Estimated tax guides

Read them in this order. Each one cites the IRS or SSA page it relies on, and each one marks what was not confirmed.

• Quarterly Estimated Taxes for Freelancers: 2027 Guide
  Five questions that sort the federal rules: who pays, when the dates fall, how the safe harbor works, how to pay, and what a short payment means.2 min read
• Estimated Tax Due Dates 2026–2027: Quarterly Calendar
  The four IRS periods, the 2026 weekdays, and the 2027 dates marked expected — including the uncertain January 2028 shift.2 min read
• Do I Need to Pay Quarterly Estimated Taxes? The $1,000 Rule
  Both parts of the IRS test have to apply: at least $1,000 after withholding and credits, and withholding under the smaller safe-harbor target.2 min read
• Self-Employment Tax: 15.3%, 92.35%, and the Wage Base
  12.4% Social Security plus 2.9% Medicare, generally on 92.35% of net profit, with the SSA wage base for 2026 and 2027.3 min read
• Estimated Tax Safe Harbor: 90%, 100%, and 110%
  The penalty test uses the smaller of 90% of this year and 100% of last year — 110% when prior AGI is over the threshold.2 min read
• How to Pay Estimated Taxes: IRS Direct Pay and Other Options
  Direct Pay is the IRS free bank-account option for estimated tax, with the limits and timing the IRS page describes.2 min read
• Underpayment Penalty and Form 2210: If You Miss a Date
  The penalty follows the amount, the period it was late, and the IRS quarterly interest rate. This page does not guess that rate.2 min read
• Expense and Invoice Tools for Freelancers, Compared
  A checklist for records that make quarterly estimates easier. No ranking, and no product link until one is actually filled in.1 min read
• Annualized Income Method: Uneven Freelance Income
  If your income is lumpy, the IRS annualized income installment method may lower early estimated payments. How Worksheet 2-9 and Form 2210 work.2 min read
• Skip the January Estimated Payment: File by Jan. 31
  Pub. 505: file your 2026 Form 1040 by January 31, 2027 and pay the balance, and you needn't make the January 15, 2027 payment. Farmers: March 1.2 min read
• Starting Estimated Payments Mid-Year: Which Date Applies
  If your first taxable income arrives after April 1, Pub. 505's Table 2-1 shows the first payment date and later installments. Examples and options.2 min read
• Raise W-4 Withholding Instead of Quarterly Payments?
  If you have a job and side income, Pub. 505 says you can add withholding on Form W-4 (Step 4(c)) to cover tax. Limits and timing the IRS lists.2 min read
• Income Jumped Mid-Year? Refigure Estimated Tax (Pub. 505)
  Pub. 505 Worksheet 2-12: how to recompute your remaining estimated payments after a big gain or raise, with the IRS's $1,800 to $4,100 example.3 min read
• Apply Your Tax Overpayment to Next Year's Estimated Tax
  Pub. 505: credit part or all of a 2025 overpayment to 2026 estimated tax. It counts as paid April 15 if you file on time, with no refund.3 min read
• Farmers and Fishermen: One Estimated Tax Payment Date
  Pub. 505: if two-thirds of gross income is from farming or fishing, one payment is due January 15, 2027, or none if you file by March 1 and pay in full.2 min read
• 1040-ES Worksheet: Calculate Estimated Tax Step by Step
  Walk through Pub. 505 Worksheet 2-1: expected income, deductions, tax, self-employment tax, 90% test and the $1,000 stop rule, with a made-up example.3 min read

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