3Q 2023 Earnings Call Presentation

Third Quarter 2023 Earnings

October 30, 2023

Earnings Call Presentation - 3Q 2023

Preliminary Matters

Cautionary Statements Regarding Forward-Looking Information

This presentation may contain or incorporate by reference information that includes or is based on forward-looking statements within the meaning of the safe-harbor provisions of the Private Securities Litigation Reform Act of 1995. We caution investors that these forward-looking statements are not guarantees of future performance, and actual results may differ materially. Such statements involve known and unknown risks, uncertainties, and other factors, including but not limited to:

• changes in the frequency and severity of insurance claims;
• claim development and the process of estimating claim reserves;
• the impacts of inflation;
• changes in interest rate environment;
• supply chain disruption;
• product demand and pricing;
• effects of governmental and regulatory actions;
• litigation outcomes and trends;
• investment risks;
• cybersecurity risks;
• impact of catastrophes; and
• other risks and uncertainties detailed in Kemper's Annual Report on Form 10-K and subsequent filings with the Securities and Exchange Commission ("SEC").

Kemper assumes no obligation to publicly correct or update any forward-looking statements as a result of events or developments subsequent to the date of this presentation.

Non-GAAP Financial Measures

This presentation contains non-GAAP financial measures that the company believes are meaningful to investors. Non-GAAP financial measures have been reconciled to the most comparable GAAP financial measure.

Leading Insurer Empowering Specialty and Underserved Markets

Enabled by a dynamic, diverse and innovative team who act like owners

Target top quartile value creation for customers, employees and shareholders

Third Quarter 2023 Summary

Underlying combined ratio improved sequentially as expected

3rd Quarter

Results

Actions Taken

Balance Sheet

Strength

Profit restoration continues with improvement in underlying results

• Net loss attributable to Kemper Corporation of $146 million ($2.28/sh) - includes $56 million ($0.87/sh) related to termination of Kemper's remaining pension plan obligations
• Adjusted consolidated net operating loss1 of $28 million ($0.44/sh)
• Specialty P&C underlying combined ratio improved sequentially by 1.5 points to 100.5%
• • Offset by prior year adverse reserve development of $78 million
• Life business continues to produce stable earnings
• Total pre-tax current year catastrophe losses of $7 million2

Aggressively pursuing profit restoration

• Specialty P&C Private Passenger Auto actions:
• • New business restrictions continue
  • Filed an additional 6% increase on 13% of the book
  • California rate approval of ~30 points effective in August; earn-in to accelerate in 4Q'23 and beyond
  • Reciprocal Exchange established and first policies written
• LAE, expense and real estate initiatives in line to meet or exceed planned targets
• Preferred P&C2 - wind-down initiated; segment results now reported in Non-Core Operations

Capital and liquidity positions enable the company to navigate the current environment

• Holding company liquidity of approximately $800 million3 remains a source of strength for subsidiaries
• Insurance companies are well capitalized

4

Third Quarter 2023 Financial Summary

Focus remains on restoring business to profitability

Quarter Ended

Specialty P&C Reserve Update

Adverse development driven by PIP, Bodily Injury, and Property Damage coverages

Specialty P&C1 adverse development of $78 million

• Private Passenger Auto adverse development of $71 million related to:
• • Florida Personal Injury Protection (PIP), mainly from policy periods 2020-2022o Increased frequency and severity of litigated claims
  • Bodily Injury and Property Damage loss activity during the second half of 2022o Extended development patterns
    o Changes in claim mix and treatment patterns o More claims closing with payment
• Commercial Vehicle development of $7 million
• • Primarily related to Bodily Injury claims

Continue to recognize and react to changes in loss patterns

Strategic Initiatives Summary

Projects proceeding to expectations

1. Bermuda Optimization:
2. • Anticipate $250+ million in Life dividends to parent in 4Q'23
3. Pension Plan Termination:
4. • Recognized $56 million after-taxnon-cash charge to settle remaining pension plan obligations (previously recognized in AOCI)
   • Reduces tail risk and expenses
5. Preferred P&C¹ Exit:
6. • Wind-downis proceeding as planned; will redeploy greater than $300 million in capital
   • • Anticipate a release of $175+ million of capital by year-end 2024 and additional $100+ million by year- end 2025
7. Streamlining Cost Structure(see page 8)
8. Reciprocal Exchange(see page 9)

On track to realize benefits of strategic initiatives

Streamlining Our Cost Structure

Advancing differentiated capabilities to strengthen systematic, sustainable competitive advantages

Real estate and enterprise expense initiatives met program objectives; LAE improvements on track

Reciprocal Exchange

The Exchange began writing auto policies in Illinois during the quarter

Creation Phase Complete

• Reciprocal Exchange structure established and operating
• First auto policies written in 3Q'23
• Special topic call on Reciprocal Exchange structure and financial reporting to be held in 1Q'24

Population Strategy

• Direct premium / policy issuance underway in Illinois
• Exchange reinsurance beginning in 2024
• • Reinsuring select new business from existing Kemper legal entities accelerates Exchange premium growth
• Additional premium to be directly written on Exchange forms in 2024 and 2025 as products / forms are filed and approved

Reciprocal Exchange operational with plans for expansion underway

Well-Capitalized Insurance Subsidiaries

Initiatives underway to restore profitability and operating cash flow