Most contractors think of taxes as an April thing. You file, you exhale, you get back to work. But if you run your own business, there’s another date that matters just as much, and it’s coming up fast. June 15 is the deadline for your second-quarter estimated tax payment.
If that sentence made your stomach drop a little, stick with me. This is simpler than it sounds, and once you understand it, it stops being scary.
What an estimated payment actually is
When you work a W-2 job, taxes come out of every paycheck automatically. When you run a roofing crew or any other business, nobody’s withholding for you. So the IRS asks you to pay your taxes in four chunks across the year instead of all at once. Those chunks are called estimated payments. The June 15 payment covers the income you earned in April and May. It’s not a bill someone mails you. It’s on you to send it.
Who actually owes it
Not everyone does. As a general rule, if you expect to owe a meaningful amount when you file next spring, the IRS wants you paying in along the way. For a lot of self-employed contractors, that’s the case. If you took a W-2 job part of the year, or your spouse’s withholding covers most of the household, your situation might be different. This is exactly the kind of thing worth a five-minute conversation rather than a guess. Guessing is how people either overpay and float the government an interest-free loan, or underpay and get a penalty.
How to ballpark a safe number
Here’s the part most people overcomplicate. You don’t need a perfect number by June 15. You need a reasonable one. A common approach is the “safe harbor” idea: pay in at least as much as your total tax from last year, spread across the four quarters, and you’re generally protected from an underpayment penalty even if you end up owing more. So if you know what last year’s tax came to, a quarter of that is often a solid starting point. If this year is shaping up very different, busier season, bigger jobs, a new truck you wrote off, the number shifts. That’s where having someone look at your actual books helps. But please don’t let “I’m not sure of the exact amount” turn into sending nothing.
Three ways to actually pay it
Once you have a number, paying is the easy part. You’ve got three real options:
1. IRS Direct Pay. Free, online, straight from your bank account at irs.gov. No account to set up. You’ll pick “estimated tax” and the 2026 tax year. Fastest way for most people.
2. EFTPS. The Electronic Federal Tax Payment System. A little setup the first time, but if you like every payment in one place, business owners tend to prefer it.
3. By mail. You can still send a paper check with a 1040-ES voucher. Give it enough lead time, and the postmark matters.
Montana has its own estimated payment process for state income tax, separate from the federal one. If you owe at the state level too, that runs through the Montana Department of Revenue. We help clients line both up so nothing slips.
The mistake that actually costs you
The expensive move isn’t paying a little wrong. It’s ignoring the date entirely, then getting hit with a penalty on top of the tax you owed anyway. That penalty is pure waste. It buys you nothing. The second most expensive move is overpaying out of fear, sending way more than you need because you’d rather be safe, and starving your own cash flow during your busiest season. Neither one is necessary.
If you’d rather just hand it off
If you’d rather just hand it off, I get it. I set up estimated payments for Montana trades every quarter. I’ll look at where you actually stand, give you a number you can trust, and make sure June 15 comes and goes without a surprise. Fixed fee, no lecture about last quarter. If you want that off your plate before the 15th, call me at (406) 609-4567 or book a free consultation. The earlier in the month you reach out, the easier it is to get it right.