Chegg, Inc. (NYSE:CHGG), the leading student-first connected learning platform, today announced that it has entered into individual, privately negotiated repurchase agreements with certain holders of its outstanding 0% Convertible Senior Notes due 2026 (the "Notes") to repurchase approximately $8.9 million in aggregate principal amount of the Notes for an aggregate cash repurchase price of approximately $8.3 million (the "notes repurchase transactions"). The notes repurchase transactions were entered into in connection with Chegg's previously announced securities repurchase program and are expected to close on December 30, 2025, subject to the satisfaction of customary closing conditions. Following the closing, approximately $53.9 million aggregate principal amount of the Notes will remain outstanding and approximately $141.8 million will remain available under Chegg's securities repurchase program.

This press release does not constitute an offer to sell or a solicitation of an offer to buy these securities, nor shall there be any offer or sale of these securities in any state or jurisdiction in which the offer, solicitation, or sale would be unlawful prior to the registration or qualification thereof under the securities laws of any such state or jurisdiction.

About Chegg

Chegg is a learning platform helping businesses bring new skills to their workforce and giving lifelong learners and students the skills and confidence to succeed. Focused on the skilling market, which is $40 billion and growing, Chegg offers innovative tools for workplace readiness, professional upskilling, and language learning. Chegg also continues to offer students artificial intelligence (AI)-driven, personalized support. Chegg remains committed to its mission of improving learning outcomes and career opportunities for millions around the world. Chegg is a publicly held company based in Santa Clara, California and trades on the NYSE under the symbol CHGG. For more information, visit www.chegg.com.

Forward-Looking Statements

This press release contains "forward-looking" statements that are based on our beliefs and assumptions and on information currently available to us on the date of this press release. Forward-looking statements may involve known and unknown risks, uncertainties, and other factors that may cause our actual results, performance, or achievements to be materially different from those expressed or implied by the forward-looking statements. These statements include, but are not limited to, regarding the amount of the Notes to be repurchased, the amount of the Notes to remain outstanding following completion of the notes repurchase transactions, the amount to remain under our securities repurchase program following completion of the notes repurchase transactions, the ability to complete the notes repurchase transactions on the timeline described herein or at all and the final aggregate cash repurchase price for the notes repurchase transactions. Among the factors that could cause actual results to differ materially from those indicated in the forward-looking statements are: changes in the price of the common stock and changes in the convertible note and other capital markets. All information provided in this release is as of the date hereof, and Chegg undertakes no duty to update this information except as required by law. These and other important risk factors are described more fully in documents filed with the Securities and Exchange Commission, including Chegg's Annual Report on Form 10-K for the year ended December 31, 2024 filed with the Securities and Exchange Commission on February 24, 2025 and Chegg's Quarterly Report on Form 10-Q for the quarterly period ended September 30, 2025 filed with the Securities and Exchange Commission on November 11,2025, and could cause actual results to differ materially from expectations.

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Media Contact: press@chegg.com

Investor Contact: Tracey Ford, IR@chegg.com

Chegg Announces Repurchase of 0% Convertible Senior Notes Due 2026