X0609 4 2026-04-30 0 0001505155 Upland Software, Inc. UPLD 0001094792 MCDONALD JOHN T false 900 S. CAPITAL OF TEXAS HWY LAS CIMAS IV, SUITE 300 AUSTIN TX 78746 1 0 0 0 0 Common Stock 2026-04-30 4 A 0 250000 0 A 2640887 D Common Stock 363738 I By National Financial Services as Cust FBO J. McDonald RRA Performance Share Unit 0 2026-04-30 4 D 0 250000 0 D Common Stock 250000 0 D 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. 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. 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. /s/ Michael D. Hill (as attorney-in-fact for J. McDonald) 2026-05-04