Progressive : August 2016 Loss Reserve Report

Exhibit 99

The artwork1 on the cover of the 2016 Report on Loss Reserving Practices shows a thread tying together a variety of triangles. The thread is a Progressive-wide symbol that ties together our brand, our people, and our customers. The thread runs through us and binds us toward a common goal. In loss reserving, our goal is to accurately set reserves. We tie together data, often in the form of triangles, to reach this goal. The thread runs through us.

The primary purpose of this report is to help interested stakeholders better understand our loss reserving process and how it affects our financial results. Reserves in this report refer to loss and loss adjustment expense reserves.

The 2016 Report on Loss Reserving Practices is very similar to the 2015 report. However, we updated financial information throughout the report.

As the Appendix is a separate document, you can electronically link to it anywhere that you see the blue underlined word: Appendix.

Consistent with Progressive's culture of self-examination, our analysis of loss reserves demands continuous change and continuous improvement. Each section of this report focuses on a different aspect of our reserving process.

• Section I provides an overview of our financial objectives and results, and explains why accurate reserving is important

• Section II defines our overall goal of the reserving process, the different types of reserves, how they are related and how we analyze them

• Section III defines reserve development and describes how it affects our financial results, and also how historical results compare to our goal of having total reserves that are adequate and develop with minimal variation

• Section IV describes how and why we estimate our required reserves by segment

• Section V defines many of the terms we use throughout the report

• Sections VI and VII in the Appendix present two case studies of segment reserve reviews - one for loss reserves and one for Loss Adjustment Expense (LAE) reserves, including discussion of the issues we consider and the calculations involved

The 2016 Report on Loss Reserving Practices was revised by Karen VanCleave. Despite the technical nature of our reserve analysis, we strive to make this report as accessible and understandable as possible to a wide audience. We welcome your comments so that we may continue to enhance it. Comments and questions should be directed to Gary Traicoff, Corporate Actuary or Karen VanCleave, Actuarial Director, at The Progressive Corporation, 6300 Wilson Mills Road, Mayfield Village, Ohio 44143 or e-mailed to gary_traicoff@progressive.com or karen_vancleave@progressive.com.

1 Artwork for the cover of this report was designed by **John Burke.

Safe Harbor Statement Under the Private Securities Litigation Reform Act of 1995: Investors are cautioned that certain statements in this report not based upon historical fact are forward-looking statements as defined in the Private Securities Litigation Reform Act of 1995. These statements often use words such as "estimate," "expect," "intend," "plan," "believe," and other words and terms of similar meaning, or are tied to future periods, in connection with a discussion of future operating or financial performance.

Forward-looking statements are based on current expectations and projections about future events, and are subject to certain risks, assumptions and uncertainties that could cause actual events and results to differ materially from those discussed herein. These risks and uncertainties include, without limitation, uncertainties related to estimates, assumptions, and projections generally; inflation and changes in general economic conditions (including changes in interest rates and financial markets); the accuracy and adequacy of our pricing, loss reserving, and claims methodologies; the competitiveness of our pricing and the effectiveness of our initiatives to attract and retain more customers; our ability to obtain regulatory approval for requested rate changes and the timing thereof and for any proposed acquisitions; legislative and regulatory developments at the state and federal levels, including, but not limited to, matters relating to vehicle and homeowners insurance; the outcome of litigation or governmental investigations that may be pending or filed against us; severe weather conditions and other catastrophe events; the effectiveness of our reinsurance programs; changes in driving and residential occupancy patterns; our ability to accurately recognize and appropriately respond in a timely manner to changes in loss frequency and severity trends; technological advances; court decisions, new theories of insurer liability or interpretations of insurance policy provisions and other trends in litigation; changes in health care and auto and property repair costs; and other matters described from time to time in our releases and publications, and in our periodic reports and other documents filed with the United States Securities and Exchange Commission.

Our Business 1

2015 Business Highlights 1

Our Financial Objectives 1

Relationship between Loss Reserving and Pricing Functions 2

Loss Reserve Uncertainty and Capital Planning 3

Definition and Stated Goals 6

Loss Reserves 7

Case Reserves 7

Incurred But Not Recorded (IBNR) Reserves 10

Loss Adjustment Expense (LAE) Reserves 11

Involuntary Market Operating Loss Reserves 12

Other Considerations to Reserves 12

Calendar Year versus Accident Year 14

Paid Development Patterns 14

Reserve Development 15

External Reporting of Reserve Changes and Reserve Development 17

Internal Reporting of Reserve Changes and Reserve Development 19

Segmentation of Reserves for Analysis 20

Projections of Ultimate Losses 21

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