Penaltyproof

Freelancer? The IRS charged 15.7 million underpayment penalties last year.

Penaltyproof tells you how much to set aside from every payment, and the minimum to pay the IRS by each quarterly deadline so you never owe that penalty.

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$12.06B in estimated-tax penalties, ~$766 each.

IRS Data Book FY2025, Table 4-2

Example: Maya’s plan

Freelance product designer in California, single

Set aside from every payment

Paid to the IRS

Estimate for tax year 2026, not tax advice.

How it works

  1. Answer six questions

    Filing status, state, what clients have paid you so far, and last year’s tax if you know it. About two minutes.

  2. Get your two numbers

    The share of every payment to set aside, and the minimum to pay by the next deadline to stay clear of the penalty.

  3. Log each payment as it lands

    Tell us when a client pays and you see what to set aside from it. Log what you pay the IRS and the meter shows how much of the minimum is covered.

What you get

The minimum, not a guess
The IRS doesn’t charge the penalty if you pay its safe-harbor amount on time. We work out that amount from this year’s income or last year’s tax, whichever asks less of you.
Every deadline, with the amount
All four quarterly due dates with what to pay on each, plus your expected balance with the April return. Add them to your calendar in one tap.
Federal and your state
Self-employment tax, federal income tax and your state’s income tax, in one number to set aside.

Maya’s deadlines for 2026

  1. Q1  
  2. Q2  
  3. Q3  
  4. Q4  

$59 per tax year — less than one penalty.

Your plan and your first three logged payments are free. Pro adds unlimited logging, reading payouts from a screenshot, a plan for uneven income, and a CSV for your accountant. Or $9.99 a month.

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