Upland Software, Inc.

Item 1.01. Entry into a Material Definitive Agreement. On November 9, 2026, Upland Software, Inc. (the “Company”) entered into a Dividend Waiver Agreement (the “Waiver Agreement”) with Ulysses Aggregator, LP (the “Investor”), an affiliate of HGGC, LLC (“HGGC”) and the holder of all 115,000 outstanding shares of the Company's Series A Convertible Preferred Stock (the “Series A Preferred Stock”). Under the Waiver Agreement, effective October 1, 2026 the Investor waived, for an indefinite period, the accumulation and accrual of dividends on the Series A Preferred Stock, which accrue at 4.5% per annum and are paid in kind. Waived dividends are permanently forgiven and will not be reinstated or become payable, including upon any revocation of the waiver. The holders of a majority of the Series A Preferred Stock may revoke the waiver at any time, on a prospective basis, effective as of the first quarterly dividend period beginning at least 30 days after the Company receives written notice of the revocation. David Chung, Co-Chief Investment Officer and Managing Partner of HGGC, serves on the Company's Board of Directors as the Series A Director designated by the holders of the Series A Preferred Stock pursuant to the Certificate of Designation. The foregoing description of the Waiver Agreement does not purport to be complete and is qualified in its entirety by reference to the full text of the Waiver Agreement, which is filed as Exhibit 10.1 to this Current Report on Form 8-K and incorporated by reference herein.

Item 7.01. Regulation FD Disclosure. On November 9, 2026, the Company issued a press release announcing the Waiver Agreement. The press release is filed hereto as Exhibit 99.1 and is incorporated by reference herein. The information in this Item 7.01, including Exhibit 99.1, is being furnished and shall not be deemed “filed” for purposes of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or otherwise subject to the liabilities of that section, nor shall it be deemed incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as expressly set forth by specific reference in such a filing.