If You Filed an Extension and Still Haven't Filed, Now Is the Time to Figure Out What's Keeping You From Finishing.
If you filed an extension back in April, you bought yourself six more months to get your return filed. You now have one month left.
If your return still isn't done, now is a good time to figure out what's actually keeping you from finishing.
Maybe you're missing documents. Maybe you're self-employed and your records aren't together. Maybe something on the return genuinely has you stumped. Maybe you think you're going to owe and you've been avoiding filing because you can't afford to pay it. Or maybe you've just been putting it off because taxes are unpleasant and April became May, May became June, and suddenly it's September.
Those are different problems, and they don't all have the same solution.
Let’s make sure this is clear: an extension gave you more time to file your return. It did not give you more time to pay. If you owed federal income tax for 2025, that payment was generally due April 15.
So if the reason you haven't filed is because you know you can't pay the whole balance, waiting to file doesn't solve that problem. Get the return filed, then deal with the balance. The IRS has payment options for people who can't pay everything at once.
If you're missing a W-2, 1099, or another tax document, start there. Contact whoever issued it and ask for another copy. You can also pull your Wage and Income Transcript from the IRS to see much of the income information that was reported under your Social Security number. Some identifying information is masked on the transcripts you can access yourself, so they may not give you everything you need to electronically file, but it’s a solid start.
A tax professional with the proper authorization can access more complete transcript information through the IRS. If missing documents are the only thing keeping you from filing, getting help gathering the information doesn't necessarily mean paying someone to prepare the return.
If you're self-employed and your records are the problem, you've still got time to start untangling them. Figure out what came in. Start sorting through what went out. Pull bank and credit card statements. Gather receipts. You don't need to solve the entire year in one sitting. You need to start turning a pile of information into something you can actually use.
And sometimes there isn't a missing document or complicated tax question. You've just been putting it off. April became May. May became June. You know the rest.
No lecture. But now you know what the problem is.
If something on the return genuinely has you stuck, now is also a much better time to ask for help than October 14. That doesn't necessarily mean handing the entire return over to somebody. You may need someone to prepare it. You may need help figuring out what you're missing. Or you may find that once everything is in front of you, you can finish it yourself.
You bought yourself six months. Use the month you have left to figure out what the roadblock is and do something about it.
Stay Sharp. 🗡️
-VH
Filed an extension?
For most individual taxpayers who timely requested an extension, the deadline to file your 2025 federal return is October 15, 2026. Remember, an extension gives you more time to file, not more time to pay.
https://www.irs.gov/forms-pubs/extension-of-time-to-file-your-tax-return
Missing a W-2, 1099, or other tax document?
Start by contacting whoever issued it. You can also pull your IRS Wage and Income Transcript to see much of the income information reported to the IRS. Some identifying information is masked on transcripts you access yourself, so you may still need the original documents or help obtaining more complete information.
https://www.irs.gov/individuals/get-transcript
Think you owe but can't pay it all at once?
Don't let the balance keep you from filing the return. The IRS offers payment options for taxpayers who can't pay what they owe in full.
https://www.irs.gov/payments/payment-plans-installment-agreements
Self-employed and trying to get your records together?
The IRS doesn't require one particular recordkeeping system. Your records should clearly show your income and expenses and support the amounts reported on your return.
https://www.irs.gov/businesses/small-businesses-self-employed/recordkeeping
Need to file your return?
If you've figured out what's been holding you up and you're comfortable preparing the return yourself, I've personally found FreeTaxUSA* to be one of the easiest self-filing options to use. Federal returns are free, and state returns are available for an additional fee.
*No affiliation or sponsorship. I just don't think you should have to pay to e-file a return you can prepare yourself. It's what I've used myself and recommended to friends and family.
