DIAMOND OFFSHORE DRILLING, INC.

PRELIMINARY PROXY MATERIAL – SUBJECT TO COMPLETION

March 30, 2023

Dear Stockholder:

You are cordially invited to attend the annual meeting of stockholders of Diamond Offshore Drilling, Inc. to be held at the company’s headquarters located at 15415 Katy Freeway, Houston, Texas 77094, on Wednesday, May 10, 2023, at 8:30 a.m. local time. Details regarding the meeting are provided in the accompanying Notice of Annual Meeting of Stockholders and proxy statement. We urge you to read this information carefully.

We would like to highlight several of the ways our Board of Directors and management team have been working on your behalf this past year:

Operational Excellence: During 2022, we were awarded significant new work from our customers at improving dayrates, adding $1.3 billion of new backlog, including a new contract that allowed us to reactivate our ultra-deepwater harsh environment semisubmersible Ocean GreatWhite. In addition, in 2022 we continued operating at high levels of fleet utilization and operating efficiency, while achieving our best safety performance in the last four years.

Robust Stockholder Engagement: In March 2022, we relisted our shares of common stock on the NYSE and expanded our stockholder engagement efforts, meeting with a broad range of stockholders and investors throughout the year. After relisting, our stock price appreciated by more than 38% during the remainder of 2022 and by approximately 49% through our March 14, 2023 annual meeting record date.

Board Composition: Our Board is focused on maintaining a balance of leadership, diverse perspectives, relevant strategic skill sets and professional experience. Seven of our eight current directors (and both of our director nominees for election at the annual meeting) are independent. Diversity at our company is evolving, and our Board is leading by example. Two years ago, our Board did not include any gender, racial or ethnic diversity. Now, over 37% of the directors serving on our Board are either female or racially or ethnically diverse. In addition, in furtherance of our commitment to stockholder rights and strong governance, at the annual meeting we are proposing to amend our Certificate of Incorporation to declassify our Board.

Focus on Operating Responsibly and Sustainably: Both the Board and the Nominating, Governance and Sustainability Committee of the Board are focused on providing strong oversight of the company’s corporate responsibility efforts. During 2022, the company published our first Sustainability Report on our company website and made progress in reducing fuel usage and the carbon footprint of our rigs.

On behalf of the Board and management, we appreciate your trust, support and participation.

DIAMOND OFFSHORE DRILLING, INC.

NOTICE OF ANNUAL MEETING OF STOCKHOLDERS

To Be Held on May 10, 2023

The annual meeting of stockholders of Diamond Offshore Drilling, Inc. will be held at the office of the company located at 15415 Katy Freeway, Houston, Texas 77094, on Wednesday, May 10, 2023, at 8:30 a.m. local time, for the following purposes, as more fully described in the accompanying proxy statement:

Our stockholders of record at the close of business on March 14, 2023 are entitled to notice of, and to vote at, the annual meeting and any adjournments or postponements. Additional information regarding the annual meeting is included in the attached proxy statement. Your vote is important. Whether or not you plan to attend the meeting in person, please vote as promptly as possible using the Internet or telephone as instructed on your enclosed proxy card, or, if you received a paper copy of the proxy materials, by signing, dating and returning the proxy card. The Board of Directors recommends a vote FOR each of the Class II director nominees recommended by your Board on the proxy card, FOR the resolution approving executive compensation, FOR the ratification of the appointment of Deloitte & Touche LLP as our independent auditor for fiscal year 2023 and FOR the amendments to our Certificate of Incorporation to declassify our Board. In addition, our Board recommends to hold an advisory vote on executive compensation EVERY YEAR.

March 30, 2023				By Order of the Board of Directors,
				David L. Roland
				Senior Vice President, General Counsel and Secretary

Important Notice Regarding the Availability of Proxy Materials

for the Annual Meeting of Stockholders to be Held on May 10, 2023:

Our proxy statement, proxy card and 2022 annual report are available at www.proxydocs.com/DO.

Table of Contents

DIAMOND OFFSHORE DRILLING, INC.

PROXY STATEMENT SUMMARY

For the Annual Meeting of Stockholders

to be held on May 10, 2023

This summary is included to provide an introduction and overview of certain of the information in this proxy statement. This is a summary only and does not contain all of the information we have included in this proxy statement. You should refer to the full proxy statement for more information about us and the proposals you are being asked to consider.

ABOUT DIAMOND OFFSHORE

Diamond Offshore Drilling, Inc. (which we refer to in this proxy statement as we, our, us, Diamond Offshore, our company or the company) is a leader in offshore drilling, providing innovation, thought leadership and contract drilling services to solve complex deepwater challenges around the globe. We provide contract drilling services to the energy industry with a fleet of 14 floater rigs (four owned drillships, eight semisubmersibles and two managed rigs). Additional information is available at http://www.diamondoffshore.com/.

DIRECTOR NOMINEES*

Since our emergence from our Chapter 11 reorganization in April 2021, our Board of Directors (or Board) has been classified into three staggered classes, designated as Class I, Class II and Class III, with one class of directors standing for election each year. Upon the recommendation of the Nominating, Governance and Sustainability Committee (or the NG&S Committee), the Board adopted, subject to stockholder approval at our 2023 annual meeting of stockholders (which we refer to as the Annual Meeting), amendments to our Certificate of Incorporation to declassify the Board and institute annual elections of directors on a phased-in basis. See “Approval of Amendments to our Certificate of Incorporation to Declassify our Board (Proposal No. 5).”

Our current Class II directors serve for a term expiring at the Annual Meeting, and one of our current Class II directors has been nominated to stand for re-election at the Annual Meeting to serve until the annual meeting of stockholders to be held in 2026. The other Class II director nominee for election at the Annual Meeting does not currently serve on our Board. The director nominees for the Annual Meeting are set forth below:

Key: COB – Chairman of the Board; Chair – Committee Chairman

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CURRENT BOARD DIVERSITY

2022 CORPORATE GOVERNANCE PRACTICES

We believe that strong corporate governance is essential and supports the long-term success of our business. Our Board and its committees help set the tone for our company, and our management devotes time and attention to matters of corporate responsibility, including environmental, social and governance (or ESG) matters. Our NG&S Committee has primary oversight for our ethics and governance efforts. We strive to implement corporate governance policies and structures that reflect best practices, including:

2022 COMPENSATION PROGRAMS AND PRACTICES

At our 2022 annual meeting of stockholders, our company received strong support for our executive compensation programs, with 92% of votes cast approving, on an advisory basis, our executive compensation.

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In 2022, as in prior years, our Compensation Committee considered the results of the say-on-pay vote in its review of our compensation program and policies and determined to continue with a compensation program that we believe is thoughtful, consistent and aligns with the company’s business strategies. We generally strive to align pay with company performance and to link the majority of pay for executives to long-term business strategies and key priorities. We measure incentive performance against challenging goals that are aligned with our key business priorities. We discourage imprudent risk taking by avoiding undue emphasis on any one metric or short-term goal.

Certain other key features of our executive compensation program include:

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DIAMOND OFFSHORE DRILLING, INC.

PROXY STATEMENT

For the Annual Meeting of Stockholders

to be held on May 10, 2023

QUESTIONS AND ANSWERS ABOUT THE ANNUAL MEETING AND VOTING

Why am I receiving these materials, and when and where will the meeting be held?

Our Board is providing you these proxy materials in connection with the Board’s solicitation of proxies for our Annual Meeting to be held at the office of the company located at 15415 Katy Freeway, Houston, Texas 77094, on Wednesday, May 10, 2023, commencing at 8:30 a.m. local time, and any adjournments and postponements of the Annual Meeting. This proxy statement summarizes information related to your vote at the Annual Meeting.

We intend to begin mailing proxy materials on or about March 30, 2023. Whether or not you plan to attend the Annual Meeting, you may submit a proxy to vote your shares by the Internet, phone or mail as described below.

If it is not possible or advisable to hold the Annual Meeting in person as planned, we will announce alternative arrangements for the meeting as promptly as practicable, which may include holding the Annual Meeting solely by means of remote communication. Any such change, including details on how to participate and vote in a remote Annual Meeting, would be announced in advance, and details would be posted on our website at www.diamondoffshore.com and filed with the Securities and Exchange Commission (or the SEC). It is important that you retain a copy of your Control Number found on the proxy card or voting instruction form, as such number will be required to gain access to any remote Annual Meeting. As always, we encourage you to vote your shares prior to the Annual Meeting.

What is the purpose of the Annual Meeting, and how does the Board of Directors recommend that I vote?

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Who is soliciting my proxy?

Our Board is soliciting proxies on our behalf using the enclosed proxy card to be voted at the Annual Meeting. All costs of soliciting the proxies will be paid by the company. Copies of solicitation materials will be furnished to banks, brokers, nominees and other fiduciaries and custodians to forward to beneficial owners of our common stock held by such persons. We will reimburse such persons for their reasonable out-of-pocket expenses in forwarding solicitation materials. In addition to solicitations by mail, some of the company’s directors, officers and other employees, without extra compensation, might supplement this solicitation by telephone, personal conversation or other communication.

Who is entitled to attend and vote at the Annual Meeting?

Only holders of record of our common stock at the close of business on March 14, 2023, the record date for the Annual Meeting (or the Record Date), or the holders of their valid proxies may attend and vote at the Annual Meeting. A list of our stockholders will be available for review at our executive offices in Houston, Texas during ordinary business hours for a period of 10 days prior to the meeting. Each person attending the Annual Meeting may be asked to present a photo ID before being admitted to the meeting. In addition, stockholders who hold their shares through a broker or nominee (i.e., in street name) should be prepared to provide proof of their beneficial ownership, such as a brokerage statement showing their ownership of shares as of March 14, 2023.

Each stockholder is entitled to one vote for each share of common stock held. Shares of our common stock represented in person or by a properly submitted proxy will be voted at the Annual Meeting. At the close of business on the Record Date, there were 101,416,965 shares of our common stock outstanding and entitled to vote. Common stock is our only class of stock entitled to vote at the Annual Meeting.

What constitutes a quorum?

The presence at the Annual Meeting, whether in person or by proxy, of the holders of a majority of the outstanding shares of our common stock entitled to vote at the Annual Meeting is required to constitute a quorum for the transaction of business.

How do I vote?

Stockholders of Record: Shares Registered in Your Name

If you are a stockholder of record, there are several ways for you to vote your shares. Whether or not you plan to attend the Annual Meeting, we urge you to vote by the enclosed proxy card prior to the Annual Meeting to ensure that your vote is counted.

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Beneficial Owners: Shares Registered in the Name of a Broker, Bank or Other Agent

If you are a beneficial owner of shares registered in the name of your broker, bank or other agent, you should have received a proxy card and voting instructions with proxy materials from that organization rather than directly from us. Please check with your bank, broker or other agent and follow the voting instructions they provide to vote your shares. Generally, you will have three options for returning your proxy.

If you receive multiple proxy cards from the company or your broker, bank or other agent, this usually indicates that your shares are held in more than one account, such as two brokerage accounts and are registered in different names. You should complete and return each of the proxy cards to ensure that all of your shares are voted. Unless you revoke your proxy, your shares of common stock represented by your proxy will be voted at the Annual Meeting in accordance with the directions given in your proxy.

How will my shares be voted if I do not specify how they should be voted?

If you are a stockholder of record and you indicate when voting in person, on the Internet or by telephone that you wish to vote as recommended by the Board, then your shares will be voted at the Annual Meeting in accordance with the Board’s recommendation on all matters presented for a vote at the Annual Meeting. Similarly, if you sign and return the enclosed proxy card but do not indicate how you want to vote your shares for a particular proposal or for all proposals, then for any proposal for which you do not so indicate, your shares will be voted in accordance with the Board’s recommendation.

If you are a beneficial owner of shares held in street name and do not provide the organization that holds your shares with specific voting instructions, then the organization that holds your shares may generally vote your shares in its discretion on “routine” matters but cannot vote on “non-routine” matters. If the organization that holds your shares does not receive instructions from you on how to vote your shares on a non-routine matter, that organization will inform the Inspector of Election that it does not have the authority to vote on that matter with respect to your shares. This is generally referred to as a “broker non-vote.”

If any other matter is presented at the Annual Meeting, your proxy will vote in accordance with his or her best judgment. As of the date of this proxy statement, we know of no matters that need to be acted on at the Annual Meeting other than those discussed in this proxy statement.

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Can I change my vote after I return my proxy card?

Your proxy may be revoked at any time before its exercise by signing, dating and delivering written notice of revocation to David L. Roland, Corporate Secretary, Diamond Offshore, 15415 Katy Freeway, Suite 100, Houston, Texas 77094, or by submitting a valid proxy that is dated later, or, if you attend the Annual Meeting in person, by submitting notice of revocation to the Inspector of Election referred to below during the Annual Meeting.

How will votes be recorded and where can I find the voting results of the Annual Meeting?

Votes will be tabulated and certified by our Inspector of Election. In tabulating votes, the Inspector of Election will make a record of the number of shares voted for or against each nominee and each other matter voted upon, the number of shares abstaining with respect to each nominee or other matter, and the number of shares held of record by broker-dealers that are present at the Annual Meeting but not voting. We plan to announce preliminary voting results during the Annual Meeting and to publish the final results in a current report on Form 8-K following the Annual Meeting.

What vote is required to approve each item to be voted on at the Annual Meeting?

Election of Directors. A plurality of the votes cast is required for the election of directors. Accordingly, the two valid nominees for election as Class II directors at the Annual Meeting who receive the most “For” votes among votes properly cast for election will be elected.

Frequency of Future Advisory Votes on Executive Compensation. For the advisory vote on the frequency of future advisory votes on executive compensation (Proposal No. 3), the option of every one year, every two years or every three years that receives the highest number of votes cast will be the recommendation of the stockholders considered by the Board.

Declassification of Board. The affirmative vote of the holders of at least 2/3 of the shares of common stock issued and outstanding as of the Record Date is required to approve the amendments to our Certificate of Incorporation to declassify the Board (Proposal No. 5).

Votes Required to Adopt Other Proposals. The affirmative vote of shares of common stock representing a majority of the votes cast (excluding abstentions and broker non-votes) by the holders of shares present and entitled to vote on the matter is required to approve each of the other proposals to be voted on at the Annual Meeting.

How are abstentions and broker non-votes counted?

Abstentions and broker non-votes (i.e., shares with respect to which a broker indicates that it does not have authority to vote on a matter) will be counted for purposes of determining whether a quorum is present at the Annual Meeting. Abstentions and broker non-votes will have the same effect as a vote “against” the proposal to amend our Certificate of Incorporation to declassify the Board. Shares that are voted to abstain and broker non-votes will not be counted as votes cast and, therefore, will have no effect on the outcome of the voting for directors or the outcome of the voting for any other proposal.

Conduct of the Meeting

The Chairman has broad responsibility and legal authority to conduct the Annual Meeting in an orderly and timely manner. This authority includes establishing rules of conduct and procedures for stockholders who wish to attend the meeting. In fairness to all stockholders in attendance, and in the interest of conducting a fair,

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informative, orderly and constructive meeting, the rules must be followed and will be enforced. Copies of the rules will be available at the Annual Meeting. Below are some of the rules that will apply:

Submitting a Question for the Annual Meeting

After the formal business of the Annual Meeting, as time allows, we will address properly-submitted questions from stockholders regarding the company. Stockholders who desire to submit a question for the Annual Meeting must submit the question by email to ir@dodi.com prior to the Annual Meeting, identifying their name and organization. Only questions submitted and received prior to the Annual Meeting will be addressed during the meeting. Questions from multiple stockholders on the same topic or that are otherwise related may be grouped, summarized and answered together. We will not address any questions that are not appropriate or relevant for the Annual Meeting, which could include, among other things, questions that we determine are:

If a stockholder has questions that are not answered during the meeting, the stockholder can contact the company’s Investor Relations Department at (281) 647-4035 or ir@dodi.com after the Annual Meeting.

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STOCK OWNERSHIP OF PRINCIPAL STOCKHOLDERS

The following table shows certain information as of March 1, 2023 as to all persons who, to our knowledge, were the beneficial owners of 5% or more of our common stock, which was our only outstanding class of voting securities as of such date. The information provided below with respect to the stockholders has been furnished to us by or on behalf of the stockholders, and we have not sought to independently verify such information. All shares reported were owned beneficially by the persons indicated unless otherwise indicated below.

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STOCK OWNERSHIP OF MANAGEMENT AND DIRECTORS

The following table shows the shares of our common stock beneficially owned as of March 1, 2023 by each of our current directors and director nominees, each of our executive officers named in the 2022 Summary Compensation Table below, and all our current directors and executive officers as a group. Each such director, nominee and executive officer individually, and all of our current directors and executive officers as a group, owned less than 1% of our common stock. Except as otherwise noted, the named beneficial owner had sole voting power and sole investment power with respect to the number of shares shown below.

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ELECTION OF DIRECTORS

(Proposal No. 1)

Overview of Changes to our Board of Directors and Corporate Governance Structure since 2021

On April 26, 2020, we and 14 of our subsidiaries filed voluntary petitions for reorganization under chapter 11 of the United States Bankruptcy Code in the United States Bankruptcy Court for the Southern District of Texas (or the Bankruptcy Court). On April 8, 2021, the Bankruptcy Court entered a written order in our chapter 11 reorganization confirming our Joint Plan of Reorganization (or our Joint Plan), and on April 23, 2021, our Joint Plan became effective and we emerged from bankruptcy. Effective upon our emergence, all of our existing directors resigned from the Board and all Board committees and the following six directors designated by our Ad Hoc Group of Senior Noteholders (as defined in our Joint Plan) were appointed to our Board: Neal P. Goldman, John H. Hollowell, Raj V. Iyer, Ane Launy, Patrick Carey Lowe and Adam C. Peakes.

In addition, effective upon our emergence in April 2021, our Certificate of Incorporation and Bylaws were amended to, among other things, classify our Board into three classes, designated as Class I, Class II and Class III, with one class of directors standing for election each year. The initial Class I directors served for an initial term that expired at our 2022 annual meeting of stockholders and, following the recommendation of our NG&S Committee, each of the initial Class I directors was nominated to stand for re-election as a Class I director at the 2022 annual meeting and was re-elected to serve until the annual meeting of stockholders to be held in the third year following the year of their election. The initial Class II directors serve for a term expiring at the Annual Meeting; and the initial Class III directors serve for a term expiring at the first annual meeting of stockholders following the Annual Meeting. Commencing with the Class I directors re-elected at our 2022 annual meeting, the successors of the class of directors whose term expires at each annual meeting shall be elected to hold office for a term expiring at the annual meeting of stockholders held in the third year following the year of their election and until each respective director’s successor is duly elected and qualified or his or her earlier death, resignation, disqualification or removal.

Effective on May 7, 2021, Bernie Wolford, Jr. was appointed as our President and CEO. On May 8, 2021, Mr. Wolford was appointed as a Class III member of our Board. In April 2022, our Board approved the addition of Benjamin C. Duster, IV to serve as a Class III director, effective on May 3, 2022. Our Board currently consists of the following directors:

Upon the recommendation of the NG&S Committee, the Board adopted, subject to stockholder approval at the Annual Meeting, amendments to our Certificate of Incorporation to declassify the Board and institute annual elections of directors on a phased-in basis. See “Approval of Amendments to our Certificate of Incorporation to Declassify our Board (Proposal No. 5).”

Director Nominees

Our Board currently consists of eight directors. One of our current directors, Ane Launy, was not nominated for re-election at the Annual Meeting. Following the recommendation of our NG&S Committee, the

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Board has nominated Patrice Douglas and Neal P. Goldman to stand for election as Class II directors at the Annual Meeting, to serve until the annual meeting of stockholders held in the third year following the year of their election or until each respective director’s successor is duly elected and qualified or his or her earlier death, resignation, disqualification or removal. Our Board has determined that each of such nominees (and each other member of the Board other than Mr. Wolford) satisfies the independence requirements provided for under the rules of the SEC and the New York Stock Exchange (or NYSE). The biographies of the nominees and our other continuing directors, including their business experience during the past five years and other background information and individual qualifications, attributes and skills, are described below.

The Board recommends a vote FOR the election of Patrice Douglas and Neal P. Goldman as Class II directors.

In the absence of contrary instructions, the proxies we receive from holders of our common stock will be voted at the Annual Meeting for the election of each of the Board’s nominees. Although we do not contemplate that either of the nominees will be unable to serve, decline to serve or otherwise be unavailable as a nominee at the time of the Annual Meeting, if that occurs we expect that the proxies will be voted for such other candidate(s) as our Board may nominate or our Board may adopt a resolution reducing the number of directors constituting our entire Board.

Class II Director Nominees for Election

Patrice Douglas, age 60, is an attorney representing energy companies, financial institutions, municipalities and utilities on legal, regulatory and compliance matters. From 2011 to 2015, Ms. Douglas served on the Oklahoma Corporation Commission (or the OCC), which regulates all oil and gas drilling, utilities and telephone companies in the state, including as Chairman of the OCC beginning in 2012. She served as Executive Vice-President of First Fidelity Bank from 2008 to 2011, and as Senior Vice-President and then President of SpiritBank from 2004 to 2008. Ms. Douglas also served as Mayor of Edmond, Oklahoma from 2009 through 2011. Ms. Douglas has served as a member of the board of directors, Chair of the Nominating and Governance Committee and a member of the Audit Committee of Amplify Energy Corp., a NYSE-listed independent oil and gas company, since February 2021, and as a member of the board of directors of Midstates Petroleum Company, Inc., an oil and gas company and predecessor to Amplify Energy, from 2016 through 2019, where she also served as Chair of the Nominating and Governance Committee and then Chair of the Audit Committee.

Ms. Douglas is a senior financial and legal executive with extensive experience in energy and a broad range of other industries. Her unique professional and leadership abilities, including as a director and audit committee member, will provide our Board with valuable strategic and analytical insight.

Neal P. Goldman has served as our Chairman of the Board since May 2021 and is currently the Managing Member of SAGE Capital Investments, LLC, a consulting firm specializing in independent board of director services, restructuring, strategic planning and transformations for companies in multiple industries including energy, technology, media, retail, gaming and industrials. Mr. Goldman was a Managing Director at Och Ziff Capital Management, L.P. from 2014 to 2016 and a Founding Partner of Brigade Capital Management, LLC from 2007 to 2012, which he helped build to over $12 billion in assets under management. Mr. Goldman has served on the board of directors as Chairman of the Board of Talos Energy Inc., a NYSE-listed oil and gas company, since 2018, and as a director, Chair of the Nominating and Governance Committee and a member of the Audit and Compensation and Human Resources Committees of Weatherford International plc, a publicly-traded oilfield services company, since 2019.

Mr. Goldman has over 25 years of experience in investing and working with companies in a variety of industries to maximize stockholder value. In addition to his current board of director service, Mr. Goldman has served on numerous other public and private company boards throughout his career, including Fairway Markets, Eddie Bauer, Toys R Us, J. Crew, Ultra Petroleum, Ditech Holding, Midstates Petroleum and

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NII Holdings. Through his extensive board of director experience, Mr. Goldman has developed expertise overseeing public and private companies that have experienced complex corporate governance and financial situations, which enables him to provide us and our Board with strategic direction and operational oversight.

Class III Incumbent Directors

Benjamin C. Duster, IV, is Founder and CEO of Cormorant IV Corporation, LLC, a consulting firm specializing in operational turnarounds and organizational transformations. Since June 2022, Mr. Duster has also served as Chief Financial Officer of Mobile Technologies, Inc., an electronics and loss prevention company, where he is responsible for the Finance/Accounting, HR, IT and Administrative functions. Prior to founding Cormorant in 2014, Mr. Duster was a Senior Adviser at Watermark Advisors from 2006 to 2015, Partner at Masson & Company from 2001 to 2006, a Managing Director at Wells Fargo (Wachovia Securities) from 1997 to 2001 and a Vice President at Salomon Brothers Inc. from 1985 to 1997. Mr. Duster has served as a director, Chair of the Audit Committee and member of the Strategic Review Committee of Republic First Bancorp, Inc., a publicly-traded commercial bank, since July 2022, as a director, Chair of the Audit Committee and member of the Compensation Committee of Chesapeake Energy Corporation, a publicly-traded oil and gas producer, since February 2021, and as a director, Chair of the Compensation and Human Resources Committee and a member of the Audit and Nominating and Governance Committees of Weatherford International plc, a publicly-traded oilfield services company, since 2020.

Mr. Duster is an experienced professional with particular focus on operations, finance and strategic advisory and interim management, helping organizations assess and improve their execution effectiveness to ensure long-term sustainable value creation. His extensive experience on Wall Street, including in mergers and acquisitions and strategic advisory services in developed and emerging markets, provides our Board with valuable expertise and vision.

Raj V. Iyer is the CEO and a director of SpecifX, Inc., a company focusing on direct lithium extraction. Prior to joining SpecifX in October 2022, Mr. Iyer served as a Partner and Senior Portfolio Manager at Canyon Partners, a leading alternative investment manager with approximately $25 billion in assets under management, from 2006 to April 2021. Prior to joining Canyon, Mr. Iyer worked as a managing director at Colden Capital Management. Mr. Iyer began his career at Morgan Stanley, where he worked on structuring derivative transactions. Mr. Iyer is a Chartered Financial Analyst.

Mr. Iyer is a senior investment professional with over 20 years of investment experience in complex restructurings and distressed debt in a variety of companies in energy, retail, financial services and other cyclical sectors. He has been deeply involved in the restructuring of the offshore services sector and has significant expertise in assessing balance sheet flexibility, optimizing cost of capital across financing sources and driving value-added returns for all stakeholders through governance and incentive alignment. This experience, combined with his financial and transactional expertise, enables Mr. Iyer to provide effective insight for our Board.

Bernie Wolford, Jr. has served as our President and CEO and as a director since May 2021. Prior to joining our company, Mr. Wolford served as the CEO and a director of Pacific Drilling S.A., a publicly-traded offshore drilling contractor, from November 2018 to April 2021. From 2010 to 2018, Mr. Wolford served in senior operational roles at Noble Corporation, another offshore drilling contractor, including five years as the company’s Senior Vice President – Operations. He began his career with Transworld Drilling Company in 1981 and has worked in numerous locations across the globe. Mr. Wolford is also a significant stockholder of Mass Technology Corporation, an independent service provider to the downstream refining and storage sector.

Mr. Wolford developed an extensive background in the global offshore drilling industry during his tenures at Pacific Drilling, Noble and Transworld that enables him to provide valuable contributions and perspective to our Board. His broad experience and understanding of the worldwide energy services industry provides valuable

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insight to our Board’s strategic and other deliberations. In addition, Mr. Wolford’s day-to-day leadership and involvement as our President and CEO provides him with personal direct knowledge and insight regarding our operations.

Class I Incumbent Directors

John H. Hollowell retired from Royal Dutch Shell in 2018, where he most recently served as the President and CEO of Shell Midstream Partners, L.P., a NYSE-listed company that owns, operates, develops and acquires pipelines and other midstream and logistics assets. Mr. Hollowell held numerous positions of increasing responsibility during his 38-year career with Shell, including serving as the Executive Vice President – Deepwater, responsible for Shell’s upstream business in the Gulf of Mexico and Brazil, Vice President – Production for Shell E&P Europe, where he was accountable for Shell’s offshore assets in the United Kingdom, Holland and Norway, and Vice President – Distribution for Shell’s downstream business, responsible for Shell’s fuel storage and distribution business globally. Since 2018, Mr. Hollowell has served on the board of managers for Beacon Offshore Energy, a privately-held independent E&P operator focused on deepwater Gulf of Mexico.

Mr. Hollowell’s extensive background in the global oil and gas industry while at Shell enables him to provide valuable advice to our Board on industry issues and customer perspectives. His broad experience and understanding of the worldwide energy services industry, including offshore exploration, provides additional insight for our Board.

Patrick Carey Lowe retired as the Executive Vice President and Chief Operating Officer at Valaris plc, a NYSE-listed offshore drilling contractor, in December 2019. Mr. Lowe served as Ensco’s Executive Vice President and Chief Operating Officer from 2015 until 2019, when Ensco merged with Rowan and the combined company was renamed Valaris. Mr. Lowe held numerous executive positions at Ensco, including Executive Vice President for investor relations, strategy and human resources; Senior Vice President of the eastern hemisphere; and Senior Vice President of engineering, capital projects and health, safety and the environment. Prior to joining Ensco, Mr. Lowe spent nearly 30 years in operational, engineering, human resources, and general management positions in the oil and gas industry, including general manager and hemisphere manager positions at Occidental Petroleum in Qatar and Latin America. Mr. Lowe began his career with Sedco, a U.S. drilling contractor that later became Sedco Forex under Schlumberger’s ownership. Since January 2020, Mr. Lowe has served on the board of directors and compensation committee of PHI Group, Inc., a provider of helicopter services for the oil and gas and aeromedical industries.

Mr. Lowe’s 40-year career in the oil and gas industry and as a former offshore drilling executive enables him to advise our Board on industry issues and perspectives. As a result of his extensive experience in oil and gas executive, corporate development and operational matters, Mr. Lowe provides the Board with expertise in industry corporate leadership, corporate planning and strategic development.

Adam C. Peakes has served as the Executive Vice President and Chief Financial Officer for the Hornblower Group, a privately-held company in the global travel and experiences industry, since April 2022. From 2019 through April 2022, Mr. Peakes was the Executive Vice President and Chief Financial Officer for Merichem Corporation, a privately-held company focused on sulfur removal and spent caustic handling for companies in the midstream and downstream energy sectors. Prior to joining Merichem, Mr. Peakes served as the Senior Vice President and Chief Financial Officer of Noble Corporation, a NYSE-listed offshore drilling contractor, from 2017 to 2019. From 2011 to 2016, Mr. Peakes was a Managing Director and Head of Oilfield Services at Tudor, Pickering, Holt & Company, an investment banking firm. Mr. Peakes served on the board of directors of Trecora Resources, a NYSE-listed manufacturer of specialty petrochemical products and provider of custom processing services, from 2019 to June 2022, and on the board of directors of Petroserv Marine Inc., an offshore drilling contractor with operations in Brazil, Indonesia and India, from 2020 to March 2021.

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Mr. Peakes’ background as a chief financial officer and his experience in the oilfield services financial sector provides him the necessary skills to lead our Audit Committee. His extensive experience in financial leadership and services, strategic financial management and investment banking enables him to provide our Board with valuable insight and expertise. This experience and knowledge also qualify him to serve as the financial expert on our Audit Committee.

Director Independence

In determining independence, each year our Board determines whether directors have any “material relationship” with our company or with any members of our senior management. When assessing the materiality of a director’s relationship with us, the Board considers all relevant facts and circumstances known to it and the frequency or regularity of the services provided to us or our affiliates by the director, any member of his or her immediate family, or any organizations with which the director has an affiliation, whether the services are being carried out at arm’s length in the ordinary course of business and whether the services are being provided substantially on the same terms to us as those prevailing at the time from unrelated parties for comparable transactions.

The Board has established guidelines to assist it in determining director independence. Under these guidelines, a director would not be considered independent if:

After considering all known relevant facts and circumstances and applying the independence guidelines described above, our Board has determined that each of our Class II director nominees and our current directors other than Mr. Wolford are independent under the NYSE’s corporate governance listing standards (or the NYSE Listing Standards) and our independence guidelines described above. We refer to our current seven independent directors as our Independent Directors.

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Board Committees

Our Board has established the following standing committees: Audit Committee, Compensation Committee and NG&S Committee. The current members of these standing Board committees are identified below:

From time to time, our Board also forms additional committees for specific purposes and limited durations. For example, in 2021, the Board appointed the Special Committee to explore strategic alternatives to maximize stockholder value. The Special Committee is comprised of Adam C. Peakes (Chair), Neal P. Goldman, John H. Hollowell and Patrick Carey Lowe.

Our Audit, Compensation and NG&S Committees operate under written charters that describe the functions and responsibilities of each committee. Each charter can be viewed on our website at www.diamondoffshore.com in the “Investors” section under “Corporate Governance.” A copy of each charter can also be obtained by writing to us at Diamond Offshore, Attention: Corporate Secretary, 15415 Katy Freeway, Suite 100, Houston, Texas 77094. The preceding Internet address and all other Internet addresses referenced in this proxy statement are for information purposes only and are not intended to be a hyperlink. Accordingly, no information found or provided at such Internet addresses or at our website in general (or at other websites linked to our website) is intended or deemed to be incorporated by reference in this proxy statement.

Audit Committee

The primary function of the Audit Committee is to assist our Board with its responsibility of overseeing the integrity of our financial statements, our compliance with legal and regulatory requirements, the qualifications and independence of our independent auditor, the performance of our internal audit function and independent auditor and our systems of disclosure controls and procedures, internal control over financial reporting and compliance with our adopted ethical standards. Our internal audit controls function maintains critical oversight over the key areas of our business and financial processes and controls, and provides reports directly to the Audit Committee. The committee has sole authority to directly appoint, retain, compensate, evaluate and terminate the independent auditor and to approve all engagement fees and terms for the independent auditor. The members of the committee meet regularly with representatives of our independent auditor firm and with our manager of internal audit without the presence of management.

Our Board has determined that each member of the Audit Committee satisfies the independence and other requirements for Audit Committee members provided for under the rules of the SEC and the NYSE. The Board has also determined that Adam C. Peakes qualifies as an “audit committee financial expert” under SEC rules. The Board has designated that Ms. Douglas will serve as a member of the Audit Committee if she is elected as a Class II director at the Annual Meeting and has determined that she satisfies the independence and other requirements for Audit Committee members provided for under the rules of the SEC and the NYSE.

Compensation Committee

The primary function of the Compensation Committee is to assist our Board in discharging its responsibilities relating to compensation of our executive officers. The Compensation Committee determines

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and approves compensation for our executive officers and directors and administers our employee incentive compensation plans. In accordance with its charter, the committee may form and delegate authority to sub-committees consisting of one or more of its members when appropriate. The committee does not delegate to management any of its functions in setting executive compensation under its charter. The committee has authority to retain or obtain advice of outside legal counsel, compensation consultants or other advisors to assist in the evaluation of director, CEO or executive officer compensation, including responsibility for the appointment, compensation and oversight of any such advisor retained by the committee. In 2021 and 2022, the committee engaged Lyons, Benenson & Company Inc., a compensation consulting firm (which we refer to as LB&C), to review and provide advice to the committee regarding our executive and non-employee director compensation programs. During 2022, a representative of LB&C attended most Compensation Committee meetings. In connection with the firm’s engagement, the committee considered the independence of LB&C in light of SEC rules and the NYSE Listing Standards and concluded that the work of the firm would not raise any conflict of interest. Among the factors considered by the committee in determining the firm’s independence were the following:

The Compensation Committee completes a review of all elements of compensation at least annually. All compensation decisions with respect to executive officers other than our CEO are determined in discussion with, and frequently based in part upon the recommendation of, our CEO. The committee makes all determinations with respect to the compensation of our CEO, including establishing performance objectives and criteria related to the payment of his compensation, and determining the extent to which such objectives have been achieved. See “Compensation Discussion and Analysis” for more information about the responsibilities of the Compensation Committee and the role of management with respect to compensation matters.

Compensation Committee Interlocks and Insider Participation. The current members of the Compensation Committee are Neal P. Goldman, John H. Hollowell and Ane Launy. Our Board has determined that each member of the Compensation Committee is independent and satisfies the additional independence requirements for compensation committee members provided for under the rules of the SEC and NYSE. No member of the Compensation Committee is, or was during 2022, an officer or employee of our company. During 2022:

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NG&S Committee

The NG&S Committee assists the Board with its responsibility for oversight of the director nominations process and our corporate governance, including determining and recommending to the Board the criteria for selecting director nominees; identifying, evaluating and recommending candidates and nominees for the Board, including consideration of any director candidates recommended by stockholders; and developing and recommending to the Board director independence standards, succession plans for the CEO and corporate governance policies and practices. The duties of the committee also include overseeing ESG matters and reviewing and making recommendations to the Board on our company’s policies and performance in relation to sustainability-related matters, including health and safety, process safety, the environment, climate change, human rights and workplace policies, security and emergency management, charitable and philanthropic activities, public advocacy and political donations, culture, inclusion and diversity. Our Board has determined that each member of the committee satisfies the definition of “independent” as established under the NYSE Listing Standards.

Board Diversity and Director Nominating Process

Our Board recognizes the benefits of diversity throughout our company and the merits of achieving diversity. In identifying, evaluating and nominating individuals to serve as our directors, including those identified by stockholders, our Board does not have formal diversity requirements or rules. Rather, the Board believes that our company is best served by directors with a wide range of perspectives, professional experience, skills and other individual qualities and attributes. Our Board considers diversity broadly to include diversity of race, ethnicity and gender, as well as diversity of viewpoint, professional experience and individual characteristics, qualities and skills, resulting in the inclusion of naturally varying perspectives among the directors. Our Board also considers whether these capabilities and characteristics will enhance and complement the full Board so that, as a unit, the Board possesses the appropriate skills and experience to oversee our business, ensure consideration of a wide range of perspectives and serve the long-term interests of our stockholders.

More than 37% of the directors currently serving on our Board are either female or racially or ethnically diverse. Our current directors vary in age from 36 to 65. As described above under our director biographies, the current composition of our Board also reflects a variety of expertise, skills, experience and professional and personal backgrounds, including in the following areas:

Our NG&S Committee will, subject to the terms of our Certificate of Incorporation and Bylaws, review any candidates recommended by stockholders for positions on the Board. Our Bylaws provide that any stockholder entitled to vote at a meeting of stockholders who is a record owner at the time of giving notice and at the time of the meeting and who satisfies the other requirements and complies with the procedures specified in our Bylaws may nominate persons for election to the Board, subject to any conditions, restrictions, limitations and other requirements imposed by our Certificate of Incorporation or Bylaws. These procedures include a requirement that our Corporate Secretary receive timely written notice of the nomination, which, for our next annual meeting of stockholders, means that the nomination must be received no earlier than January 11, 2024, and not later than February 10, 2024, unless the date of the next annual meeting is more than 30 days before or more than 60 days after May 10, 2024. Any notice of nomination must be addressed to Diamond Offshore,

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15415 Katy Freeway, Suite 100, Houston, Texas 77094, Attention: Corporate Secretary, and must include, as to each Nominating Person (as defined in our Bylaws), in addition to any other information required by our Certificate of Incorporation or Bylaws:

Nominations of directors may also be made by our Board as otherwise provided in our Bylaws. In determining whether it will nominate a candidate for a position on our Board, the Board considers those matters it deems relevant, which may include the candidate’s integrity; business specialization; career achievements; breadth of experience; soundness of judgment; ability to make independent analytical inquiries; independence and potential conflicts of interest; potential to meet the present needs of the Board in light of the current mix of director skills and attributes; ability to represent the total corporate interests of our company and our stockholders; and diversity of race, ethnicity and gender. While our Board believes that its current membership comprises a variety of perspectives, professional experience, skills and other qualities and attributes, the Board is committed to efforts to increase diversity and will continue to consider diversity of race, ethnicity and gender among other relevant factors when assessing individual candidates and nominees to fill Board vacancies that occur in the future.

Executive Sessions of Independent Directors

Our Independent Directors and each of the Audit Committee, Compensation Committee, and NG&S Committee meet regularly in executive sessions without the presence of management. Our Board has selected Neal P. Goldman to serve as the presiding director at meetings of our Independent Directors.

Board Leadership Structure

Our Board’s leadership structure consists of an independent Chairman of the Board and independent chairs of the Audit Committee, Compensation Committee and NG&S Committee. Neal P. Goldman currently serves as our Chairman of the Board. As an independent Chairman, Mr. Goldman also functions as the lead Independent Director by chairing separate meetings of the Independent Directors, facilitating the ability of the Independent Directors to fulfill their responsibilities and communicating any concerns of the Independent Directors to the full Board and to our executive management. The Board believes this structure provides

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independent Board leadership and engagement and strong oversight of management while providing the benefit of having the Chairman lead regular Board meetings as we discuss key business and strategic issues and set the agenda for Board meetings. Although our Board currently separates the roles of CEO and Chairman, our Board believes that either structure can be effective. Separating the roles of CEO and Chairman recognizes the differences between the two roles and allows our CEO to focus on our day-to-day business, while allowing our Chairman to guide the CEO and lead the Board in its fundamental role of providing advice to, and oversight of, management. Combining the CEO and Chairman roles can be beneficial because CEOs are closely involved in the day-to-day operations of their companies and are well positioned to elevate critical business issues for consideration by their boards of directors, and combining these positions would allow the CEO to effectively execute the company’s strategic initiatives and business plans and confront challenges facing the company. Our Board has no fixed policy with respect to combining or separating the positions and may in the future reevaluate this determination.

Board Oversight of Risk Management

Our Board recognizes the importance of understanding, evaluating and managing risk and its impact on the financial health of our company and has the ultimate oversight responsibility for the risk management process. The Board’s role in risk oversight is consistent with our leadership structure, with our CEO and other members of senior management having responsibility for assessing and managing our risk exposure, and the Board and its committees providing oversight in connection with those efforts. The Board exercises these responsibilities regularly as part of its meetings and also through the Board’s standing committees, each of which examines various components of enterprise risk as part of their responsibilities. In particular, the Audit Committee focuses on financial risk, including internal controls, and discusses risk assessment with management and our internal and external auditors. In addition, in setting compensation, the Compensation Committee endeavors to create incentives that encourage a level of risk-taking behavior consistent with our business strategies and long-term stockholder value. The NG&S Committee is specifically charged with overseeing ESG matters, including related risk management.

Our Board oversees an enterprise-wide approach to risk management, designed to support the achievement of organizational objectives, including strategic objectives, long-term organizational performance and enhanced stockholder value. The involvement of the full Board in setting our business strategy is a key part of the Board’s assessment of our tolerance for risk. The Board also regularly reviews information regarding our credit, liquidity and operations, as well as the associated risks, including cybersecurity risks. Throughout the year, the Board and the relevant Board committees receive updates from management with respect to various enterprise risk management issues and dedicate a portion of their meetings to reviewing and discussing specific risk topics in greater detail, including risks related to cybersecurity and COVID-19, to, among other things, assist in identifying the principal risks facing our company, identifying and evaluating policies and practices that promote a culture designed to appropriately balance risk and reward, and evaluating risk management practices.

Cybersecurity. Cybersecurity is a critical part of our risk management. To address cybersecurity threats more effectively, we leverage a multi-layered approach. We have a dedicated Chief Information Officer (or CIO) whose team is responsible for leading enterprise-wide information security strategy, policy, standards, architecture and processes. The Board and the Audit Committee receive regular updates from senior management, including the CIO, on matters such as major cyber risk areas, cybersecurity technologies and practices and cybersecurity incidents. We also periodically engage third parties to perform cybersecurity assessments to detect vulnerabilities, such as ransomware or data loss.

COVID-19. Since 2020, in addition to COVID-19 discussions as part of risk updates to the Board and the relevant Board committees, the Board has been provided with updates on COVID-19’s impact to our business, financial condition and operations through emails, teleconferences or other appropriate means of communication. We have COVID-19 risk protocols and responses embedded across our risk areas and will continue to evaluate our approach in addressing COVID-19-related risks as circumstances evolve.

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Director Attendance at Meetings

During 2022, our Board met six times, our Audit Committee met eight times, our Compensation Committee met eight times, our NG&S Committee met four times and our Special Committee met 20 times. Overall, the rate of attendance by our directors at Board and committee meetings during 2022 was 99%, and in 2022 no director attended less than 97% of the meetings of the Board and committees on which the director served. We do not require our Board members to attend our annual meeting of stockholders; however, five of our directors attended our 2022 annual meeting.

Director Compensation

Our Board has delegated to our Compensation Committee, which is comprised solely of independent directors, the primary responsibility for reviewing and considering revisions to our director compensation program. In setting director compensation, the committee considers the amount of time our directors expend in fulfilling their duties as well as the skill level required of members of our Board. The committee’s goal is to compensate our non-employee directors in a way that is competitive and attracts and retains directors of a high caliber. Mr. Wolford, our President and CEO, does not receive any cash or equity fee or other remuneration for his service as a director.

Upon our emergence from chapter 11 reorganization in April 2021, the Compensation Committee engaged LB&C to provide recommendations for our non-employee director compensation program. LB&C reviewed non-employee director compensation practices and trends and data from comparable oilfield services companies and recommended the following compensation program for our non-employee directors, which the Compensation Committee recommended to our Board and the Board approved, effective on April 23, 2021 (all cash retainer amounts to be paid in quarterly installments in advance):

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In addition, in August 2021, the company announced that the Board had established a special committee to explore strategic alternatives to maximize stockholder value. During 2022, the chair of the special committee was paid a monthly fee of $20,000, and the other members of the committee were each paid a monthly fee of $15,000.

In November 2022, based on advice and recommendations from LB&C, the Compensation Committee reevaluated the Board’s compensation program and approved grants of RSUs to non-employee directors for 2023 on January 18, 2023 with a grant date value of $120,000 (except our non-executive Chairman of the Board received a grant with a grant date value of $180,000). The 2023 RSUs will vest on the first anniversary of the grant date, subject to the director’s continuous service with our company through the vesting date. If a director resigns at our request for reasons other than cause, then 100% of the RSUs will immediately vest on the date of such termination. Upon a change in control of our company, 100% of the RSUs will vest, subject to the director’s continuous service through consummation of the change in control. We will issue and deliver to the director the number of shares equal to the number of vested RSUs following the earliest to occur of (x) the fifth anniversary of the grant date, (y) a separation from service, and (z) a change in control.

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Director Compensation for 2022

The following table summarizes the compensation earned by our non-employee directors in 2022:

As of December 31, 2022, these non-employee directors held the following outstanding, unvested company equity awards:

Code of Ethics and Corporate Governance Guidelines

We have a Code of Business Conduct and Ethics that applies to all of our directors, officers and employees, including our principal executive officer, principal financial officer and principal accounting officer. Our code can be found on our website at www.diamondoffshore.com in the “Investors” section under “Corporate Governance” and is available in print to any stockholder who requests a copy by writing to our Corporate Secretary. We intend to post any changes to or waivers of our code for our principal executive officer, principal financial officer and principal accounting officer on our website.

In addition, our Board has adopted written Corporate Governance Guidelines to assist our directors in fulfilling their responsibilities. The guidelines are on our website at www.diamondoffshore.com in the “Investors” section under “Corporate Governance” and are available in print to any stockholder who requests a copy from our Corporate Secretary.

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Environmental, Social and Governance (ESG) Focus

We are committed to conducting our business in a safe, environmentally responsible and sustainable manner, and in a way that reflects our responsibilities to our stakeholders, which includes our employees, customers, investors, business partners, regulators and citizens in the communities where we live and work. We also believe that the effective management of ESG issues will help support the sustainability and the long-term growth of our business, and create value for our stakeholders. Our NG&S Committee is responsible for reviewing and making recommendations to the Board on our policies and performance in relation to sustainability-related matters, including health and safety, process safety, the environment, climate change, human rights and workplace policies, security and emergency management, charitable and philanthropic activities, public advocacy and political donations, and culture, inclusion and diversity.

In 2021, under the oversight of our NG&S Committee, we began to develop our ESG strategy and establish a framework for monitoring our ESG initiatives. In January 2022, we published our 2021 Sustainability Report, which is posted on our website at www.diamondoffshore.com in the “Investors” section under “Corporate Governance.” The report describes our initial efforts and initiatives regarding sustainability, governance, the environment and our employees. We recognize we are in the early stages of our ESG journey, but also that our commitment can serve as the foundation for our global culture and help strengthen the ties between our success and the well-being of our employees, customers, stockholders, communities and other stakeholders. To further our goals, we have prioritized our work into the following key ESG objectives:

We understand the importance of being responsible stewards of our planet’s resources and the value in protecting it for our customers, communities and employees. We are in the beginning stages of developing our climate strategy but we have already made progress and have installed equipment on certain of our rigs to measure emissions, which has enabled us to identify methods for operating our rigs in a more fuel-efficient manner and thereby reduce greenhouse gas emissions and our carbon footprint.

We are committed to being a good corporate citizen as well as creating a positive employee environment. Our commitment to health and safety and the environment guides every aspect of our business. We pride ourselves on being an innovative leader in developing and implementing sophisticated and efficient job safety programs. We also believe that attracting, retaining and developing members of our workforce is critical to the sustainability of our business.

We invest in our people by recognizing the value of a diverse and inclusive workforce, offering numerous development and training opportunities, engaging employee programs, and providing generous benefit and wellness offerings. Creating and maintaining an environment where differences are valued and respected enhances our ability to recruit and retain the best talent in the marketplace and to provide a work environment that allows all employees to be their best.

We believe a healthy workforce leads to greater well-being at work and at home, and we offer benefits and resources to promote mental health and emotional wellness. Since the start of the COVID-19 pandemic in 2020, our management team has strived to promote the health and safety of our global employees. Throughout the pandemic, we have closely monitored the U.S. Centers for Disease Control and Prevention (CDC) and World Health Organization (WHO) guidelines to implement safety protocols for our employees in accordance with the latest guidance and provided services and resources to assist employees with a variety of medical and business needs.

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Conducting business the right way — with integrity, holding ourselves to high ethical standards and acting in compliance with applicable laws and regulations — is one of our core principles and a foundation for our operations. We emphasize a culture of accountability and conduct our business in a manner that is fair, ethical and responsible to earn the trust of our stakeholders, including customers, employees, communities, partners and regulators. We have adopted a culture of ethics, and our Code of Business Conduct and Ethics requires that our directors and employees make business decisions guided by compliance with applicable laws, rules and expectations for ethical conduct.

Loans to Directors and Executive Officers

We comply and operate in a manner consistent with regulations prohibiting loans to our directors and executive officers.

Prohibitions Against Hedging and Pledging

We have a policy that prohibits our directors and employees (including our executive officers) from engaging in any hedging or short sale transactions related to our stock or other equity securities, thereby preventing our directors, executives and other employees from insulating themselves from the effects of poor stock performance. We also have a policy that prohibits our directors and employees (including our executive officers) from pledging our stock or other securities as collateral for a loan.

Reporting of Ethics and Compliance Concerns

We have a dedicated hotline and website available to all employees to report ethics and compliance concerns, anonymously if preferred, including concerns related to accounting, accounting controls, financial reporting and auditing matters. The hotline and website are administered and monitored by an independent monitoring company. A description of our procedures for confidential anonymous complaints regarding accounting, internal accounting controls and auditing matters can be found on our website at www.diamondoffshore.com in the “Investors” section under “Corporate Governance—Confidential Reporting” and is available in print to any stockholder who requests a copy from our Corporate Secretary.

Public Policy Engagement and Political Activities

In recent years, we have not engaged in public policy or political activities, and as a policy we generally do not make corporate political contributions. We may on occasion contribute to elections and to state and local initiative or referendum campaigns where our interests are directly involved and where permitted by applicable law. Our company and some of our employees participate in industry and business trade groups that may engage in their own lobbying or other advocacy activities. In addition, we encourage our employees to exercise their voting rights and to take an active interest in the Federal, state and local elective processes.

Transactions with Related Persons

We have a written policy requiring that any transaction, regardless of the size or amount, involving us or any of our subsidiaries in which any of our directors, director nominees, executive officers, principal stockholders or any of their immediate family members has had or will have a direct or indirect material interest, be reviewed and approved or ratified by our Audit Committee. All such transactions must be submitted to our General Counsel for review and reported to our Audit Committee for its consideration. In each case, the Audit Committee will consider, in light of all of the facts and circumstances known to it that it deems relevant, whether the transaction is fair and reasonable to our company.

Pursuant to our Joint Plan, on April 23, 2021, we entered into a registration rights agreement with certain parties (or the RRA Stockholders) that became beneficial owners of 5% or more of our common stock upon our

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emergence from bankruptcy. The RRA Stockholders exercised their right to require us to file a shelf registration statement and we filed a registration statement on Form S-1, which we later converted to a registration statement on Form S-3, to register 20,229,065 shares of our common stock owned by the RRA Stockholders. The registration statement became effective on June 17, 2022. We will not receive any proceeds from the sale of these shares and will bear all expenses associated with the registration of such shares. The registration rights granted in the agreement are subject to customary indemnification and contribution provisions, as well as customary restrictions such as blackout periods.

On July 26, 2021, Avenue Energy Opportunities Fund II AIV, L.P. (or Avenue), a then-beneficial owner of more than 5% of our common stock, and Avenue’s investment manager, Avenue Capital Management II, L.P. (which we refer to collectively with Avenue as Avenue Capital), filed a complaint against us to compel an annual meeting of stockholders pursuant to 8 Del. C. Section 211(c) before the Court of Chancery of the State of Delaware. On August 31, 2021, we and Avenue Capital agreed to settle the complaint. Under the terms of the settlement, Avenue Capital agreed to dismiss the complaint with prejudice and release all claims with respect to the alleged failure by us or our directors and officers to hold our 2021 annual meeting of stockholders, and we agreed to hold our next annual meeting of stockholders no later than January 21, 2022. At the request of the parties, on September 1, 2021, the Court of Chancery ordered the action dismissed with prejudice.

We scheduled our 2022 annual meeting of stockholders to be held on January 21, 2022. On November 18, 2021, Avenue Capital delivered to the company a purported notice of nominations with respect to the election of Class I directors at the annual meeting. We notified Avenue Capital that the notice was invalid because the notice and Avenue did not comply with the requirements set forth in our Bylaws, and therefore the notice could not be accepted. On November 30, 2021, Avenue Capital filed a request with the Delaware court, seeking an order compelling us to accept their notice.

On December 29, 2021, we and Avenue Capital entered into an agreement providing for the settlement of the above disputes. Pursuant to the settlement agreement, Avenue Capital withdrew their nominations notice and Delaware court action. Under the terms of the settlement agreement, Avenue Capital agreed to customary standstill restrictions during the period from December 29, 2021 until the earlier of (x) the date 30 days prior to the deadline for the submission of stockholder nominations of director candidates for our 2023 annual meeting of stockholders and (y) any public announcement by us of an extraordinary transaction. During the above standstill period, Avenue Capital agreed to cause its common stock in our company to be present for quorum purposes at any meeting of our stockholders at which directors are elected and to vote in favor of the slate of directors nominated by our Board for election. In addition, we agreed that in the event a vacancy on our Board arises as a result of certain events occurring prior to the one-year anniversary of the settlement agreement, we will appoint one director designated by Avenue Capital to fill such vacancy.

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AUDIT COMMITTEE REPORT

As discussed above under the heading “Board Committees-Audit Committee,” a primary role of the Board’s Audit Committee is to oversee the company’s financial reporting process and manage its relationship with the independent auditor. In fulfilling its responsibilities, the Audit Committee has reviewed and discussed the company’s audited financial statements for the year ended December 31, 2022 with the company’s management and independent auditor. The Audit Committee has also discussed with the company’s independent auditor the matters required to be discussed by the applicable requirements of the Public Company Accounting Oversight Board and the SEC. In addition, the Audit Committee has discussed with the independent auditor its independence in relation to the company and its management, including the matters in the written disclosures provided to the Audit Committee as required by applicable requirements of the Public Company Accounting Oversight Board regarding the independent auditor’s communications with the Audit Committee concerning independence, and has determined that the provision of non-audit services provided by the auditor is compatible with maintaining the auditor’s independence.

The members of the Audit Committee rely without independent verification on the information provided to them by management and the independent auditor and on management’s representation that the company’s financial statements have been prepared with integrity and objectivity. The Audit Committee does not provide any expert or special assurance as to the company’s financial statements or any professional certification as to the independent auditor’s work. Accordingly, the Audit Committee’s oversight does not provide an independent basis to determine that management has applied appropriate accounting and financial reporting principles or internal controls and procedures, that the audit of the company’s financial statements has been carried out in accordance with generally accepted auditing standards, that the company’s financial statements are presented in accordance with generally accepted accounting principles, or that the company’s auditor is in fact “independent.”

Based on the review and discussions referred to above, the Audit Committee recommended to the Board of Directors that the audited financial statements be included in the company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2022, which has been filed with the SEC.

THE AUDIT COMMITTEE

Adam C. Peakes, Chair

Neal P. Goldman

Ane Launy

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COMPENSATION DISCUSSION AND ANALYSIS

Introductory note: The following discussion of executive compensation contains descriptions of various employee benefit plans and employment-related agreements. These descriptions are qualified in their entirety by reference to the full text or detailed descriptions of the plans and agreements, which are filed or incorporated by reference as exhibits to our Annual Report on Form 10-K for the year ended December 31, 2022 or a Current Report on Form 8-K subsequently filed with the SEC.

This Compensation Discussion and Analysis describes our executive compensation program for 2022 and explains how our Compensation Committee made its compensation decisions for 2022 for our executive officers identified in the following table, consisting of our CEO, our CFO and our other most highly compensated executive officers as of December 31, 2022. We refer to the below group of executive officers collectively as our “named executive officers” or “NEOs.”

Executive Summary

We successfully emerged from our chapter 11 reorganization in April 2021, so 2022 was our first full calendar year after our emergence. As a result, our incentive compensation programs in 2022 returned to being primarily performance-based, at risk and dependent upon our achievement of specific, measurable performance goals. Our Board approved a 2022 short-term incentive program (which we refer to as our 2022 Incentive Plan) that covered certain of our executives, including our NEOs. The 2022 Incentive Plan provided the executives the opportunity to earn cash compensation defined as a percentage of their base salaries that was at-risk and was contingent on achievement of certain specified performance metrics, in addition to applicable award caps. Performance under the 2022 Incentive Plan was measured from January 1, 2022 through December 31, 2022. After completion of the 2022 Incentive Plan performance period, our Compensation Committee determined that we achieved below target performance under the plan. As a result, payments under the 2022 Incentive Plan were paid below target. Details of the 2022 Incentive Plan results and payments are included below.

In July 2021, we granted performance-based RSU awards to certain of our key employees, including Messrs. Roland and Savarino, that vest based on the achievement of performance goals over three consecutive one-year performance periods. Upon the grant of the awards in July 2021, the Compensation Committee established the performance metrics and goals applicable to the first year performance period from July 1, 2021 through June 30, 2022 and provided that the metrics and goals for the two remaining subsequent one-year performance periods would be established each year by the Compensation Committee at the beginning of the applicable performance period. After the completion of the first year performance period in 2022, the Compensation Committee determined that the Company had achieved 88% of the first year performance goals and therefore 88% of the 2021 performance-based RSU awards held by Messrs. Roland and Savarino applicable to the first year performance period were vested.

In addition, in 2022 the Compensation Committee established the performance metrics and threshold, target and stretch performance goals applicable for the second year performance period, which is effective from July 1, 2022 through June 30, 2023, for the 2021 performance-based RSU awards originally granted to Messrs. Roland and Savarino. The performance goals for the second-year performance period consist of (i) a specified level of achievement of five health, safety and environmental objectives, (ii) a specified level of

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achievement of adjusted EBITDA, (iii) a specified amount of added cumulative contract backlog, (iv) a specified level of achievement of four ESG objectives and (v) achievement of strategic initiative goals determined by the Compensation Committee.

As approved by our Compensation Committee, on May 12, 2022, we granted additional equity incentive awards to certain of our key employees, including our CEO and other NEOs, consisting of time-based RSU awards that vest in equal amounts annually over a three-year period and performance-based RSU awards that vest based on the achievement of a target stock appreciation performance goal over a three-year period as determined by the Compensation Committee.

At our annual meeting of stockholders held in January 2022, our stockholders approved all our director nominees and proposals, including 92% approval of a non-binding advisory (say-on-pay) vote to approve the compensation of our executive officers. After our 2022 annual meeting, our Compensation Committee considered the results of the say-on-pay vote in its review of our compensation policies and has continuously re-evaluated and, as necessary, revised our compensation programs to make the programs more effective and responsive in achieving their intended reward, retention and incentive goals. We believe that we accomplished those goals during 2022.

Compensation Philosophy and Program Objectives

Through our executive compensation program, we seek to achieve the following general goals:

We do not rely on formula-driven plans when determining the aggregate amount of compensation for each NEO. The Compensation Committee takes many factors into account when making compensation decisions with respect to our executives, including the individual’s performance and experience; the ability of the individual to affect our long-term growth and success; the company’s overall performance; internal equity among the executives; and external, publicly available market data on competitive compensation practices and levels. The committee typically establishes the annual compensation program during the first quarter of each fiscal year, setting specific annual and long-term company goals and designing the compensation program for that year to support and reward the achievement of those goals. In setting the compensation for our NEOs other than the CEO, the committee considers, among other things, the recommendations of our CEO. Our CEO’s recommendations are reviewed with and are acted upon by the committee in accordance with its charter. At least once a year, the committee reviews the compensation of our CEO and considers any necessary adjustments to his compensation level. The Committee is solely responsible for making all decisions on the compensation of our executives, and no executive is involved in determining any element of his or her own compensation.

Market Considerations. When making compensation decisions, we have also compared the compensation of our executive officers to the compensation paid to executives of comparably-sized companies engaged in businesses similar to ours, although we do not benchmark our compensation to any particular group of companies. In comparing compensation, we have considered market data, executive compensation surveys, advice of compensation consultants and other information related to compensation levels and practices. We

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believe, however, that any such comparison should be merely a point of reference and not the determinative factor for our executives’ compensation. The purpose of the comparison is to inform, but not supplant, the analyses of internal pay equity and individual performance that we consider when making compensation decisions. Accordingly, the Compensation Committee has discretion in determining the nature and extent of its use of comparative compensation information.

When reviewing executive compensation, the Compensation Committee may also consider our company’s performance during the person’s tenure and the anticipated level of compensation that would be required to replace the person with someone of comparable experience and skill. In addition to our periodic compensation review, we also regularly monitor market conditions and may adjust compensation levels as necessary to remain competitive and retain valuable employees.

Elements of Compensation

In 2022, the principal components of compensation for our NEOs were:

Base Salary

Base salaries are established for each salaried position, including the positions held by our NEOs, after considering objective criteria relevant to the position, such as the position’s level of financial and operational responsibility and supervisory duties, as well as the education and skills required to perform the functions of the position, and subjective factors such as the employee’s contribution to our company and individual performance. The Compensation Committee recognizes that our CEO’s compensation should reflect his greater policy- and decision-making authority and higher level of responsibility with respect to our strategic direction and our financial and operating results. At December 31, 2022, our CEO’s annual base salary was approximately 59% higher than the annual base salary for the next highest-paid NEO and approximately 61% higher than the average annual base salary for our other NEOs.

The Compensation Committee reviews base salaries of our executives, including our NEOs, at least annually and may also adjust salaries from time to time to realign salaries with external market levels after considering individual responsibilities, performance and contribution to our company, experience, internal pay equity and budgetary issues.

The following table shows the annual base salaries for each of our NEOs as of January 1, 2022:

On May 7, 2021, we appointed Mr. Wolford as our President and CEO with an annual base salary of $700,000. In 2021, to reduce costs, our executives, including the NEOs, agreed to a voluntary temporary 5%

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reduction in base salary effective from August 16, 2021 through April 1, 2022. After considering market compensation information and receiving advice and recommendations from LB&C, effective August 1, 2022, the Compensation Committee approved a 5% increase in base salary for Mr. Wolford to $735,000, and a 6% increase in base salary for Mr. Roland to $430,000.

2022 Short-Term Incentive Program

In April 2022, our Compensation Committee approved our 2022 Incentive Plan, which covered certain of our executives, including our NEOs. The 2022 Incentive Plan provided the executives the opportunity to earn cash compensation that was at-risk and was contingent on achievement of certain specified performance metrics, in addition to applicable award caps. The plan’s target award levels were developed based on a combination of factors, including our compensation philosophy, market compensation data and the executive’s experience, leadership, prior contribution to the company’s success and individual performance. The plan was designed to reward executives for achieving certain performance goals that are important to the success of our company. Performance under the 2022 Incentive Plan was measured from January 1, 2022 through December 31, 2022.

Under the 2022 Incentive Plan, individual target awards were equal to a fixed percentage of base salary. The 2022 target awards for the Company’s NEOs are set forth below:

The Compensation Committee determined the following performance metrics for the 2022 Incentive Plan, each of which is weighted as set forth below:

Under the 2022 Incentive Plan, the payout based on the performance metrics was determined based on the level of achievement as determined by the Compensation Committee relative to the pre-established goals, expressed as a percentage of the 2022 cash incentive target amount specified above, according to the following table:

If performance fell between the designated points in the table above, the incentive payout amount would be determined by straight-line linear interpolation (except that no incentive is paid for performance below threshold).

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Under the 2022 Incentive Plan, the EBITDA performance goal is calculated as follows:

The Compensation Committee selected EBITDA as the primary performance metric under the 2022 Incentive Plan because the measure generally tracks our company’s financial performance and establishes a clear and consistent link between the company’s executive cash incentive compensation and the company’s performance. Consequently, for purposes of the 2022 Incentive Plan, the calculation of EBITDA excluded certain designated revenue, costs and expenses to remove the positive or negative impact of unusual or one-time events that would obscure the core operational performance of our company, including non-forecasted incentive compensation expenses, expenses associated with mergers, acquisitions or other strategic initiatives, if any, and revenue, costs and expenses incurred in connection with events or conditions determined in consultation with the Compensation Committee to be extraordinary or unusual in nature, infrequent in occurrence, out of our company’s control, or that negatively impacted EBITDA during the performance period for a future benefit outside of the performance period.

The 2022 EBITDA performance targets under the 2022 Incentive Plan were as follows (with straight-line linear interpolation applied between the points):

The 2022 HSE performance targets under the 2022 Incentive Plan were as follows (with straight-line linear interpolation applied between the points):

The 2022 strategic initiative target under the 2022 Incentive Plan was as follows:

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In February 2023, for purposes of consideration of 2022 Incentive Plan awards, the Compensation Committee reviewed the company’s financial and HSE performances and the company’s pursuit of strategic initiatives during the plan’s performance period, exercised its business judgment and determined that the NEOs achieved 85.4% of target performance under the plan. As a result, payments under the 2022 Incentive Plan were paid at 85.4% of target amounts, and our NEOs received the following payments pursuant to our 2022 Incentive Plan:

2021 Long-Term Incentive Awards

Award to CEO. In connection with his hire as our President and CEO in May 2021, the Compensation Committee approved two incentive awards to Mr. Wolford pursuant to the terms of our Stock Plan:

If Mr. Wolford’s employment is terminated by us without “cause” (as defined in our Stock Plan), due to his death or disability, or by Mr. Wolford for “good reason” (as defined in our Stock Plan), then the number of shares of restricted stock that would have otherwise vested pursuant to the CEO Time-Vesting Award in the 12-month period following such termination will immediately vest on the date of such termination, subject to the terms and conditions of the applicable award agreement. However, in the case of any such termination within the period starting six months prior to the occurrence of a “change in control” (as defined in our Stock Plan) and ending 12 months following the occurrence of a change in control, then in lieu of the benefits described in the preceding sentence, the restricted stock pursuant to the CEO Time-Vesting Award will fully vest immediately upon such termination of employment, subject to the terms and conditions of the applicable award agreement. If the CEO Time-Vesting Award is not continued, assumed, replaced, converted or substituted upon the occurrence of a change in control in accordance with our Stock Plan, then the restricted stock will fully vest as of immediately prior to a change in control.

If Mr. Wolford’s employment is terminated by us without cause, due to his death or disability, or by Mr. Wolford for good reason within the period starting six months prior to the occurrence of a change in control

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and ending 12 months following the occurrence of a change in control, then the restricted stock pursuant to the CEO Performance-Vesting Award will fully vest immediately upon such termination of employment, subject to the terms and conditions of the applicable award agreement.

Mr. Wolford receives all privileges of a stockholder of the company with respect to his shares of restricted stock, including the right to vote any shares underlying the restricted stock and to receive dividends or other distributions.

After reviewing relevant data regarding sales of company stock since May 2021, in July 2022 the Compensation Committee determined that the Performance Measurement Date applicable to the CEO Performance-Vesting Award had occurred. After calculating the company’s highest Total Equity Value from the May 2021 grant date through the Performance Measurement Date in accordance with his award agreement, the company determined that 493,847 shares of performance-vesting restricted stock granted to Mr. Wolford had vested on August 12, 2022. Subsequently, after calculating the company’s highest Total Equity Value from the Performance Measurement Date through December 30, 2022, the company determined that 253,560 additional shares of performance-vesting restricted stock granted to Mr. Wolford had vested as of December 30, 2022. As of December 31, 2022, Mr. Wolford continued to hold the remaining 30,370 unvested shares of performance-vesting restricted stock. Thereafter, on March 1, 2023, the company calculated its highest Total Equity Value since the Performance Measurement Date and determined that Mr. Wolford’s remaining 30,370 shares of performance-vesting restricted stock had vested as of March 1, 2023.

Awards to Other NEOs. As approved by the Compensation Committee, on September 1, 2021 we entered into award agreements for grants made as of July 1, 2021 of incentive awards under our Stock Plan to certain of our key employees, including Messrs. Savarino and Roland, consisting of time-based RSU awards that vest in equal amounts annually over a three-year period and performance-based RSU awards that vest in equal amounts annually over a three-year period subject to annual performance goals.

In addition to the RSU awards granted as of July 1, 2021, Mr. Savarino was granted additional time-based RSUs and performance-based RSUs on October 1, 2021 in connection with his promotion from Vice President and Chief Accounting & Tax Officer to Senior Vice President and Chief Financial Officer on September 20, 2021. The RSUs granted on October 1, 2021 are subject to the same vesting and other terms as his time-based and performance-based RSUs granted as of July 1, 2021.

The number of RSUs included in the July 1, 2021 and October 1, 2021 awards to the NEOs were as follows:

The time-based RSUs vest with respect to approximately 1/3 of the RSUs on each of July 1, 2022, July 1, 2023 and July 1, 2024, subject to the recipient’s continuous service or employment through the applicable vesting date. If the recipient is terminated without “cause” (as defined in our Stock Plan) or because of the recipient’s death or disability, then the number of time-based RSUs that would vest on the next two vesting dates will immediately vest on the date of such termination. Upon a termination for cause, all vested and unvested time-based RSUs will immediately be forfeited and cancelled for zero compensation. Upon a termination of service for any other reason, all outstanding and unvested time-based RSUs will immediately be forfeited and cancelled for zero compensation. Upon a “change in control” (as defined in our Stock Plan) of our company, the number of time-based RSUs that would vest on the next two vesting dates will immediately vest, subject to the recipient’s continuous service or employment through consummation of the change in control.

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The performance-based RSUs vest with respect to up to approximately 1/3 of the RSUs on each of June 30, 2022, June 30, 2023 and June 30, 2024, subject to the recipient’s continuous employment with our company through the applicable vesting date and the level of achievement of performance goals for each one-year performance period as determined by the Compensation Committee. For the first performance period from July 1, 2021 through June 30, 2022, the performance-based RSUs were subject to four equally-weighted performance goals, consisting of (i) five target HSE objectives, (ii) a target amount of adjusted free cash flow, (iii) a target amount of added cumulative contract backlog and (iv) achievement of strategic initiative goals determined by the Board. The Compensation Committee selected the HSE, financial and backlog performance metrics for the first year performance period because the metrics are considered primary drivers of value for offshore drilling companies and establish a clear and measurable link between the company’s executive long-term incentive compensation and the company’s performance.

The HSE, financial and backlog performance goals for the first performance period from July 1, 2021 through June 30, 2022, along with the results of the company’s actual performance during the performance period, were as follows (dollar amounts in millions):

In August 2022, for purposes of consideration of vesting of the performance-based RSUs applicable to the first year performance period ended June 30, 2022, the Compensation Committee reviewed the above performance period results, exercised its business judgment and determined that the NEOs achieved 88% of target performance. As a result, the performance-based RSUs applicable to the first year performance period vested at 88% of target, and Messrs. Savarino and Roland received the following vested RSUs (before tax withholdings):

The 2021 RSU performance goals for the second-year period from July 1, 2022 through June 30, 2023 of the performance period consist of (i) five target HSE objectives, (ii) a target amount of adjusted EBITDA, (iii) a target amount of added cumulative contract backlog, (iv) four target ESG objectives and (v) achievement of strategic initiative goals determined by the Board. The performance metrics and threshold, target and stretch performance goals applicable to the third-year performance period of the 2021 RSUs, which covers July 1, 2023 through June 30, 2024, will be established by the Compensation Committee in 2023.

Unless otherwise determined by the Compensation Committee, the percentage of the performance-vesting awards eligible to vest may range from 0% to 100% of the target amount, based on the specified levels of achievement of the applicable performance goals. In no event will the recipient be eligible to earn more than 100% of the target amount for any performance period. If the recipient is terminated without cause or because of the recipient’s death or disability, then the recipient will remain eligible to vest, subject to achievement of

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the performance conditions, in the number of performance-based RSUs that would vest on the next two vesting dates. Upon a termination for cause, all vested and unvested performance-based RSUs will immediately be forfeited and cancelled for zero compensation. Upon a termination of service for any other reason, all outstanding and unvested performance-based RSUs will immediately be forfeited and cancelled for zero compensation. Upon a change in control of our company, the number of performance-based RSUs that would vest on the next two vesting dates will immediately vest to the extent of the achievement of certain performance goals through the date of the change in control, or based on deemed achievement target performance for certain other performance goals.

The NEOs do not have any privileges of a stockholder of the company with respect to any RSUs, including any right to vote any shares underlying the RSUs or to receive dividends or other distributions; provided that, if the company declares any dividend while the RSUs are outstanding, the holder will be credited a dividend equivalent, which will be subject to the same vesting conditions applicable to the RSU and will vest only if the RSU vests and will be forfeited if the RSU is forfeited. Any such dividend equivalents will be settled and paid to the holder following the date on which the RSU vests. All RSUs may be settled in cash or our common stock.

2022 Long-Term Incentive Awards

As approved by the Compensation Committee, on May 12, 2022 we granted incentive awards under our Stock Plan to certain of our key employees, including our CEO and other NEOs, consisting of time-based RSU awards that vest in equal amounts annually over a three-year period and performance-based RSU awards that vest based on the achievement of a target stock appreciation performance goal over a three-year period. The number of RSUs included in the May 12, 2022 awards to our NEOs were as follows:

The time-based RSUs vest with respect to approximately 1/3 of the RSUs on each of May 12, 2023, May 12, 2024 and May 12, 2025, subject to the recipient’s continuous employment through the applicable vesting date. If the recipient is terminated for “cause” (as defined in the award agreement), all vested and unvested time-based RSUs will immediately be forfeited and cancelled for zero compensation. In connection with a “change in control” (as defined in the award agreement) in which the award is continued, assumed or replaced with an economically equivalent equity-based award that contains substantially comparable terms and conditions (or a Rollover Award), the Rollover Award will vest in accordance with the above vesting schedule. In the case of a Rollover Award, upon the occurrence of a termination of the recipient’s employment (i) by our company without cause, (ii) by the recipient for “good reason” (as defined in the award agreement) or (iii) by reason of the recipient’s death or disability during the 12-month period following such change in control, such award will 100% vest as of the date on which such termination occurred. In connection with a change in control in which the award does not become a Rollover Award, a pro-rated portion of the number of RSUs scheduled to vest on the next vesting date (to the extent not previously vested) will immediately vest in full, subject to the recipient’s continued service through the consummation of the change in control and, to the extent not continued, assumed or replaced in connection with the change in control, any remaining unvested time-based RSUs will immediately be forfeited and cancelled for zero compensation. Upon a termination of service for any other reason, all outstanding and unvested time-based RSUs will be forfeited and cancelled for zero compensation.

The performance-based RSUs vest based on the level of achievement of our stock price through May 12, 2025 (unless terminated earlier in connection with a “change in control” as defined in the award agreement), subject to the recipient’s continuous employment through the end of the performance period. On the May 12, 2022 grant date, the 30 consecutive trading day volume-weighted average price of our common stock, or

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30-day VWAP, was $7.34. If, at any time during the three-year performance period, the highest 30-day VWAP of our common stock equals $8.37, then 1/3 of the RSUs will vest. If, at any time during the three-year performance period, the highest 30-day VWAP of our common stock equals $9.55, then 2/3 of the RSUs will vest. If, at any time during the three-year performance period, the highest 30-day VWAP of our common stock equals or exceeds $10.87, then 100% of the RSUs will vest. If the highest 30-day VWAP of our common stock falls between any of the above thresholds, straight-line interpolation will be applied to determine the number of RSUs that will vest. If, at any time during the three-year performance period, the highest 30-day VWAP of our common stock does not reach $8.37, then none of the RSUs will vest, and the performance-based RSUs will be forfeited and cancelled for zero compensation. Vested time-based RSUs and performance-based RSUs may be settled by the company in cash in lieu of stock.

If the recipient is terminated for “cause” (as defined in the award agreement), all vested and unvested performance-based RSUs will be forfeited and cancelled for zero compensation. Upon the occurrence of a termination of the recipient’s employment (i) by our company without cause, (ii) by the recipient for “good reason” (as defined in the award agreement) or (iii) by reason of the recipient’s death or disability, the performance-based RSUs will vest as set forth above (without regard for the requirement that the recipient remain in continuous employment through the end of the performance period) based on the highest 30-day VWAP achieved during the performance period prior to the termination, and any unvested performance-based RSUs will immediately be forfeited and cancelled for zero compensation.

In connection with a change in control in which there is a Rollover Award of performance-based RSUs, the Rollover Award will vest based on the 30-day VWAP as set forth above (subject to equitable adjustable to account for such change in control). In the case of a Rollover Award, upon the occurrence of a termination of the recipient’s employment (i) by our company without cause, (ii) by the recipient for good reason or (iii) by reason of the recipient’s death or disability, during the 12-month period following the change in control, the performance-based RSUs will vest as follows:

Upon the occurrence of a change in control in which the performance-based RSU award does not become a Rollover Award, the award’s performance period will terminate upon the consummation of the change in control and the performance-based RSUs will vest upon the consummation of the change in control as follows:

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Personal Benefits, Perquisites and Employee Benefits

We do not offer many perquisites traditionally offered to executives of similarly-sized companies. Perquisites and any other similar personal benefits generally offered to our executive officers are substantially the same as those generally available on a non-discriminatory basis to all of our full-time salaried employees, such as medical and dental insurance, life insurance, disability insurance, a 401(k) plan with a company match and other customary employee benefits. We make contributions for group term life insurance, spouse/dependent life insurance, and long-term disability insurance for our employees, including our NEOs, as indicated in the 2022 Summary Compensation Table below. Business-related relocation benefits may be reimbursed on a case-by-case basis.

We maintain a defined contribution plan (which we refer to as our Retirement Plan) designed to qualify under Section 401(k) of the Internal Revenue Code of 1986, as amended (which, together with the regulations promulgated thereunder, we refer to as the Code). Pursuant to our Retirement Plan, in 2022 we matched 50% of the first 6% of each participant’s compensation contributed. Effective on January 1, 2023, we increased the company match to 100% of the first 4% of each participant’s compensation contributed. In addition, under our Amended and Restated Supplemental Executive Retirement Plan (which we refer to as our SERP), in past years we have contributed to participants any portion of the applicable percentage of the base salary contribution and the matching contribution that cannot be contributed under the Retirement Plan because of the limitations within the Code. Participants in this plan are a select group of our management or highly compensated employees, including our NEOs, and are fully vested in all amounts paid into the plan. As a result of our chapter 11 reorganization, we did not contribute any amounts into our SERP during 2020, 2021 or 2022. In October 2022, our Compensation Committee approved the resumption of contributions to our SERP for 2023.

Supplemental Severance Plan. On September 1, 2021, we issued the Diamond Offshore Drilling, Inc. Supplemental Severance Plan, effective as of September 21, 2021, for eight key employees, including Messrs. Savarino and Roland. The Supplemental Severance Plan provides the participants with protection for loss of salary and benefits in the event of certain involuntary terminations of employment in order to assist our company in retaining its senior management team.

The Supplemental Severance Plan provides that if an eligible participant’s employment is terminated by our company without “cause” or as a result of the recipient’s death or disability or a resignation for “good reason” (each of “cause” and “good reason” as defined in the Supplemental Severance Plan), the participant will be eligible to receive a lump-sum cash payment in an amount equal to the sum of the participant’s annual base salary and annual target bonus and, subject to the participant’s election of continuation of health care coverage pursuant to COBRA, we will pay the full cost of the participant’s COBRA premiums for 12 months from the date of the termination. If an eligible participant’s employment is terminated by our company without cause or due to a resignation for good reason within six months prior to, or one year following, a change in control of our company, the participant will instead be eligible to receive a lump-sum cash payment in an amount equal to 1.5 times the sum of the participant’s annual base salary and annual target bonus and, subject to the participant’s election of COBRA coverage, we will pay the full cost of the participant’s COBRA premiums for 18 months from the date of such termination. Receipt of severance benefits is subject to the participant’s execution of a release of any claims against our company and agreement with restrictive covenants, including a covenant of non-solicitation of customers and employees.

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Indemnification of Directors and Executive Officers

Our Certificate of Incorporation provides certain rights of indemnification to our directors and officers (including our executive officers) in connection with legal actions brought against them by reason of the fact that they are or were a director or officer of our company, to the fullest extent permitted by law. Our Certificate of Incorporation also eliminates the personal liability of our directors to our company or our stockholders for monetary damages for breach of fiduciary duty as a director to the fullest extent permitted by law. Our Certificate of Incorporation also provides that, to the fullest extent permitted by law, non-employee directors and their affiliates (other than our company, any of its subsidiaries or their respective officers or employees) shall not be liable to our company or our stockholders or to any affiliate of our company for breach of any fiduciary duty solely by reason of the fact that such non-employee director or affiliate (A) engaged in or possessed interests in other business ventures of any type or description, including those engaged in the same or similar business activities or lines of business in which our company or any of our subsidiaries now engages or proposes to engage, or (B) competed with our company or any of our subsidiaries, on its own account, or in partnership with, or as an employee, officer, director or stockholder of any other person (other than our company or any of our subsidiaries). In addition, except to the extent provided otherwise in our Certificate of Incorporation, to the fullest extent permitted by law, such persons shall not be liable to our company or our stockholders or to any of our subsidiaries for breach of any duty (fiduciary, contractual or otherwise) as a stockholder or director of our company by reason of the fact that such person does not present certain corporate opportunities to our company.

Our Bylaws contain provisions that provide for the indemnification of officers and directors as authorized by law, subject to certain terms and conditions set forth therein.

We have entered into indemnification agreements with each of our directors and executive officers that generally provide for us to indemnify the applicable indemnitee to the fullest extent permitted by applicable law (subject to certain limitations) as well as the advancement of all expenses incurred by the director or executive officer in connection with a legal proceeding arising out of their service to our company, in each case to the extent permitted by applicable law.

In addition, as authorized by our Bylaws, we have an existing directors’ and officers’ liability insurance policy.

Risk Management Considerations

Our Compensation Committee has concluded that our compensation program does not encourage excessive or inappropriate risk-taking. Several elements of our compensation program are designed to promote the creation of long-term value and thereby discourage behavior that leads to excessive risk:

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Employment Agreements

During 2022, we did not have employment agreements with any of our NEOs except for Bernie Wolford, Jr., our President and CEO. In connection with his hire as our President and CEO, on May 8, 2021 we entered into an employment agreement with Mr. Wolford, which has a term continuing until terminated by us or Mr. Wolford, or until his death or disability, in accordance with the employment agreement. Pursuant to the terms of the agreement, Mr. Wolford will receive an annualized base salary of at least $700,000 and will be eligible to earn a bonus with a target annual bonus opportunity equal to at least 100% of base salary, payment of which is based on the achievement of certain financial or individual performance goals and factors. Mr. Wolford is also entitled to participate in our benefit programs generally available to other senior officers and to receive reimbursement of certain expenses incurred during his employment.

If Mr. Wolford’s employment is terminated due to his death or by us due to his disability, he will be entitled to any accrued but unpaid annual bonus with respect to the preceding calendar year. If Mr. Wolford’s employment is terminated by us without “cause” (as defined in his agreement) or by Mr. Wolford with “good reason” (as defined in his agreement) in accordance with his employment agreement, he will be entitled to (i) any accrued but unpaid annual bonus with respect to the preceding calendar year, (ii) a lump-sum cash payment equal to 200% of the sum of (A) his base salary plus (B) target annual bonus and (iii) continued participation in our group health plan for him and his eligible dependents for a period of 24 months at our expense, in each case subject to the terms and conditions of his employment agreement. No severance is payable upon termination of employment for cause or a voluntary termination by Mr. Wolford without good reason.

Mr. Wolford’s employment agreement contains non-competition covenants restricting his ability to compete with us and non-solicitation covenants, applicable in each case during the term of the employment agreement and for a period of one year thereafter, customary covenants regarding our indemnification of Mr. Wolford, and covenants concerning confidentiality, rights to inventions and non-disparagement.

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COMPENSATION COMMITTEE REPORT

The Compensation Committee has reviewed and discussed the Compensation Discussion and Analysis included in this proxy statement with management of the company. Based on such review and discussions, the Compensation Committee has recommended to the Board of Directors that the Compensation Discussion and Analysis be included in this proxy statement.

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EXECUTIVE COMPENSATION

2022 Summary Compensation Table

The following table summarizes the compensation of our NEOs for 2022 using the disclosure rules required by the SEC. Mr. Wolford was hired as our President and CEO on May 7, 2021. Mr. Savarino was promoted from Vice President and Chief Accounting & Tax Officer to our Senior Vice President and Chief Financial Officer on September 20, 2021.

Notes and Narrative Disclosure to 2022 Summary Compensation Table

The following is a discussion of material factors necessary for an understanding of the information disclosed in the 2022 Summary Compensation Table. For a discussion of Mr. Wolford’s employment agreement, see “Compensation Discussion and Analysis—Employment Agreements” above.

Salary Column. The Salary amounts for 2021 and 2022 for all NEOs reflect a voluntary temporary 5% reduction in annual base salary in effect from August 16, 2021 through April 1, 2022.

Bonus Column. The amounts shown in the “Bonus” column for 2020 for Messrs. Savarino and Roland consist of cash payments received in April 2020 pursuant to the accelerated vesting of outstanding time-vesting long-term cash incentive awards granted in 2018 and 2019 based on service achieved through April 1, 2020. As a condition to the receipt and retention of the accelerated payments, each of the NEOs agreed to a clawback obligation providing that if he resigns from employment with our company or if the grantee’s employment is terminated by us for “cause” (as defined in our former Incentive Compensation Plan), in either case prior to the first anniversary of the payment date, the grantee would be required to repay the entire amount of the payment, net of applicable tax withholdings.

Stock Awards Column. All amounts in the “Stock Awards” column for 2022 and 2021 reflect the grant-date fair value of RSUs or restricted stock awarded in such years under our Stock Plan, computed in accordance with FASB ASC Topic 718. No RSUs or other stock awards were granted in 2020. For a description of the terms of the RSUs and restricted stock granted, see “Compensation Discussion and Analysis—2022 Long-Term Incentive Awards” and “—2021 Long-Term Incentive Awards” above.

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The amounts shown under “Stock Awards” for 2022 represent the grant date fair value of RSUs granted to each of the NEOs on May 12, 2022, consisting of performance-vesting RSUs and time-vesting RSUs. The number of performance-vesting and time-vesting RSUs awarded to the NEOs in 2022 were as follows:

The performance-vesting RSUs awarded to the NEOs during 2022 cliff vest in three years upon the attainment of target stock appreciation performance goals specified in their respective award agreements. The time-vesting RSUs granted to the NEOs during 2022 vest in equal amounts annually over a three-year period. In all cases, the RSUs are subject to forfeiture if the applicable vesting conditions are not met.

For Mr. Wolford, the amount shown under “Stock Awards” for 2021 represents the grant date fair value of restricted stock granted to him on May 8, 2021, consisting of performance-vesting shares and time-vesting shares. For Messrs. Savarino and Roland, the amounts shown under “Stock Awards” for 2021 represent the grant date fair value of RSUs granted to each of them as of July 1, 2021 (and, for Mr. Savarino, RSUs granted to him on October 1, 2021), consisting of performance-vesting RSUs and time-vesting RSUs.

The number of shares of performance-vesting and time-vesting restricted stock (Mr. Wolford) and the number of RSUs (Messrs. Savarino and Roland) awarded to the NEOs in 2021 were as follows:

The performance-vesting restricted stock awarded to Mr. Wolford during 2021 vests upon the attainment of a target level of Total Equity Value of the company, and the performance-vesting RSUs awarded to the other NEOs during 2021 vest upon the attainment of the safety, financial, business development and strategic performance goals specified in their respective award agreements. The time-vesting restricted stock awarded to Mr. Wolford in 2021 vests in three equal installments over a two-year period, and the time-vesting RSUs awarded to the other NEOs in 2021 vest in three equal installments over a three-year period. In all cases, the restricted stock and RSUs are subject to forfeiture if the applicable vesting conditions are not met.

Under the terms of the award agreements for the performance-vesting restricted stock and RSUs awarded to each NEO in 2022 and 2021, the maximum number of performance-vesting shares of restricted stock or RSUs that could vest regardless of how far our company exceeded the applicable performance goals, and the grant-date value of the awards of performance-vesting restricted stock or RSUs to each NEO in 2022 and 2021 assuming the highest level of performance conditions were achieved and the maximum number of performance-vesting shares of restricted stock and RSUs would vest, would have been as set forth in the table below:

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For a discussion of the valuation assumptions for the restricted stock and RSU awards, see Note 7, Stock-Based Compensation, to our audited consolidated financial statements for the fiscal year ended December 31, 2022 included in our Annual Report on Form 10-K for the fiscal year ended December 31, 2022, which has been filed with the SEC.

Non-Equity Incentive Plan Compensation Column. All amounts in the “Non-Equity Incentive Plan Compensation” column for 2022 consist of payments of annual cash incentive awards earned and paid pursuant to our 2022 Incentive Plan. For a description of 2022 Incentive Plan amounts paid to our NEOs for 2022, see “Compensation Discussion and Analysis—2022 Short-Term Incentive Program” above.

All amounts in the “Non-Equity Incentive Plan Compensation” column for 2021 consist of (a) payments of annual cash incentive awards earned and paid pursuant to our 2021 short-term incentive program and (b) quarterly cash payments awarded and earned during 2021 under a key employee incentive plan (or KEIP) that was in effect during our Chapter 11 reorganization and provided quarterly performance-based incentive opportunities for the period from April 1, 2020 through March 31, 2021 to certain executive-level employees, including Messrs. Savarino and Roland.

All amounts in the “Non-Equity Incentive Plan Compensation” column for 2020 consist of (a) quarterly cash payments awarded and earned during 2020 under the KEIP and (b) cash payments received in April 2020 pursuant to the accelerated vesting of outstanding performance-vesting long-term cash incentive awards granted in 2018 and 2019 under our former Incentive Compensation Plan based on service and actual company performance achieved through April 1, 2020. The amounts received for the accelerated vesting of 2018 and 2019 performance-vesting long-term cash incentive awards were as follows:

As a condition to the receipt and retention of the accelerated payments, each of the above NEOs agreed to a clawback obligation providing that if he resigns from employment with our company or if the grantee’s employment is terminated by us for “cause” (as defined in our former Incentive Compensation Plan), in either case prior to the first anniversary of the payment date, the grantee would be required to repay the entire amount of the payment, net of applicable tax withholdings.

The amounts received for quarterly cash payments awarded and earned under the KEIP for 2020, including an award payment made in February 2021 for the fourth calendar quarter of 2020, were as follows:

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All Other Compensation Column. The amounts shown in the “All Other Compensation” column for 2022 consist of the following:

2022 All Other Compensation Table

We suspended our employee Retirement Plan contribution matching program from November 2020 through January 1, 2022 in order to reduce costs. When we resumed the company match, we matched 50% of the first 6% of each participant’s compensation contributed. Effective on January 1, 2023, we increased the company match to 100% of the first 4% of each participant’s compensation contributed.

Under our SERP, in past years we have contributed to participants any portion of the applicable percentage of the base salary contribution and the matching contribution that cannot be contributed under the Retirement Plan because of the limitations within the Code. As a result of our chapter 11 reorganization, in 2021 we discontinued making SERP contributions to participants through the end of 2022. Participants in the SERP are fully vested in all amounts paid into the plan. The following table summarizes 2022 nonqualified deferred compensation of our NEOs under our SERP.

2022 Nonqualified Deferred Compensation

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2022 Grants of Plan-Based Awards

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Stock Plan

Our Stock Plan authorizes the grant of stock options, stock appreciation rights, restricted stock, RSUs, performance awards, and other stock-based awards or any combination thereof to eligible participants. Stock options intended to qualify as “incentive stock options” may only be granted to employees of the company or our subsidiaries. Subject to adjustment, the aggregate number of shares of company common stock that was initially available for issuance pursuant to awards under our Stock Plan is 11,111,111, of which 1,987,234 shares had been issued as of December 31, 2022 and 3,392,361 shares underlying outstanding awards of unvested restricted stock and RSUs had been reserved for issuance as of December 31, 2022. The shares issued pursuant to awards under our Stock Plan will be made available from shares currently authorized but unissued or shares currently held (or subsequently acquired) by the company as treasury shares, including shares purchased in the open market or in private transactions. During 2022, a total of 1,254,799 RSUs were granted under our Stock Plan. During 2022, no shares of restricted stock were granted under our Stock Plan.

Equity Compensation Plan Information

The following table provides information regarding securities authorized for issuance under our equity compensation plans as of December 31, 2022, categorized by (i) equity compensation plans previously approved by our stockholders and (ii) equity compensation plans not previously approved by our stockholders.

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Outstanding Equity Awards at Fiscal Year-End 2022

2022 Option Exercises and Stock Vested

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