Upland Software, Inc.

In addition to the other information set forth in this report, you should carefully consider the factors discussed in Part I, “Item 1A. Risk Factors” in our 2025 Annual Report on Form 10-K, which could materially affect our business, financial condition or future results. There have been no material changes during 2026 to the risk factors that were included in the Company's Annual Report on Form 10-K, other than as set forth below.

Our common stock is listed on the Nasdaq Global Market, or Nasdaq. In order to maintain this listing, we must satisfy the continued listing requirements and standards of Nasdaq, including a minimum closing bid price requirement for our common stock of $1.00 per share and that the market value of publicly held shares of our common stock is at least $15 million. On April 7, 2026, we received a notification letter from Nasdaq notifying us that, for the last 30 consecutive business days, the closing bid price for our common stock has been below the minimum $1.00 per share required for continued listing on Nasdaq pursuant to Nasdaq Listing Rule 5450(a)(1) (“Rule 5450(a)(1)”). As provided in the notification letter from Nasdaq, we had 180 calendar days to regain compliance with Rule 5450(a)(1) by maintaining a closing bid price of at least $1.00 per share for a minimum of 10 consecutive trading days, subject to Nasdaq’s discretion. To regain compliance with Rule 5450(a)(1), we effected the Reverse Stock Split. On July 8, 2026, we received notification from Nasdaq that we had regained compliance with the minimum closing bid price requirement and, as a result, the matter of our noncompliance had been closed.

On July 31, 2026, we received a notification letter from Nasdaq notifying us that we no longer meet Nasdaq’s $15 million minimum market value of publicly held shares requirement under Nasdaq Listing Rule 5450(b)(2&3)(C) (the “MVPHS Requirement”) based on Nasdaq’s review of the market value of the Company’s publicly held shares for the previous 30 consecutive business days. The notification has no immediate effect on our listing or trading on the Nasdaq Global Market.

Nasdaq has provided us a period of 180 calendar days to regain compliance with the MVPHS Requirement, or until January 27, 2027 (the “Compliance Date”). If, at any time before the Compliance Date, our market value of publicly held shares closes at $15 million or more for a minimum of ten consecutive business days, but generally no more than 20 consecutive business days, Nasdaq will provide written notification to us that we have regained compliance with the MVPHS Requirement.

We intend to actively monitor the market value of our publicly held shares. We may evaluate and consider available options for regaining compliance with the MVPHS Requirement, as well as applying for a transfer to The Nasdaq Capital Market. However, there can be no assurance that we will take any specific action or be able to regain compliance with the MVPHS Requirement or otherwise maintain compliance with Nasdaq listing rules.

If we are unable to regain compliance by the Compliance Date, including any available extension, our common stock would be subject to delisting from Nasdaq. Further, even if we regain compliance, we may not be able to sustain compliance with the MVPHS Requirement in the long term or with the additional continued listing requirements and standards of Nasdaq. A delisting could significantly reduce the liquidity and market price of our common stock, limit investors’ ability to buy and sell our common stock, reduce analyst coverage, and negatively affect our ability to access the capital markets or complete strategic transactions on favorable terms, or at all. Delisting could also trigger certain contractual provisions or investor concerns that may further adversely affect us.