CHGG

SEC source: 0001364954-26-000095 · wk-form4_1791903475.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,715,660

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

F2 · balance_after: This includes the unvested PSUs granted to the reporting person

SEC source: 0001234658-26-000008 · wk-form4_1789473038.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,627,441

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-26-000090 · wk-form4_1786730865.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: Plan reported

Ownership: Direct

Disclosed balance after: 376,311

F1 · shares: The transaction was effected pursuant to a Rule 10b5-1 trading plan adopted by the reporting person on May 14, 2026

F2 · price: The price reported in Column 4 is a weighted average price. These shares were sold in multiple transactions at prices ranging from $0.7625 to $0.7978, inclusive. The reporting person undertakes to provide Chegg Inc., the Securities and Exchange Commission staff or the applicable exchange full information regarding the number of shares sold at each separate price upon request.

SEC source: 0001364954-26-000079 · wk-form4_1783968190.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,779,261

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

F2 · balance_after: This includes the unvested PSUs granted to the reporting person

SEC source: 0001364954-26-000077 · wk-form4_1782122865.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 430,658

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000071 · wk-form4_1782122761.xml · nonDerivative · entry 1

SCHLEIN TED · CIK 0001242733 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 174,784

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date

F2 · balance_after: Includes 55,000 RSUs granted on June 12, 2026, that are directly owned by the Reporting Person, but were reported as owned by the Schlein Family Trust Dated April 20, 1999

SEC source: 0001364954-26-000075 · wk-form4_1782122828.xml · nonDerivative · entry 1

Martin Marcela · CIK 0001856602 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 432,434

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000073 · wk-form4_1782122798.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 465,281

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000058 · wk-form4_1781574201.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 310,874

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000062 · wk-form4_1781574580.xml · nonDerivative · entry 1

SCHLEIN TED · CIK 0001242733 · Director

10b5-1 filing: No plan indicated

Ownership: Indirect · Schlein Family Trust Dtd 4/20/99

Disclosed balance after: 579,663

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

F2 · balance_after: 524,663 shares reported as indirectly owned by the Schlein Family Trust include (i) 444,193 shares previously reported as directly owned by the reporting person that were subsequently transferred to the trust and (ii) 80,470 shares held by the trust that were reported when acquired, which were inadvertently omitted in the subsequent Form4.

SEC source: 0001364954-26-000060 · wk-form4_1781574269.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,633,778

F3 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-26-000060 · wk-form4_1781574269.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,640,115

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-26-000056 · wk-form4_1781574140.xml · nonDerivative · entry 1

Martin Marcela · CIK 0001856602 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 312,650

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000054 · wk-form4_1781574078.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 345,497

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-26-000064 · wk-form4a_1781660305.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,633,778

F3 · kind: This Form 4/A amends the prior filing to correct the transaction code from "S" to "F". The transaction represents shares withheld by the Issuer to satisfy tax withholding obligations in connection with the vesting and settlement of RSUs in an exempt transaction pursuant to Section 16b-3(e).

SEC source: 0001364954-26-000064 · wk-form4a_1781660305.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,640,115

F2 · kind: This Form 4/A amends the prior filing to correct the transaction code from "S" to "F". The transaction represents shares withheld by the Issuer to satisfy tax withholding obligations in connection with the vesting and settlement of PSUs in an exempt transaction pursuant to Section 16b-3(e).

SEC source: 0001364954-26-000028 · wk-form4_1776214645.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,842,862

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

F2 · balance_after: This includes the unvested PSUs granted to the reporting person

SEC source: 0001364954-26-000022 · wk-form4_1773450859.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,618,071

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-26-000017 · wk-form4_1771414224.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · PRESIDENT, CEO, EXEC CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,625,075

F1 · kind: The reported transaction represents an open market purchase of common stock of CHGG by the Reporting Person following pre-clearance pursuant to the insider trading policy of the company.

F2 · price: The price reported in this Column is a weighted average price. These shares were purchased in multiple transactions at prices ranging from $0.5576 to $0.5641, inclusive. The Reporting Person has provided to the Issuer, and undertakes to provide any security holder of the Issuer or the staff of the Securities and Exchange Commission, upon request, full information regarding the number of shares purchased at each separate price within the range set forth in this Form 4.

SEC source: 0001364954-26-000002 · wk-form4_1768494974.xml · nonDerivative · entry 2

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,906,462

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-26-000002 · wk-form4_1768494974.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,169,385

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000145 · wk-form4_1765822781.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,525,075

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000133 · wk-form4_1763572844.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 255,874

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000127 · wk-form4_1763572543.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 7,531,412

F2 · kind: 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

SEC source: 0001364954-25-000127 · wk-form4_1763572543.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 3,681,412

F1 · kind: Represents an award of restricted stock units ("RSU", and each an "RSU"). Each RSU represents a contingent right to receive one share of common stock of the Issuer upon vesting. The RSU will vest 3yr 1/3rd Cliff after 1-year, quarterly vesting thereafter. Vesting Commencement Date is 10/28/2025

SEC source: 0001364954-25-000131 · wk-form4_1763572687.xml · nonDerivative · entry 1

SCHLEIN TED · CIK 0001242733 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 444,193

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000135 · wk-form4_1763572887.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 290,497

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000137 · wk-form4_1763572994.xml · nonDerivative · entry 1

Martin Marcela · CIK 0001856602 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 257,650

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000129 · wk-form4_1763572633.xml · nonDerivative · entry 2

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,171,200

F2 · shares: 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

SEC source: 0001364954-25-000129 · wk-form4_1763572633.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,671,200

F1 · shares: 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

SEC source: 0001364954-25-000109 · wk-form4_1760540916.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,171,200

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001234658-25-000003 · wk-form4_1757978840.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,031,412

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001586632-25-000004 · wk-form4_1757979007.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,464,391

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001586632-25-000004 · wk-form4_1757979007.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,482,884

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000088 · wk-form4_1752617506.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,172,356

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000075 · wk-form4_1750113536.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,037,749

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000075 · wk-form4_1750113536.xml · nonDerivative · entry 1

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,039,705

F1 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000074 · wk-form4_1750113390.xml · nonDerivative · entry 2

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,485,090

F2 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000074 · wk-form4_1750113390.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,540,480

F1 · shares: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the performance stock units ("PSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000065 · wk-form4_1749581608.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 85,742

SEC source: 0001364954-25-000083 · wk-form4_1750718961.xml · nonDerivative · entry 1

BUDIG RENEE VARNI · CIK 0001658725 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 140,742

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000085 · wk-form4_1750718980.xml · nonDerivative · entry 1

SCHLEIN TED · CIK 0001242733 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 329,061

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000082 · wk-form4_1750718951.xml · nonDerivative · entry 1

SARNOFF RICHARD · CIK 0001236133 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 369,089

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000084 · wk-form4_1750718970.xml · nonDerivative · entry 1

Levine Marne L. · CIK 0001586643 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 175,365

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000081 · wk-form4_1750718941.xml · nonDerivative · entry 1

Martin Marcela · CIK 0001856602 · Director

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 142,518

F1 · shares: Represents an annual grant of restricted stock units ("RSUs") for board service. 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 the one-year anniversary of the grant date, subject to the Reporting Person's continued service on our board through the vesting date.

SEC source: 0001364954-25-000057 · wk-form4_1748365275.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CHIEF OPERATING OFFICER

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,555,497

F1 · shares: On May 22, 2025, the reporting person transferred 144,448 shares of common stock to the Nathan Schultz and Debbie Schultz Co-TTEE Schultz Family Trust.

F2 · balance_after: Includes 8000 shares acquired under the 2013 Amended and Restated Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2025.

SEC source: 0001364954-25-000062 · wk-form4a_1749250283.xml · nonDerivative · entry 1

Schultz Nathan J. · CIK 0001586632 · CEO & PRESIDENT

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,555,497

F1 · shares: On May 22, 2025, the reporting person transferred 144,448 shares of common stock to the Nathan Schultz and Debbie Schultz Co-TTEE Schultz Family Trust.

F2 · balance_after: Includes 8000 shares acquired under the 2013 Amended and Restated Chegg, Inc. Employee Stock Purchase Plan (ESPP) on May 15, 2025.

SEC source: 0001364954-25-000036 · wk-form4_1744751474.xml · nonDerivative · entry 1

Longo David · CIK 0001902785 · CFO & Treasurer

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 1,173,997

F1 · shares: 1. Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000025 · wk-form4_1741989911.xml · nonDerivative · entry 3

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,090,401

F3 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreements governing the PSUs to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of the PSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.

SEC source: 0001364954-25-000025 · wk-form4_1741989911.xml · nonDerivative · entry 2

ROSENSWEIG DANIEL · CIK 0001234658 · Director · EXECUTIVE CHAIRMAN

10b5-1 filing: No plan indicated

Ownership: Direct

Disclosed balance after: 2,092,179

F2 · kind: Exempt transaction pursuant to Section 16b-3(e) payment of exercise price or tax liability by delivering or withholding securities incident to the receipt, exercise or vesting of a security issued in accordance with Rule 16b-3. All of the shares reported as disposed of in this Form 4 were automatically withheld by the Issuer in accordance with the agreement governing the restricted stock units ("RSUs") to satisfy federal and state tax withholding obligations of the Reporting Person resulting from the vesting and settlement of RSUs. The Reporting Person did not sell any of the shares reported on this Form 4 item; such shares were cancelled by the Issuer in accordance with the foregoing.