Upland Software Inc

Item 1A. Risk Factors

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 failure to meet the continued listing requirements of Nasdaq could result in a delisting of our common stock, which could negatively impact the market price and liquidity of our common stock and our ability to access the capital markets.

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)). We have As provided in the notification letter from Nasdaq, we had 180 calendar days, or until October 5, 2026, to  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 Nasdaqs discretion. If we do not To regain compliance with Rule 5450(a)(1) by October 5, we effected the Reverse Stock Split. On July 8, 2026, we may be afforded a second 180 calendar day period to received notification from Nasdaq that we had regained compliance, subject to meeting applicable listing st with the minimum closing bid price requirement andard, as and written notice result, the matter of our intention to cure the deficiency durinoncompliance had been closed.

On July 31, 2026, we received a notification letter from Nasdaq notifying the second compliance period, includius that we no longer meet Nasdaqs $15 million minimum market value of publicly held shares requirement under Nasdaq Listing by effecting a Rule 5450(b)(23)(C) (the MVPHS Requirement) based on Nasdaqs reverse stock split if necessary.

If tiew of the market value of the Companys publicly held shares for the previous 30 consecutive business days. The closing bid price of onotification has no immediate effect on our common stock continues tolisting or trade below $1.00 per share, we inting on the NASDAQ Global Market.

Nasdaq has provided us a period of 180 calend ar days to iregain complement a reverse stock siance with the MVPHS Requirement, or until January 27, 2027 (the Complit to attempt to regain compliance, as disance Date). If, at any time before the Compliance Date, our market value of publicly held shares closed is at $15 million our defr more for a minitive proxy statement filed with the SEC on April 20,mum of ten consecutive business days, but generally no more than 2026. However, a reverse stock s consecutive business days, Nasdaq will provide written notification to us that we have regained complit reance with the MVPHS Requires stockholder approment.

We intend to actively monitor the market value of our publicly held shares. We may eval,uate and there can be no assurance that our stockholders wiconsider available options for regaining compliance with the MVPHS Requirement, as well approve ts applying for a transfer to The proposal or that a reNasdaq Capital Market. Howeverse stock split, if effected, would result i, there can be no assurance that we will take any specific action our r be able to regaining  compliance with the MVPHS Requirement or otherwise maintaining compliance with Nasdaqs continued  listing requirementules.

If we are unable to regain compliance withinby the applicable cure periodCompliance 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 Rule 5450(a)(1) 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.