For those of you glued to your screens last week watching Ed the zebra make his way through neighborhoods and highways in Tennessee, I’m happy to report: he has been found and returned safe and sound to his owner.
Now you can return back to your regularly scheduled summer activities. (June 20th is the official first day of summer, but I think we can all agree that it’s time to make the transition, if you haven’t already.)
And I’m guessing you’re more focused on sitting poolside and juggling summer camp pickups than your taxes. (Totally fair.) If you filed an extension back in April, it’s easy to slip into that I’ve-got-until-October mindset and forget about it until the leaves start turning.
Yes, October 15 feels far away… but it’ll be here before you know it. And waiting until the last minute (again) doesn’t just create stress — it also closes the window on big-picture tax strategies (which is where the real savings begin).
Now, the good news? If you’re already one of my Milwaukee clients and we filed an extension for you, I’m watching the calendar so you don’t have to. That’s what having a tax pro in your corner is all about – you get to enjoy your summer, and we do the work of making sure you get things squared away in a timely way.
But we do need to make sure you get us the rest of your tax documents well ahead of time, so we can do this right.
If we haven’t worked together yet, this is a great time to get on my list:
https://nealgroup.net
I share strategies like this regularly with my Southeastern Wisconsin clients to help them not only file on time but plan smarter going forward.
But first — let’s get into what you need to do now so that tax extension doesn’t become another last-minute scramble (and so you aren’t piling up penalties and interest if you owe)…
Jon Neal’s 6 Steps to Making the Tax Extension Filing Deadline
“Sometimes life gives you a second chance… It’s what you do with those second chances that counts.” —Dave Wilson
If you missed the April 15 tax deadline this year, filing an extension was absolutely the right move. It bought you time — not to procrastinate, but to get your return filed correctly, completely, and in a way that could potentially save you money.
But here’s the thing: that extension doesn’t put the IRS on pause. The clock is still ticking. And October 15 will be here before you know it. If you’re not careful, you could end up compounding the problem — facing penalties, interest, or leaving valuable deductions on the table.
I’ve seen it too often: Milwaukee clients come in mid-October with a shoebox of papers (and a lot of stress). And in many cases, a little earlier planning would have saved them time, money, AND headaches.
So, let’s talk through what you need to do now to avoid being that person — and use this extra time to your advantage.
What’s the tax extension filing deadline?
Your new filing deadline is October 15, 2025. Unless you’re a U.S. citizen living abroad — in which case, June 17, 2025, is your deadline to file or request a four-month extension. (Note: your payment deadline was still April 15, just like everyone else.)
And if you were impacted by a federally declared disaster this year? You might have more time — but you’ll need to check your eligibility. IRS disaster relief extensions can vary a lot by state and situation.
What the tax extension filing deadline ISN’T for
Let’s clarify something: the extension gives you more time to file, but not more time to pay. That deadline (again) was April 15. So if you owed the IRS, you’ve been accruing interest and penalties since then.
The IRS expects you to have made a reasonable estimate and sent in what you could.
Now, if you paid at least 90 percent of what you owed by April 15, you might dodge some of that penalty… but only if you file your completed return by the tax extension filing deadline. So, let’s help you make that happen…
7 steps to stay ahead of the tax extension filing deadline
Step 1: Gather your documents. Keep a running checklist of what you have and what’s still missing (if you need a checklist, I’ve got one handy under Resources). And don’t just rely on the documents you think you should have. Pull transcripts from the IRS (like the wage and income transcript) to catch forms you may have forgotten or that were issued late — especially if you’ve moved, changed jobs, or had investments.
Step 2: Review last year’s return. Doing this helps you catch deductions, carryovers (like capital losses, charitable contributions, or education credits), and income sources that are easy to miss — and gives you direction to prepare this year’s return accurately.
Step 3: Make your April payment. If you made a payment with your extension, make sure it’s entered on your return. Forgetting this is one of the most common causes I see of IRS “balance due” confusion.
Step 4: Prep now. Don’t wait until you have everything. Get as much of your return done now as you can, while the info is fresh. If you’re just missing one or two pieces, leave placeholders and finish the moment they come in. You’ll have valuable time to fix mistakes or plan for payments if you have a surprise balance due.
Step 5: Make an estimated payment (if needed). If you realize you underpaid in April, send in another payment now (IRS Direct Pay makes this easy). Even without a completed return, it’ll help reduce late-payment penalties. And it signals good faith to the IRS.
Step 6: Check your state. State deadlines and rules vary – and in some cases, your extension doesn’t apply unless you also submitted a state extension form. And remember: states can be less forgiving than the IRS when it comes to late penalties.
Step 7: Factor in life changes. Did you get married or divorced this year? Have a child? Start a side business or inherit assets? These kinds of life events trigger tax changes — and now’s the time to account for them before you file.
Your tax extension is a unique opportunity to really dial in your tax strategy. Yes, filing an extension gave you extra time — but that October 15th deadline is still a firm one. So, it’s important you use this window wisely: Get organized and filing-prepared NOW. The earlier you prep, the more options you have to minimize penalties, adjust for underpayments, and file a clean return.
Let’s not let this extension slip into procrastination. Use this window to your advantage. Let us help you walk into October with your return ready – or, better yet, filed. Not sure what your next best step is right now? Just grab a time on my calendar, and we’ll map it out together:
To second chances,
Jon Neal