Operating cash flow remains volatile and negative at $41.2 million in 2025Q3, highlighting the difficulty in generating consistent liquidity while managing legacy insurance liabilities.
Octave Specialty Group, Inc. (OSG) cash flow statement — 30-year operating, investing & financing cash flows
| 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 | Dec'11 | Dec'10 | Dec'09 | Dec'08 | Dec'07 | Dec'06 | Dec'05 | Dec'04 | Dec'03 | Dec'02 | Dec'01 | Dec'00 | Dec'99 | Dec'98 | Dec'97 | Dec'96 |
|---|
| Cash from Operations | -62.13M | -52.28M | 762K | 200M | 70.37M | -131M | -175M | -311M | -1.54B | -212.77M | 843.54M | 87.54M | -971.51M | 186.22M | -613.9M | 3.56M | -2.09B | -1.85B | -1.42B | 945.38M | 903.13M | 1.01B | 949.7M | 1B | 805.49M | 671.83M | 481.33M | 454.4M | 337.66M | 324.52M | 190.63M |
| Operating CF Margin % | - | -20.81% | 0.32% | 160.35% | 131.25% | -53.04% | -112.18% | -62.7% | -303.79% | -34.54% | 168.06% | 13.58% | -240.83% | 27.16% | -71.11% | 1.22% | -480.73% | -47.45% | 51.68% | -22.43% | 49.29% | 62.42% | 67.76% | 78.89% | 84.03% | 70.96% | 53.99% | 85.21% | 73.89% | 85.02% | 42.09% |
| Operating CF Growth % | -794.87% | -6961.29% | -99.62% | 184.22% | 153.72% | 25.14% | 43.73% | 79.85% | -625.33% | -125.22% | - | 109.01% | -621.69% | 130.33% | -17358.87% | 100.17% | -12.77% | -30.06% | -250.53% | 4.68% | -10.36% | 6.09% | -5.37% | 24.6% | 19.89% | 39.58% | 5.93% | 34.57% | 4.05% | 70.23% | -17.58% |
| Net Income | -141.06M | -95.8M | -58.92M | 4M | -35.24M | -16M | -437M | -216M | 267.4M | -328.71M | 74.32M | 492.69M | 483.7M | 3.85B | -259.35M | -1.96B | 753.14M | -14.62M | -5.61B | -3.25B | 875.91M | 751.01M | 724.55M | 618.91M | 432.59M | 432.91M | 366.17M | 307.9M | 254M | 223.03M | 276.32M |
| Depreciation & Amortization | 47.51M | 41.95M | 19.95M | 5.23M | 3.79M | 57M | 58M | 295M | 108M | 152M | 175.83M | 172.77M | 155.41M | 102.61M | 3.07M | 3.73M | 3.65M | 2.98M | 3.16M | 3.94M | 6.15M | 1.55M | -1.58M | 21.53M | 12.34M | -12.44M | -9.36M | -1.5M | -2.4M | -1.33M | 383K |
| Stock-Based Compensation | -1.13M | 9.71M | 9.36M | 17M | 11.23M | 14M | 11M | 12M | 11.85M | 4.29M | 5.25M | 3.1M | 3.45M | 1.11M | 0 | -15.46M | 5.36M | 14.08M | 17.41M | 37.34M | 37.2M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Deferred Taxes | -5.03M | 0 | 0 | 0 | 0 | 2M | 8M | 36M | -28.93M | 5.67M | 9.24M | 260K | 4.84M | 600K | 2.65M | -142.94M | -225.53M | 1.24B | 822.29M | -2.2B | 5.05M | 71.28M | 19.99M | -12.28M | -52.11M | 4.99M | 24.3M | 3.27M | -2.03M | 12.02M | 4.5M |
| Other Non-Cash Items | -21.91M | -4.56M | 15.36M | 43.77M | 64.42M | -93M | 17M | -101M | -188.83M | -186.18M | -212.99M | 367.53M | 126.96M | -3.9B | 262.92M | 262.07M | -3.49B | -3.88B | 3.37B | 6.25B | -85.48M | 46.89M | -337.85M | -6.82M | 83.76M | 84.07M | -38.52M | -83.15M | 80.36M | 30.67M | 67.25M |
| Working Capital Changes | 2.29M | -3.58M | 15.02M | 130M | 26.17M | -95M | 168M | -337M | -1.71B | 140.17M | 791.89M | -948.82M | -1.75B | 126.66M | -390.61M | 1.86B | 863.93M | 787.65M | -31.3M | 101.62M | 64.3M | 139.5M | 549.07M | 363.91M | 320.03M | 178.22M | 151.71M | 224.32M | 1.77M | 84.59M | -20.04M |
| Change in Receivables | -51.31M | -49.58M | -11.33M | -21M | -13.48M | 48M | 44M | 77M | 91.3M | 76.9M | 172.33M | 169.03M | 452.41M | 167.6M | 407.86M | 394.12M | 1.3B | 944.27M | 0 | -9.54M | -21.87M | -16.27M | -2.83M | 370.27M | 335.11M | 195.16M | -2.02M | -2.7M | -47.2M | -9.41M | 0 |
| Change in Inventory | 0 | 0 | 0 | 0 | 0 | -6M | 121M | -409M | -1.78B | 291.17M | 0 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Change in Payables | 13.39M | 30.74M | 0 | 52M | 6M | 6M | -3M | -4M | -4.96M | -4.65M | -10.96M | -6.94M | -10.53M | 0 | -21.03M | 0 | 0 | -387.54M | 0 | 189.71M | 86.02M | 37.14M | 312.13M | 10.23M | -2.97M | 11.64M | 96.26M | 128.8M | 40.9M | 122.23M | -2.75M |
| Cash from Investing | 229.92M | 199.94M | -166.37M | 435M | -41.16M | 776M | 432M | 1B | 1.59B | 928.77M | -714.64M | -172.6M | 1.28B | -132.19M | 1.04B | 228.03M | 2.47B | 4.59B | 5.25B | -1.42B | -1.51B | -1.46B | -1.61B | -1.07B | -2.51B | -1.4B | 776.49M | -630.29M | -2.06B | -1.89B | -658.25M |
| Capital Expenditures | 0 | 0 | 0 | 0 | 0 | 0 | -178M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| CapEx % of Revenue | 0% | - | - | - | - | - | 114.1% | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Acquisitions | -218.53M | 189.36M | -229.66M | -7M | -18.44M | 0 | 104M | 543M | 348.87M | 0 | 0 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Investments | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Other Investing | 401.32M | -10.05M | -3.75M | 396M | 2.33M | 175M | 178M | 99M | -57.35M | 106.05M | 30.41M | -13M | -142.7M | -132.19M | 13.17M | -40.31M | 193.28M | 946.95M | 157.26M | 546.14M | -1.73B | -50.69M | -6.42M | 414.44M | -330.09M | 926.75M | -6.55M | 284M | -49.48M | 217.28M | 68.44M |
| Cash from Financing | -132.95M | -126.3M | 194.22M | -423M | -19.23M | -657M | -303M | -691M | -585.38M | -182.12M | -69.71M | 46.9M | -307.11M | -20.5M | -396.24M | -225.08M | -487.28M | -2.73B | -3.84B | 564.87M | 613.22M | 465.03M | 655.27M | 69.1M | 1.65B | 760.76M | -1.23B | 181.24M | 1.72B | 1.56B | 463.19M |
| Debt Issued (Net) | 5.06M | -32.53M | 147M | -97M | -1.54B | -467M | -121M | -166M | -224.34M | -98M | -49.03M | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
| Equity Issued (Net) | -14.5M | -12.94M | -11.7M | -5M | -22.22M | -6M | -3M | -3M | -11M | -1M | -2.71M | 0 | 0 | 16K | 0 | 0 | 0 | 0 | 1000K | -1000K | -1000K | -1000K | 1000K | 1000K | 1000K | -1000K | 1000K | -100K | -1000K | -1000K | -1000K |
| Dividends Paid | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | -817K | -12.51M | -15.8M | -79.57M | -69.91M | -58.8M | -50.91M | -44.74M | -40.25M | -35.94M | -32.21M | -29.37M | -26.57M | -24.16M | -21.5M |
| Share Repurchases | -31.5M | -29.94M | -11.7M | -5M | -14.22M | -6M | -3M | -3M | -1M | -1M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | -1.09M | -449.39M | -126.7M | -309.67M | -51.78M | -20.25M | -41.1M | -40.88M | -23.62M | -17.6M | -52.7M | -40.4M | -31.8M |
| Other Financing | -123.51M | -80.83M | 58.92M | -321M | 1.55B | -184M | -179M | -522M | -350.03M | -83.12M | -17.96M | -5.37M | -199.95M | -5.93M | -186.79M | -225.08M | -486.46M | -1.72B | 141.68M | 1.89M | -1.35B | -1.16B | 11.36M | 42.36M | -8.45M | -8.47M | -1.21B | 210.74M | 1.56B | 1.6B | 499.3M |
| Net Change in Cash | 32.71M | 22.82M | 28.05M | 213M | 9.97M | -12M | -46M | -2M | -541.19M | 532.68M | 55.28M | -38.16M | -3.47M | 186.32M | 27.84M | 6.5M | -102.58M | 5.42M | -16.12M | 92.06M | 4.25M | 8.34M | -4.58M | -1.37M | -50.76M | 31.15M | 31.84M | 5.35M | -1.02M | 1.52M | -4.43M |
| Free Cash Flow | -62.13M | -52.28M | 762K | 200M | 70.37M | -131M | -353M | -311M | -1.54B | -212.77M | 843.54M | 87.54M | -971.51M | 186.22M | -613.9M | 3.56M | -2.09B | -1.85B | -1.42B | 945.38M | 903.13M | 1.01B | 949.7M | 1B | 805.49M | 671.83M | 481.33M | 454.4M | 337.66M | 324.52M | 190.63M |
| FCF Margin % | -19.37% | -20.81% | 0.32% | 160.35% | 131.25% | -53.04% | -226.28% | -62.7% | -303.79% | -34.54% | 168.06% | 13.58% | -240.83% | 27.16% | -71.11% | 1.22% | -480.73% | -47.45% | 51.68% | -22.43% | 49.29% | 62.42% | 67.76% | 78.89% | 84.03% | 70.96% | 53.99% | 85.21% | 73.89% | 85.02% | 42.09% |
| FCF Growth % | -212.73% | -6961.29% | -99.62% | 184.22% | 153.72% | 62.89% | -13.5% | 79.85% | -625.33% | -125.22% | - | 109.01% | -621.69% | 130.33% | -17358.87% | 100.17% | -12.77% | -30.06% | -250.53% | 4.68% | -10.36% | 6.09% | -5.37% | 24.6% | 19.89% | 39.58% | 5.93% | 34.57% | 4.05% | 70.23% | -17.58% |
| FCF per Share | -1.37 | -1.11 | 0.02 | 4.38 | 1.52 | -2.82 | -7.65 | -6.77 | -33.15 | -4.69 | 18.45 | 1.90 | -20.70 | 3.97 | -6.52 | 0.04 | -22.16 | -19.65 | -15.11 | 9.18 | 8.40 | 9.21 | 8.56 | 9.18 | 7.39 | 6.16 | 4.48 | 4.24 | 3.15 | 3.09 | 1.80 |
| FCF Conversion (FCF/Net Income) | 0.44x | 0.22x | -0.00x | 55.07x | 0.13x | 7.71x | 0.40x | 1.44x | -5.78x | 0.65x | 11.27x | 0.18x | -2.01x | -0.74x | 2.39x | -0.00x | 2.77x | -126.65x | 0.25x | -0.29x | 1.03x | 1.34x | 1.31x | 1.62x | 1.86x | 1.55x | 1.31x | 1.48x | 1.33x | 1.46x | 0.69x |
| Interest Paid | 13.28M | 0 | 3.82M | 50M | 0 | 80M | 107M | 143M | 231.73M | 39M | 4.54M | 1.85M | 82.69M | 0 | 6.4M | 8.46M | 0 | 0 | 382.09M | 83.02M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Taxes Paid | -60K | 0 | 526K | 381K | 347K | 15M | 11M | 21M | 34.98M | 40M | 21.44M | 16.97M | 4.4M | 0 | 1.49M | 1.99M | 0 | 0 | 29.64M | 208.12M | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
Quick answers to the most common questions about buying OSG stock.
Octave Specialty Group, Inc. (OSG) generated $-52.3M in net cash from operating activities in 2025. This reflects the cash generated directly from core business operations.
Octave Specialty Group, Inc. (OSG) reported negative free cash flow of $52.3M in 2025, indicating capital requirements exceeded cash from operations.
Octave Specialty Group, Inc. (OSG) spent $0.0M 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, Octave Specialty Group, Inc. (OSG) spent $29.9M on share repurchases. This shows the company's commitment to returning capital to its equity investors.
Key Metrics
Top Statement Risk
Legacy liability settlement volatility
Metrics are mathematically derived from official filings.
Underwriting Cash Flow Remains Volatile
As reported in recent financial statements, Ambac's operating cash flow fluctuated significantly, reaching a negative $41.2 million in 2025Q3, which underscores the persistent difficulty in generating consistent net float from its evolving specialty P&C and legacy financial guarantee segments during this complex structural transition.
The erratic nature of operating cash flows suggests that the company is struggling to achieve a stable premium-to-claims equilibrium. Investors should monitor whether the growth in the Cirrata MGA platform can eventually offset the lumpy and unpredictable cash outflows associated with legacy loss settlements.
Investment Portfolio Liquidity Constraints Persist
Based on quarterly data, the company's investment activity shows a net purchase of $169.9 million in 2025Q3, indicating that management is actively deploying capital into the portfolio despite the ongoing cash burn observed in the core insurance operations during the same reporting period.
This deployment of capital appears to be a strategic attempt to bolster investment income, yet it warrants further investigation given the simultaneous pressure on operating cash. The reliance on portfolio purchases while operating cash flow is negative suggests a potential reliance on existing liquidity reserves to fund growth initiatives.
Legacy Claims Obscure Operational Performance
According to recent SEC filings, claims and loss payments reached $29.0 million in 2025Q3, reflecting the ongoing impact of legacy liabilities that continue to create significant cash outflows, which complicates the assessment of the underlying profitability of the newer specialty P&C underwriting business.
The persistence of these claims payments suggests that the legacy runoff remains a primary driver of cash volatility. It appears that until these legacy exposures are fully resolved, the company's cash flow profile will likely remain decoupled from the operational success of its newer, fee-based business lines.
Statutory Earnings Diverge From Cash
As indicated by the OCF/NI ratio of 0.37 in 2025Q3, there is a notable disconnect between reported net income and actual cash generation, which suggests that non-cash accounting adjustments continue to play a dominant role in the company's financial reporting and overall valuation.
This divergence highlights the difficulty in using GAAP net income as a proxy for the company's true economic health. The reliance on non-cash items may indicate that the company's reported losses are not fully reflective of the cash-based reality of its ongoing business transformation.