Operating cash flow remains robust, evidenced by a 2024Q3 cash-to-net-income conversion ratio of 4.58, which facilitates active reinvestment into a $270.2 million portfolio purchase program in 2026Q1.
| Cash from Operations | 427.85M | 408.08M | 305.12M | 338.19M | 208.94M | 175.28M | 44.71M | 0 |
| Operating CF Growth % | 479.65% | 33.75% | -9.78% | 61.86% | 19.2% | 292.06% | - | - |
| Operating CF / Revenue % | 27.68% | 28.87% | 26.59% | 37.77% | 32.83% | 32.71% | 9.98% | 0% |
| Net Income | 184.76M | 170.03M | 118.83M | 85.98M | 39.4M | 38.32M | -74.64M | 10.88M |
| Depreciation & Amortization | 3.54M | 3.54M | 3.36M | 3.89M | 4.1M | 5.6M | 5.99M | 0 |
| Stock-Based Compensation | 11.96M | 11.96M | 9.39M | 8.53M | 2.29M | 522K | -25K | 0 |
| Deferred Taxes | 0 | 0 | -8.71M | 9.38M | 10.27M | 9.98M | -19.55M | 0 |
| Other Non-Cash Items | 234.66M | -51.48M | -12.59M | -4.34M | -327K | -30.7M | 53.26M | -10.88M |
| Working Capital Changes | 0 | 274.04M | 194.84M | 234.75M | 153.22M | 151.56M | 79.68M | 0 |
| Cash from Investing | -627.96M | -366.9M | -243.69M | -493.81M | -193.38M | -183.01M | -74.93M | 0 |
| Capital Expenditures | -3.6M | -5.45M | -4.22M | -3.11M | -2.33M | -2.15M | -2.07M | 0 |
| Acquisitions | -305.58M | 0 | -32.17M | 0 | 0 | -2.37M | 0 | 0 |
| Purchase of Investments | -1.02B | -916.85M | -636.56M | -636.42M | -327.2M | -363.54M | -201.69M | 0 |
| Sale/Maturity of Investments | 503.04M | 336.83M | 383.71M | 127.23M | 138.76M | 205.5M | 160.27M | 0 |
| Other Investing | 198.48M | 218.57M | 45.55M | 18.5M | -2.62M | -20.45M | -31.44M | 0 |
| Cash from Financing | 363.04M | 411K | -4.23M | 130.95M | 2.18M | 1.38M | 56.3M | 0 |
| Dividends Paid | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Share Repurchases | 0 | 0 | 0 | 0 | 0 | 0 | -540K | 0 |
| Stock Issued | 200K | 0 | 5.56M | 130.95M | 2.18M | 1.38M | 255K | 0 |
| Debt Issuance (Net) | 1.41M | 411K | -1000K | 1000K | 1000K | 1000K | -1000K | 0 |
| Other Financing | -8.66M | 0 | 0 | -1.35M | -2.18M | -1.38M | 0 | 0 |
| Net Change in Cash | 162.93M | 41.59M | 57.19M | -24.68M | 17.74M | -6.35M | 26.08M | 0 |
| Exchange Rate Effect | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Cash at Beginning | 199.11M | 157.53M | 100.34M | 125.01M | 107.27M | 113.62M | 87.55M | 0 |
| Cash at End | 316.43M | 199.11M | 157.53M | 100.34M | 125.01M | 107.27M | 113.62M | 0 |
| Free Cash Flow | 508.07M | 402.62M | 300.89M | 335.03M | 206.61M | 173.13M | 42.64M | 0 |
| FCF Growth % | 37.28% | 33.81% | -10.19% | 62.15% | 19.34% | 306.06% | - | - |
| FCF Margin % | 32.87% | 28.48% | 26.22% | 37.42% | 32.47% | 32.31% | 9.52% | 0% |
| FCF per Share | 12.13 | 9.62 | 7.27 | 8.74 | 5.5 | 5.33 | 1.22 | - |
Social inflation litigation exposure
According to the quarterly cash flow data, Skyward Specialty consistently generated positive operating cash flow, peaking at $171.4 million in 2025Q3, which suggests that the company is successfully maintaining a structural float advantage despite the inherent volatility of its specialized, non-commoditized insurance underwriting business model.
The consistent ability to generate operating cash flow significantly in excess of net income, as evidenced by the OCF/NI ratios frequently exceeding 2.0, indicates that the company is effectively managing its premium collection cycle relative to claim payments. This suggests that the underwriting engine is not only profitable but also serves as a reliable source of liquidity for investment activities.
Based on reported financial statements, the company actively recycled cash into its investment portfolio, with purchase activity reaching $270.2 million in 2026Q1, reflecting a strategic effort to deploy accumulated float into yield-generating assets to capitalize on the current interest rate environment for specialty insurers.
The frequent rotation between asset purchases and sales suggests a dynamic management approach to the investment portfolio, likely aimed at optimizing duration and yield. Investors should monitor whether this high level of portfolio turnover indicates a tactical response to market conditions or a potential need to maintain liquidity for upcoming claim settlements.
As indicated by the historical cash flow data, the company's operating cash flow frequently decouples from net income, with a notable OCF/NI ratio of 4.58 in 2024Q3, implying that non-cash accruals and reserve adjustments play a significant role in the reported earnings profile of the firm.
The wide variance between net income and operating cash flow warrants further investigation into the underlying reserve development patterns. This discrepancy may suggest that the company's earnings are heavily influenced by accounting estimates, which could mask the true cash-generative capacity of the underwriting segments during periods of rapid growth.
Based on the provided quarterly figures, claims and loss payments have trended upward, reaching $265.2 million in 2026Q1, which appears to correlate with the company's expansion and may indicate an increasing exposure to long-tail liability settlements that require careful monitoring of future cash outflows.
The steady rise in claims payments suggests that the company is reaching a scale where the timing of loss settlements could become a more significant factor in liquidity management. If the pace of claims payments continues to accelerate, it may pressure the current float-based investment strategy and necessitate a more conservative approach to capital allocation.
Quick answers to the most common questions about buying SKWD stock.
Skyward Specialty Insurance Group, Inc. (SKWD) generated $408.1M in net cash from operating activities in 2025. This reflects the cash generated directly from core business operations.
Skyward Specialty Insurance Group, Inc. (SKWD) generated $402.6M 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.
Skyward Specialty Insurance Group, Inc. (SKWD) spent $5.5M on capital expenditures in 2025. CapEx represents the cash invested in physical assets like property, plant, and equipment to maintain or grow the business.