X0508 4 2025-11-17 0 0001364954 CHEGG, INC CHGG 0001902785 Longo David C/O CHEGG, INC 3990 FREEDOM CIR SANTA CLARA CA 95054 0 1 0 0 CFO & Treasurer 0 Common Stock 2025-11-17 4 A 0 500000 0 A 1671200 D Common Stock 2025-11-17 4 A 0 500000 0 A 2171200 D Represents an annual grant of restricted stock units ("RSUs"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The shares underlying the RSUs will vest on 1/3 after one year and quarterly thereafter, subject to the Reporting Person's continued service on our board through the vesting date. Vesting Commencement Date is 11.11.2025 Represents the number of shares of Common Stock subject to performance-based restricted stock units ("PSUs") granted to the Reporting Person in 2025 (the "2025 PSUs") that shall now be subject to vesting following the Compensation Committee's determination of the achievement of certain performance measurements on 10/28/2028. The shares subject to the 2025 PSUs allocated to each performance metric shall vest as follows: 25% shall vest upon the stock appreciation by 50%, and then similarly in same tranches upon stock appreciation by 75%, 100% and 125% respectively with 25% each tranche subject to the Reporting Person's continued service through each vesting date. VCD is 10/28/2025 /s/ Damon Nakamura, Attorney-in-Fact for David Longo 2025-11-19