X0508 4 2025-10-27 0 0001505155 Upland Software, Inc. UPLD 0001576150 Chung David H S 900 S. CAPITAL OF TEXAS HWY LAS CIMAS IV, SUITE 300 AUSTIN TX 78746 1 0 0 0 0 Common Stock 2025-10-27 4 A 0 25000 0 A 124484 D 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. /s/ Michael D. Hill (as attorney-in-fact for D. Chung) 2025-10-29