🗓 Your Q2 payment is due in 11 days

Good morning! Your second quarterly estimated tax payment is due June 15, which is 11 days from now, which is probably nine days fewer than you thought you had.

This week’s lineup:

The Basics

🗓 Quarterly taxes: the calendar, the logic and the deadlines that actually matter

The U.S. tax system runs on a principle the IRS calls “pay as you earn,” which is a polite way of saying the government would like its money now, not in one dramatic lump sum every April. If you’re a W-2 employee, your employer handles this through withholding and you never think about it. If you’re self-employed, freelance, own a business or earn income nobody is withholding taxes on, quarterly estimated payments are how you stay current.

You generally need to pay if you expect to owe $1,000 or more after subtracting withholding and credits. The IRS does not send a bill, a reminder or a politely worded nudge. You’re expected to know.

Here are the 2026 deadlines:

You may notice these “quarters” are not actually quarters. Q2 covers two months. Q4 covers four. The IRS has never explained why with any conviction. The schedule is a historical artifact from when the fiscal year started March 1, and rather than fix it at any point in the past century, the agency simply kept going. The practical effect is that Q2 arrives nine weeks after Q1, which catches most first-time filers off guard.

Miss a deadline and the IRS charges interest on what you underpaid, running from the due date until you pay. It’s not dramatic. It’s just money you didn’t need to spend.

📋Get IRS Form 1040-ES (Estimated Tax for Individuals) →

The Strategy

💸 How to calculate your estimated taxes without losing your mind

Most business owners calculate their estimated taxes by staring at their bank balance, experiencing a brief wave of dread and then sending the IRS a number that feels approximately right. This is not a method. This is astrology with a checkbook.

The IRS offers two legitimate approaches.

The prior-year safe harbor is the simpler one. If you pay at least 100% of last year’s total tax liability in four equal installments, you won’t owe an underpayment penalty, even if your actual bill turns out higher. If your AGI exceeded $150,000 ($75,000 married filing separately), the threshold is 110%.

Find line 24 on last year’s 1040. Divide by four. Pay that each quarter. Done.

The appeal is that it requires zero forecasting. You’re not projecting Q3 revenue in June or guessing whether that big client will actually pay on time. You’re using a number that already exists on a form you already filed.

The current-year estimate requires projecting your total 2026 tax liability and paying 90% of it across four installments. This makes sense if your income dropped significantly from last year, because the safe harbor would have you overpaying based on a year you’re not repeating. The downside is accuracy. Estimating annual income for a business with seasonal revenue or clients who pay on their own mysterious schedule is speculative at best.

The decision is usually straightforward: income stable or growing, use the safe harbor. Income down significantly, use the current-year method. Income wildly variable, ask your CPA about the annualized income installment method. It’s more work, but it matches payments to actual quarterly earnings.

Whichever method you pick, build a five-minute quarterly check-in around each payment. Pull year-to-date profit, compare it to your projection and adjust if the numbers have moved. The IRS doesn’t require equal payments. It requires adequate ones.

👉 IRS Publication 505: Tax Withholding and Estimated Tax →

The Deep Dive

📊 Safe harbor, annualized income and the penalty rules

The estimated tax penalty is one of those tax code details most business owners discover retroactively, usually as an unexpected line item on their return. It’s not dramatic. It’s just money — $200 here, $600 there — charged because a quarterly payment was late or short. And because it’s calculated per quarter, overpaying in Q4 doesn’t erase what you owed in Q2. The IRS does not grade on a curve.

How it works: The penalty under IRC §6654 is interest on the underpaid amount for each quarter, calculated from the due date until payment or April 15, whichever comes first. The rate — the federal short-term rate plus 3 points — has been running 7% to 8% annualized recently.

How to avoid it: You won’t owe a penalty if your payments equal or exceed the lesser of 90% of your current-year liability or 100% of your prior-year liability (110% if AGI exceeded $150,000). The prior-year safe harbor is the default for most businesses because it requires no forecasting — just last year’s return and a calculator.

The annualized income method is worth knowing if your revenue is highly seasonal. Instead of four equal payments, you calculate each quarter’s installment based on income actually earned during that period using Schedule AI of Form 2210. The math is more involved, but for businesses whose revenue swings 30% or more between quarters, it can significantly reduce penalties.

A few other outs: No penalty applies if your total tax owed is under $1,000. The IRS can waive penalties for casualty, disaster or reasonable cause. And retirement after age 62 or disability during the tax year may qualify for relief.

The strategy is choosing your method before Dec. 31, not after. Retroactive penalty math is expensive math.

👉 IRS Form 2210: Underpayment of Estimated Tax →

Freebie

📋 The 2026–2027 quarterly tax calendar and estimated payment worksheet

Every federal estimated tax deadline through January 2028, state-level quarterly notes for the most common filing states, a built-in estimated payment calculator using both the current-year and prior-year safe harbor methods and a quarterly review checklist. The calendar your accounting software should have come with but didn’t.

Download the Free 2026–2027 Quarterly Tax Calendar →