Free cash flow generation appears artificially supported by minimal capital expenditure, with the CapEx/Revenue ratio consistently remaining below 1.2% over the last ten quarters.
| Metric | TTM | Dec'25 | Dec'24 | Dec'23 | Dec'22 | Dec'21 | Dec'20 | Dec'19 | Dec'18 | Dec'17 | Dec'16 | Dec'15 | Dec'14 | Dec'13 | Dec'12 |
|---|
| Cash from Operations | 23.1M | 25.8M | 24.24M | 49.94M | 29.98M | 41.74M | 35.62M | 12.08M | 7.35M | 7.72M | 3.88M | -1.5M | 1.18M | -239K | 1.6M |
| Operating CF Margin % | - | 11.9% | 8.82% | 16.77% | 9.45% | 13.82% | 12.21% | 5.42% | 4.9% | 7.88% | 5.18% | -2.15% | 1.82% | -0.58% | 7.05% |
| Operating CF Growth % | -34.14% | 6.44% | -51.47% | 66.59% | -28.17% | 17.18% | 194.97% | 64.37% | -4.78% | 99.12% | 357.82% | -227.7% | 592.47% | -114.9% | - |
| Net Income | -14.29M | -38.9M | -112.73M | -179.87M | -68.41M | -58.21M | -51.22M | -45.37M | -9.95M | -18.73M | -13.51M | -13.66M | -20.12M | -9.2M | -2.51M |
| Depreciation & Amortization | 29.1M | 32.14M | 54.99M | 71.98M | 56.15M | 52.93M | 47.16M | 34.62M | 21.35M | 11.91M | 9.79M | 8.45M | 7.46M | 5.59M | 2.82M |
| Stock-Based Compensation | 7.39M | 9.11M | 15.27M | 22.87M | 41.6M | 53.87M | 41.69M | 25.75M | 14.13M | 9.98M | 4.33M | 2.74M | 12.3M | 498K | 92K |
| Deferred Taxes | -2.2M | -5.28M | -3.66M | -4.21M | -7.08M | -11.18M | -7.53M | -9.43M | 268K | -262K | 529K | 207K | -703K | -104K | -85K |
| Other Non-Cash Items | 10.17M | 33.52M | 86.42M | 138.46M | 26.95M | 6.71M | 7.82M | 9.24M | 3.55M | 191K | 1.28M | 1.36M | 589K | 1.58M | -771K |
| Working Capital Changes | -7.08M | -4.78M | -16.04M | 709K | -19.23M | -2.38M | -2.31M | -2.73M | -22M | 4.62M | 1.45M | -595K | 1.65M | 1.38M | 2.06M |
| Change in Receivables | -713K | 5.39M | -328K | 8.92M | 9.69M | -1.67M | 10.36M | 3.16M | -5.21M | -4.71M | -361K | 741K | -1.58M | 2.94M | -3.55M |
| Change in Inventory | 0 | 0 | 0 | 0 | 0 | -17.16M | -16.41M | -9.69M | -20.41M | 5.27M | 1.06M | -923K | -509K | 559K | -1.18M |
| Change in Payables | 1.64M | -5.72M | 1.34M | -6.9M | -7.17M | 10.87M | -3.08M | -73K | -3.4M | 1.25M | -1.45M | 157K | 1.12M | -1.11M | 875K |
| Cash from Investing | 5.11M | 8.8M | -882K | -1.22M | -63.22M | -93.53M | -68.97M | -217.76M | -161.69M | -110.78M | -13.23M | -9.41M | -7.08M | -28.57M | -33.31M |
| Capital Expenditures | -1.01M | -1.35M | -882K | -1.22M | -866K | -1.11M | -1.31M | -1.74M | -935K | -451K | -1.08M | -1.75M | -861K | -263K | -274K |
| CapEx % of Revenue | 0.5% | 0.62% | 0.32% | 0.41% | 0.27% | 0.37% | 0.45% | 0.78% | 0.62% | 0.46% | 1.44% | 2.5% | 1.33% | 0.64% | 1.2% |
| Acquisitions | 4.85M | 0 | 0 | 0 | -62.36M | -92.42M | -67.66M | -216.03M | -160.75M | -110.32M | -12.15M | -7.66M | -6.22M | -28.18M | -33.04M |
| Investments | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Other Investing | 1.09M | 10.15M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | -55K | -408K | -791K | 0 | -127K | -33.04M |
| Cash from Financing | -33.83M | -63.45M | -202.31M | -61.38M | 94.15M | -8.18M | 107.9M | 363.77M | 149.92M | 96.18M | 19.52M | -1.22M | 32.38M | 29.56M | 24.25M |
| Debt Issued (Net) | -32.77M | -62.17M | -188.4M | -40.4M | -5.4M | -5.41M | -5.79M | 241.57M | 166.57M | 61.13M | 22.12M | -844K | -5.77M | 10.17M | 12.87M |
| Equity Issued (Net) | -1.53M | -137K | -10.96M | -14.05M | 110.64M | -708K | 128.4M | 151.55M | 1.61M | 43.8M | -515K | -18K | 38.75M | 0 | 11.39M |
| Dividends Paid | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Share Repurchases | -397K | -137K | -10.96M | -14.06M | 0 | 0 | 0 | 0 | 0 | 0 | -515K | -18K | -97K | 0 | 0 |
| Other Financing | 470K | -1.13M | -2.95M | -6.93M | -11.09M | -2.06M | -14.71M | -29.35M | -18.26M | -8.75M | -2.08M | -359K | -599K | 19.39M | 0 |
| Net Change in Cash | -3.92M | -27.03M | -179.51M | -12.09M | 59.49M | -60.87M | 75M | 158.29M | -5.59M | -6.43M | 10.29M | -12.52M | 26.29M | 811K | -7.45M |
| Free Cash Flow | 22.09M | 24.45M | 23.36M | 48.72M | 29.11M | 40.62M | 34.3M | 10.34M | 6.41M | 7.26M | 2.8M | -3.25M | 316K | -502K | 1.33M |
| FCF Margin % | 10.94% | 11.27% | 8.5% | 16.36% | 9.18% | 13.45% | 11.76% | 4.64% | 4.28% | 7.42% | 3.74% | -4.65% | 0.49% | -1.22% | 5.84% |
| FCF Growth % | -16.01% | 4.67% | -52.06% | 67.36% | -28.33% | 18.42% | 231.77% | 61.26% | -11.74% | 159.74% | 186.06% | -1128.48% | 162.95% | -137.74% | - |
| FCF per Share | 7.58 | 8.54 | 8.41 | 15.19 | 9.23 | 13.41 | 12.88 | 4.48 | 3.21 | 3.95 | 1.70 | -2.18 | 0.65 | -0.50 | 13.34 |
| FCF Conversion (FCF/Net Income) | -1.55x | -0.66x | -0.22x | -0.28x | -0.44x | -0.72x | -0.70x | -0.27x | -0.74x | -0.41x | -0.29x | 0.11x | -0.06x | 0.03x | -0.64x |
| Interest Paid | 22.05M | 20.4M | 28.9M | 32.14M | 29.12M | 29.43M | 29.92M | 23.86M | 12.43M | 6.01M | 2.46M | 1.52M | 1.38M | 1.22M | 446K |
| Taxes Paid | 7.84M | 6.95M | 2.02M | 7.11M | 3.88M | 2.85M | 3.19M | 3.56M | 3.35M | 1.78M | 488K | 314K | 252K | 287K | 152K |
Terminal revenue base decay
According to the provided quarterly data, UPLD consistently reports net losses while maintaining positive operating cash flow, with the OCF/NI ratio frequently reaching extreme negative values, such as -4.56 in 2026Q1, highlighting a structural disconnect between GAAP profitability and the company's actual cash-generative capacity.
The persistent gap between net income and operating cash flow suggests that UPLD relies heavily on non-cash charges, such as significant depreciation and amortization, to mask underlying operational weakness. Investors should monitor whether this cash flow stability is sustainable or if it is merely a byproduct of aggressive cost-cutting and deferred investment in the legacy product portfolio.
As reported in financial statements, UPLD's free cash flow margins have fluctuated between 5.0% and 14.7% over the last ten quarters, a trend that appears to be driven more by the minimization of capital expenditures than by any meaningful growth in the company's core subscription revenue base.
While the company maintains positive free cash flow, the trajectory appears increasingly fragile as revenue continues to contract. The reliance on minimal capital intensity to preserve cash flow may indicate that the company is under-investing in the modernization of its legacy software assets, potentially accelerating the long-term erosion of its competitive moat.
Based on reported figures, UPLD's capital expenditure remains exceptionally low, with CapEx/Revenue ratios consistently below 1.2% over the last ten quarters, suggesting that the company is prioritizing short-term cash preservation over the necessary reinvestment required to maintain the technical relevance of its fragmented software portfolio.
The extremely low capital intensity warrants further investigation, as it may imply that the company is not adequately replacing or upgrading its aging software infrastructure. This strategy appears to be a defensive measure to protect cash flow in the face of declining revenue, but it likely increases the risk of technical obsolescence over the medium term.
As indicated by the provided financial data, UPLD consistently utilizes stock-based compensation, which averaged over $3 million per quarter in 2024, effectively acting as a non-cash expense that inflates reported operating cash flow while diluting existing shareholders and masking the true cost of maintaining the company's workforce.
The reliance on equity-based incentives suggests that the company may be struggling to manage its cash-based compensation expenses within the constraints of its shrinking revenue. Analysts should adjust cash flow metrics to account for this dilution, as the current reported figures likely overstate the company's ability to generate value for equity holders.
Quick answers to the most common questions about buying UPLD stock.
Upland Software, Inc. (UPLD) generated $25.8M in net cash from operating activities in 2025. This reflects the cash generated directly from core business operations.
Upland Software, Inc. (UPLD) generated $24.4M in free cash flow in 2025. Free cash flow is the cash left over after capital expenditures, which can be used to pay dividends, repurchase shares, or pay down debt.
Upland Software, Inc. (UPLD) spent $1.4M on capital expenditures in 2025. CapEx represents the cash invested in physical assets like property, plant, and equipment to maintain or grow the business.
In 2025, Upland Software, Inc. (UPLD) spent $0.1M on share repurchases. This shows the company's commitment to returning capital to its equity investors.