Self-employed Floridians owe federal quarterly estimated taxes any time they'll owe $1,000 or more at tax time. Florida has no state income tax, so this is federal-only. The four deadlines for 2025 income: Q1 April 15 (covering Jan–Mar), Q2 June 16 (covering Apr–May, shifted from Jun 15 Sunday), Q3 September 15 (covering Jun–Aug), and Q4 January 15 2026 (covering Sep–Dec). The IRS calls them quarterly but they cover unequal periods. The safe-harbor rule eliminates the underpayment penalty entirely if you pay at least: (1) 90% of the current year's total tax, OR (2) 100% of the prior year's total tax if prior-year AGI was $150,000 or less, OR (3) 110% of the prior year's total tax if prior-year AGI was over $150,000. The 110% tier is the silent trap — most often missed by high-earning Florida sole proprietors. Underpayment penalty: interest-only at short-term federal rate plus 3%, currently around 7-8% annualized for 2024-2025, computed on Form 2210. Form 2210 has an annualized income method that can lower the penalty for irregular income patterns. The S-Corp owner nuance: W-2 salary from your S-Corp is processed through payroll and FICA-withheld, but S-Corp distributions have zero withholding while still being subject to federal income tax. Income tax on the distribution portion must come from quarterly estimated payments OR additional W-2 withholding via a fresh Form W-4. Florida-specific detail: Social Security wage base cap is $176,100 for 2025 (up from $168,600 in 2024), above which only the 2.9% Medicare portion of SE tax continues.