively managing and allocating our assets and capital

1. We leverage our deep knowledge of the insurance and related financial services industries into ownership and management of businesses and assets with the opportunity for increased returns

• 1. Change in strategy since 2019 has allowed us to more flexibly allocate capital to activities we believe will produce the greatest returns for our common shareholders
• Our strategy currently has three principal areas of focus
• 1. Asset management - investing in assets and asset classes in a prudent but expansive manner in order to maximize investment returns
  2. • We limit the insurance risk we assume relative to the assets we hold and maintain required regulatory capital at very strong levels to manage our aggregate risk profile

1. Legacy underwriting - judiciously building a portfolio of run-off acquisitions and retroactive

reinsurance transactions which we believe will produce attractive underwriting returns

• 1. Capital management - effectively managing capital and when appropriate, repurchasing securities or returning capital to enhance common shareholder returns
• Strategic focus likely to evolve as market conditions extend timelines for asset management and legacy underwriting target returns to materialize
• 1. Developing more predictable areas of revenue and profit a priority - expanding activities in insurance distribution an area of focus, possibly supplemented by deploying limited reinsurance capacity
• We believe these areas of strategic focus will enhance our profitability
• 1. We believe our strategy increases the likelihood of fully utilizing the significant tax NOL carryforwards which would create additional common shareholder value

1. Expected returns from each strategic pillar are evaluated relative to our cost of debt capital

7

Asset Management Update

8

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

Asset Management Update

Fixed Income

• Q2 fixed income returns primarily driven by higher income from AmTrust loan and AFS securities
  o Short portfolio duration of 1.4 years well positioned for current credit market volatility
  o Higher yields on cash equivalents and floating rate CLOs are offsetting the impact of a smaller portfolio
• Fixed income portfolio continues to decrease in size as AmTrust liabilities continue to run off
  o Payments now being made from Funds Withheld
• Floating rate securities compose $258.8m or 37.7% of fixed income investments which is reducing interest rate risk
  o $87.0m or 12.7% are CLOs which may be credit sensitive
• • Average CLO rating is AA+ with 90.2% rated AAA
  • EUR CLOs of $81.5m yield is 5.7%
  • USD CLOs of $5.5m yield is 8.1%

1. $168.0m or 24.4% is floating rate loan to related party and is priced at Fed Funds rate + 200 basis points
2. • As at 11/7/2023, the current yield of related party loan was 7.3% due to continuing increases in the Fed Funds rate
   • Effective YTD 2023 yield of related party loan is 6.9%

Alternative Investments

• Alternative investments increased by 6.9% to $291.3m at 9/30/2023 compared to $272.5m at 12/31/2022, reflecting increasing focus on current income

producing assets as interest rates continue to rise

• 1. Continued focus on increasing focus to current income producing assets, particularly private credit investments which are yielding private equity like returns
• Year to date total returns on alternative investments for 2023 of $14.2m vs. $6.1m for 2022
• 1. Returns benefitted year over year from unrealized gains in the

private equity asset class as well as income from equity method investments in the alternative asset class

1. Improvements in the broader equity markets led to smaller

losses year over year on investments with equity exposure particularly in the hedge fund asset class

• 1. Interest rate sensitive investments in private credit including those with mortgage exposures continue to face headwinds
• Annualized YTD 2023 gross return of the alternative portfolio of 6.7%
• 1. Still on track to exceed long-term benchmark returns

1. Numerous alternative investments not marked to fair value yet - too early in life cycle of investments

9

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