The aggregate number and percentage of the Common Stock beneficially owned by each Reporting Person are set forth on Rows 11 and 13 of the cover pages of this Schedule 13D and are incorporated herein by reference. Calculations of the percentage of the shares of Common Stock beneficially owned are based on the 2,838,697 shares of Common Stock outstanding as of November 2, 2026, as reported in the Issuer's Quarterly Report on Form 10-Q filed on November 4, 2026, as adjusted to include the 789,686 shares of Common Stock issuable upon conversion of the 115,000 shares of Series A Preferred Stock. As of September 15, 2026, Aggregator LP directly holds 115,000 shares of Series A Preferred Stock (after giving effect to the accrual of dividends in kind paid thereunder as of September 15, 2026), which is currently convertible into 789,686 shares of Common Stock, calculated as the sum of the principal investment amount and accrued dividends, divided by a conversion price equal to $175.00 per share (the "Conversion Price"), and Bloom Acquisitions 1, LP, a Delaware limited partnership and an affiliate of Aggregator LP, directly holds, in the aggregate, 25,172 shares of Common Stock. Neither the filing of this Schedule 13D nor any of its contents shall be deemed to constitute an admission that any of the foregoing or the Reporting Persons are the beneficial owners of the Common Stock referred to herein for purposes of Section 13(d) of the Securities Exchange Act of 1934, as amended, or for any other purpose.

The aggregate number of shares of Common Stock as to which each Reporting Person has sole power to vote or to direct the vote, shared power to vote or to direct the vote, sole power to dispose or to direct the disposition, or shared power to dispose or to direct the disposition is set forth on Rows 7 through 10 of the cover pages of this Schedule 13D and is incorporated herein by reference. Aggregator GP exercises sole voting and investment discretion over the reported securities. Holdings is the sole shareholder and director of Fund IV GP Ltd., the sole member of Aggregator GP, and therefore Holdings and the Holdings Members may be deemed to beneficially own the reported securities but disclaim such beneficial ownership.

Except as otherwise disclosed in this Amendment No. 5, the Reporting Persons have effected no transactions in Common Stock within the prior 60 days.

Except as otherwise described in this Amendment No. 5, no one other than the Reporting Persons has the right to receive, or the power to direct the receipt of, dividends from, or the proceeds from the sale of, any of the Common Stock beneficially owned by the Reporting Persons as described in this Item 5.

On November 9, 2026, the Issuer entered into a Dividend Waiver Agreement (the "Waiver Agreement") with Aggregator LP. Under the Waiver Agreement, effective October 1, 2026 Aggregator LP 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 Issuer receives written notice of the revocation. 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 herewith as Exhibit 99.5 to this Amendment No. 5 and is incorporated herein by reference.

99.5 Dividend Waiver Agreement, dated as of November 9, 2026, by and between Upland Software, Inc. and Ulysses Aggregator, LP (incorporated by reference from Exhibit 10.1 to the Issuer's Current Report on Form 8-K with the Securities and Exchange Commission on November 9, 2026).