Q2 Estimated Tax Payments: What Rochester Self-Employed Workers Need to Know Before June 15

For most people, tax season ends on April 15.

For the self-employed, freelancers, and small business owners in Rochester and Greece, NY, taxes don’t end — they just shift into a different rhythm.

One of the most important dates in that rhythm is June 15.

That’s the deadline for the second quarterly estimated tax payment of the year, and it sneaks up on a lot of people every June.

Missing it can lead to penalties, interest, and an unnecessary headache later in the year. The good news is that getting it right isn’t complicated — you just need to understand what’s actually being asked of you.

What Are Estimated Tax Payments?

When you’re a traditional employee, your employer withholds taxes from each paycheck.

By the time you file in April, most or all of your tax liability has already been paid in.

When you’re self-employed, that withholding doesn’t happen.

Instead, the IRS expects you to pay your taxes throughout the year in four quarterly installments. These are called estimated tax payments.

They cover both your federal income tax and your self-employment tax (which funds Social Security and Medicare).

Who Has to Make Estimated Payments?

Estimated payments aren’t just for full-time freelancers.

You generally need to make them if you expect to owe at least $1,000 in federal taxes for the year and your withholding won’t cover it.

This commonly applies to:

• Self-employed workers and freelancers across the Rochester area
• Small business owners (sole proprietors, partners, S-corp shareholders)
• Landlords with Monroe County rental income
• Anyone with significant investment or capital gains income
• People with side income that doesn’t have taxes withheld

If any of those describe you, the June 15 deadline applies — both at the federal level and for New York State.

The 2026 Quarterly Deadlines

Estimated tax payments don’t actually fall in even three-month chunks, which surprises a lot of people.

Here’s the schedule:

• Q1: April 15 (covers Jan–Mar)
• Q2: June 15 (covers Apr–May)
• Q3: September 15 (covers Jun–Aug)
• Q4: January 15 of the following year (covers Sep–Dec)

Notice that Q2 only covers two months — April and May. That shorter window is one reason this deadline catches people off guard.

What Happens If You Miss It

The IRS doesn’t send a friendly reminder when you miss an estimated payment.

Instead, you accumulate an underpayment penalty, calculated on how much you should have paid and how long you took to catch up.

It’s not a flat fee. It’s essentially interest charged on the underpayment, and it can build over the rest of the year.

Even if you pay everything you owe at the April filing deadline, missed quarterly payments can still result in penalties on your return.

The penalties aren’t catastrophic for most people, but they’re entirely avoidable — which makes them frustrating to pay.

How to Calculate What You Owe

There are two common approaches.

1. Base it on last year’s return. If you pay in 100% of last year’s total tax liability across your four estimates (110% if your income was over $150,000), you’ll generally avoid an underpayment penalty regardless of how this year actually shakes out. This is called the “safe harbor” method.

2. Project this year’s income. If your income has changed significantly — up or down — you can estimate this year’s liability directly and pay 25% per quarter.

The right approach depends on how stable your income is and how much detail you want to track.

Why Q2 Is Especially Easy to Miss

The April 15 deadline is hard to forget. Everyone is talking about taxes, you’re likely filing your return, and the calendar is loud.

By June, most of that has gone quiet.

That’s exactly why so many self-employed taxpayers in Rochester, Greece, and the surrounding Monroe County communities miss it.

Add in summer schedules, vacations, and the fact that the Q2 window is shorter, and it’s easy to look up in late June and realize the deadline came and went.

Setting a calendar reminder a week or two ahead is one of the simplest ways to avoid this.

How to Make a Payment

The IRS gives you a few options:

• IRS Direct Pay — free, direct from your bank account
• EFTPS (Electronic Federal Tax Payment System) — the IRS’s official scheduling tool, useful for setting up the full year in advance
• Debit or credit card — processing fees apply
• Mail with Form 1040-ES — still allowed, but slower

If you have a New York State income tax liability as well, you’ll need to make a separate state estimated payment through the New York State Department of Taxation and Finance.

It’s easy to forget the state side, and the penalties stack up the same way.

Common Estimated Tax Mistakes We See

A few patterns come up year after year with our Rochester and Greece NY clients:

• Forgetting that self-employment tax is part of the calculation, not just income tax
• Underestimating how much side income has grown over the year
• Paying federal estimates but forgetting the New York State piece
• Skipping a quarter and trying to make up for it at the end
• Pulling money out of business accounts without setting tax dollars aside

Each one is fixable. Each one is also easier to avoid than to clean up later.

How a CPA Helps With Estimated Payments

This is one of those areas where having a CPA in your corner pays for itself.

Instead of guessing what to send in, you’re working from a real projection based on your actual income, expenses, and life situation.

That means:

• No surprise penalties
• No overpaying and tying up cash unnecessarily
• No scrambling at the end of the year to make up for missed quarters

Through our tax services, we help Rochester and Greece NY self-employed workers and small business owners stay ahead of every quarterly deadline — including the one most people forget.

Planning Ahead for Q3 and Q4

If you’re paying attention to Q2, this is also a good moment to look ahead.

The Q3 deadline is September 15. Q4 is January 15.

For a lot of Western New York self-employed clients, setting up a simple system now — whether that’s automatic withdrawals, calendar reminders, or a quick mid-quarter check-in with your CPA — takes the stress out of the rest of the year.

Estimated taxes don’t have to feel like a constant scramble. With a little structure, they become routine.

The Bottom Line

June 15 is one of those quiet deadlines that has a loud impact if you miss it.

The good news is that catching it doesn’t require complex planning. It just requires knowing it’s there and having a number you can confidently send in.

If you’ve never made an estimated payment before, or you’re not sure if your number is right, this is a great moment to get a second set of eyes on it.

Not Sure What You Owe for Q2?

If you’d like help calculating your estimated payment or setting up a system that keeps you on track all year, we’re here.
Contact us and we’ll walk through your situation together.

Disclaimer: This article is for informational purposes only and should not be considered tax, financial, or legal advice. Individual circumstances vary. Always consult a qualified professional regarding your specific situation.