UPLD · Upland Software, Inc. · Insider Trading

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Performance Stock Units ("PSUs") may vest at target amount of 6,666 and up to a maximum number of shares of 25,000 upon the achievement of the stock price hurdles for thirty (30) consecutive trading days immediately preceding such date during the three-year performance period beginning on August 17, 2026 and ending on August 16, 2029, the Performance Period. PSUs may vest as follows a) 6,666 shares at $20.00, b) 1,222 shares at $22.00, c) 1,223 shares at $24.00, d) 1,222 shares at $26.00, e) 1,222 shares at $28.00, f) 1,222 shares at $30.00, g) 1,223 shares at $32.00, h) 1,222 shares at $34.00, i) 1,222 shares at $36.00, j) 1,222 shares at $38.00, k) 1,223 shares at $40.00, l) 1,222 shares at $42.00, m) 1,222 shares at $44.00, n) 1,222 shares at $46.00, o) 1,223 shares at $48.00, and p) 1,222 shares at $50.00.

The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of September 30, 2026, provided that the participant continues to be a service provider through each such vesting date. Notwithstanding the foregoing, in the event of the participant's termination by the Company for any reason other than cause or if participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the restricted stock units shall become fully vested.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026.

This transaction was executed in multiple trades at prices ranging from $4.28 to $4.495. The price reported above reflects the weighted average sale price. The Reporting Person undertakes to provide upon request by the staff of the Securities and Exchange Commission, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate sale price.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026. These shares were sold to cover the tax withholding obligations in connection with the vesting of restricted stock units

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 03/09/2026. These shares were sold to cover the tax withholding obligations in connection with the vesting of restricted stock units

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

The restricted stock units vest in twelve equal quarterly installments starting on the Vesting Commencement Date of June 16, 2026, provided that the participant continues to be a service provider through each such vesting date. Notwithstanding the foregoing, in the event of the participant's termination by the Company for any reason other than cause or if participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the restricted stock units shall become fully vested.

Performance Stock Units ("PSUs") may vest at target amount of 133,333 and up to a maximum number of shares of 500,000 upon the achievement of the stock price hurdles for thirty (30) consecutive trading days immediately preceding such date during the three-year performance period beginning on May 1, 2026 and ending on May 1, 2029, the Performance Period. PSUs may vest as follows a) 133,333 shares at $2.00, b) 24,445 shares at $2.20, c) 24,444 shares at $2.40, d) 24,445 shares at $2.60, e) 24,444 shares at $2.80, f) 24,445 shares at $3.00, g) 24,444 shares at $3.20, h) 24,445 shares at $3.40, i) 24,444 shares at $3.60, j) 24,445 shares at $3.80, k) 24,444 shares at $4.00, l) 24,445 shares at $4.20, m) 24,444 shares at $4.40, n) 24,445 shares at $4.60, o) 24,444 shares at $4.80, and p) 24,444 shares at $5.00.

The performance stock units canceled effective April 30, 2026 in accordance with that certain Transition Agreement dated February 25, 2026 by and between the Issuer and Mr. McDonald.

The restricted stock units will vest on the earliest of (i) February 28, 2028, subject to Mr. McDonald's continued service on the Issuer's board of directors through such date, (ii) the termination of his service on the Board without Cause, as that term is defined in Mr. McDonald's employment agreement and (iii) a Change in Control, as defined in the Issuer's 2024 Omnibus Incentive Plan.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2025. The restricted stock units are subject to accelerated vesting under certain circumstances following a change of control.

The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2025, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant.

The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2025, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26, provided Mr. Chung continues to serve as a Director of Upland Software, Inc. (the "Issuer") as of each date. Upon any subsequent disposition of common stock of the Issuer covered by the RSUs, Mr. Chung will transfer the proceeds from any such disposition to HGGC, LLC or its affiliates ("HGGC") as required by an agreement between Mr. Chung and HGGC. As such, Mr. Chung disclaims all pecuniary interest in the reported securities.

Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Represents restricted stock units vesting as follows: one-half (1/2) shall vest on 12/16/25 and the remaining shall in two equal quarterly installments on each of 3/16/26 and 6/16/26.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Sales made to recognize general portfolio tax savings.

This transaction was executed in multiple trades at prices ranging from $2.31 to $2.43. The price reported above reflects the weighted average sale price. The Reporting Person undertakes to provide upon request by the staff of the Securities and Exchange Commission, the Issuer, or a security holder of the Issuer, full information regarding the number of shares sold at each separate sale price.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of June 16, 2025, provided that the participant continues to be a service provider through each such vesting date. Notwithstanding the foregoing, in the event of the participant's termination by the Company for any reason other than cause or if participant leaves for Good Reason after a Change in Control (as defined in the Plan), then 100% of the restricted stock units shall become fully vested.

The transaction indicated was conducted under an approved 10b5-1 Plan, adoption date of referenced 10b5-1 Plan is: 11/22/2024. These shares were sold to cover the tax withholding obligations in connection with the vesting of restricted stock units.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

Does not include 125,000 shares of common stock held in a trust for the benefit of Mr. McDonald's children of which The Bryn Mawr Trust Company of Delaware is the trustee.

Shares withheld by the issuer to satisfy tax withholding obligations in connection with the vesting of restricted stock units. This is not an open market sale of securities.

The restricted stock units vest in twelve equal quarterly installments starting on the three (3) month anniversary of the Vesting Commencement Date of December 16, 2024, provided that the participant continues to be a service provider through each such vesting date, except as otherwise specified in the Executive Employment Agreement between the Company and participant.