Operating cash flow reached $67.6M in Q2 2026, with an OCF/NI ratio of 1.38, indicating strong cash conversion, though claims payments rose 42% YoY to $276.7M.
Skyward Specialty Insurance Group, Inc. (SKWD) cash flow statement — 7-year operating, investing & financing cash flows
| Metric | TTM | Dec'25 | Dec'24 | Dec'23 | Dec'22 | Dec'21 | Dec'20 | Dec'13 |
|---|
| Cash from Operations | 407.3M | 408.08M | 305.12M | 338.19M | 208.94M | 175.28M | 44.71M | 0 |
| Operating CF Growth % | 135.54% | 33.75% | -9.78% | 61.86% | 19.2% | 292.06% | - | - |
| Operating CF / Revenue % | 24.83% | 28.87% | 26.59% | 37.77% | 32.83% | 32.71% | 9.98% | 0% |
| Net Income | 187.9M | 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 | 75.77M | -51.48M | -12.59M | -4.34M | -327K | -30.7M | 53.26M | -10.88M |
| Working Capital Changes | 128.14M | 274.04M | 194.84M | 234.75M | 153.22M | 151.56M | 79.68M | 0 |
| Cash from Investing | -580.22M | -366.9M | -243.69M | -493.81M | -193.38M | -183.01M | -74.93M | 0 |
| Capital Expenditures | -5.13M | -5.45M | -4.22M | -3.11M | -2.33M | -2.15M | -2.07M | 0 |
| Acquisitions | -308.93M | 0 | -32.17M | 0 | 0 | -2.37M | 0 | 0 |
| Purchase of Investments | -979.95M | -916.85M | -636.56M | -636.42M | -327.2M | -363.54M | -201.69M | 0 |
| Sale/Maturity of Investments | 373.58M | 336.83M | 383.71M | 127.23M | 138.76M | 205.5M | 160.27M | 0 |
| Other Investing | 341.86M | 218.57M | 45.55M | 18.5M | -2.62M | -20.45M | -31.44M | 0 |
| Cash from Financing | 302.27M | 411K | -4.23M | 130.95M | 2.18M | 1.38M | 56.3M | 0 |
| Dividends Paid | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
| Share Repurchases | -10.76M | 0 | 0 | 0 | 0 | 0 | -540K | 0 |
| Stock Issued | 200K | 0 | 5.56M | 130.95M | 2.18M | 1.38M | 255K | 0 |
| Debt Issuance (Net) | 411K | 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 | 129.36M | 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 | 316.43M | 157.53M | 100.34M | 125.01M | 107.27M | 113.62M | 87.55M | 0 |
| Cash at End | 302.52M | 199.11M | 157.53M | 100.34M | 125.01M | 107.27M | 113.62M | 0 |
| Free Cash Flow | 404.17M | 402.62M | 300.89M | 335.03M | 206.61M | 173.13M | 42.64M | 0 |
| FCF Growth % | 8.83% | 33.81% | -10.19% | 62.15% | 19.34% | 306.06% | - | - |
| FCF Margin % | 24.64% | 28.48% | 26.22% | 37.42% | 32.47% | 32.31% | 9.52% | 0% |
| FCF per Share | 9.65 | 9.62 | 7.27 | 8.74 | 5.5 | 5.33 | 1.22 | - |
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.
Key Metrics
Top Statement Risk
Reserve adequacy in growth
Metrics are mathematically derived from official filings.
Underwriting Cash Generation Strengthens
Skyward's operating cash flow reached $67.6M in Q2 2026, up from $21.0M in Q2 2024, reflecting robust premium collections and disciplined claims payments, as per the latest quarterly data.
The OCF/NI ratio of 1.38 in Q2 2026 indicates that cash generation is outpacing net income, a sign of high-quality earnings. This trend is consistent with the company's strong underwriting discipline, as evidenced by the combined ratio of 86.7% in the same period. The consistent positive OCF across quarters suggests that the company is effectively converting premium growth into cash, which supports its ability to fund operations and invest in growth.
Claims Payments Rise with Growth
Claims and loss payments escalated to $276.7M in Q2 2026 from $195.0M in Q2 2024, a 42% increase, according to reported cash flow data, indicating rising loss costs.
The increase in claims payments aligns with the company's rapid premium growth, but the pace of claims growth (42% over two years) is slightly below premium growth (48.7% YoY in Q2 2026), suggesting that loss ratios may be improving. However, the absolute rise in claims payments warrants monitoring for potential reserve adequacy issues, especially in long-tail liability lines. The company's ability to maintain underwriting profitability despite higher claims outflows will be key to sustaining cash generation.
Investment Portfolio Cash Flows Active
Skyward's investment purchases outpaced sales in Q2 2026, with net purchases of $171.5M, as reported in the cash flow statement, indicating active portfolio management.
The company has been consistently investing in its portfolio, with purchases exceeding sales in most quarters. This suggests that Skyward is deploying its float into fixed-income securities to capture higher yields in the current rate environment. The net investment activity is a source of cash outflow, but it is more than offset by strong operating cash flow, indicating that the company is effectively managing its liquidity while seeking to enhance investment income.
Cash Conversion Exceeds Earnings
Skyward's operating cash flow to net income ratio averaged 2.3 over the last ten quarters, as per financial statements, indicating that cash generation is significantly higher than reported earnings.
The consistently high OCF/NI ratio suggests that net income is being supported by non-cash items, such as reserve releases, which may not be sustainable. While this is a positive sign of cash generation, investors should be cautious about the quality of earnings, as favorable prior-year reserve development may be inflating net income. The company's ability to maintain this cash conversion will depend on its underwriting discipline and reserve adequacy.
Capital Return Minimal, Cash Retained
Skyward paid no dividends and repurchased only $10.8M in shares in Q2 2026, as per cash flow data, indicating a focus on retaining capital for growth.
The company's capital return to shareholders is minimal, with no dividends and sporadic buybacks. This suggests that management is prioritizing reinvestment in the business, likely to support its rapid expansion and maintain a conservative capital structure. The low debt-to-equity ratio of 0.12% further supports this strategy, but investors may eventually expect a more aggressive capital return policy as the company matures.
Growth May Mask Reserve Risks
Rapid premium growth of 48.7% YoY in Q2 2026, as reported in the income statement, may lead to inadequate IBNR reserves, potentially impacting future cash flows.
The company's aggressive expansion into new lines could result in under-reserving, especially if loss development emerges unfavorably. While current cash flows are robust, the sustainability of this performance is uncertain. Investors should monitor the adequacy of loss reserves, particularly in long-tail liability lines, as any shortfall could lead to higher claims payments and reduced cash generation in the future.