How I managed to prolong my 2025 tax-year ordeal
Normal people had their 2025 federal taxes filed no later than April 15. Abnormal people–to be nicer about it, those with more complicated tax scenarios or who succumbed to cognitive overload in early April–filed for a free six-month extension and paid what they estimated they owed by April 15, then completed the rest of their tax-prep tasks by Oct. 15.
And then there was me.
Despite years of practice at filing for an extension and using that bonus time to get my returns right–it’s become all but a default setting over 15-plus years of freelance life–I needed two extra days to conclude my 2025 federal tax year.
I knew things would be more complicated this year because of Intuit–specifically, the TurboTax developer removing support for the business-essential Schedule C from its “Do It Yourself” tier and instead asking me to pay $199 for an “Expert Assist Premium” offering that would have almost doubled my costs over last year’s.
I was already salty at the company for its history of trying to stop governments from competing with TurboTax, including bitter resistance to the IRS launching its Direct File app1 under the Biden administration. So I decided to take my business elsewhere and opted for FreeTaxUSA, an Editors’ Choice pick at PCMag.
Per the name, this service of Provo, Utah-based TaxHawk charges nothing for federal returns–even those complicated by investment and small-business income–and charges just $15.99 for state returns2.
For the most part, FreeTaxUSA proved to be an adequate replacement for TurboTax. It made three mistakes when scanning PDFs of tax forms that I’d uploaded and balked at doing anything with a fourth, but those glitches–in areas where I’d want to double-check the numbers recorded anyway–were easy enough to fix.
I also found it weird that FreeTaxUSA didn’t suggest how much to contribute to my SEP (Simplified Employee Pension) IRA to minimize my tax bill. But since I had decided to step through my returns in TurboTax in a separate window to be sure I didn’t miss anything–which I’m not saying is a great life choice for everyone–that was easy enough to fix.
This extra work ensured that I’d need to file an extension, so I once again did that and then behaved as foolishly as ever by ignoring both apps until early October. An evening of work last weekend revealed some inconsistent Sched C data entry that, when fixed and even after triple-checking, left me owing slightly less in FreeTaxUSA’s math than in TurboTax’s.
Just in case, I decided to wait until Thursday, after returning from a brief work trip to Dublin, to give my return one final look before e-filing it via FreeTaxUSA. I clicked the “Send Tax Return” button with several hours to spare…. and then got an e-mail that I did not expect or enjoy: “Action Needed! Your 2025 Federal Tax Return Was Rejected.”
That message offered two explanations that conflicted somewhat: Either “the Social Security number or last name entered for a dependent doesn’t match their records” or “a dependent’s Social Security number has already been used as a dependent on another return for the 2025 tax year.”
The first possibility could not possibly be true, I thought, while it seemed quite plausible that our kid had joined us in being a victim of a data breach. I dug into the IRS help page on this topic and saw that it cited the same two reasons and advised that if I had the dependent SSN correct, I could e-file again after adding an Identity Protection Personal Identification Number (IP PIN) to my account.
But when I tried to create an IP PIN Thursday evening, the IRS site reported a “partial outage” that locked out that option. It was then too late to call; phone support only runs from 7 a.m. to 7 p.m. on workdays3.
If you’ve been reading this and thinking “why didn’t this bozo double-check his kid’s SSN?”: I did, ineffectively. With jet lag now fogging my head, I did not notice that the final four digits only had three of the right numbers, only one of which was even in the right position. Stupid, I know.
Having also learned that the IRS allots a five-day “Transmission Perfection Period” to correct a rejected e-file attempt, I gave up Thursday night.
In the middle of a work-clogged Friday, I set an IP PIN on my account and saw that it, too, didn’t fix things… and then finally, on Saturday I thought to reach again for the folder in the filing cabinet holding everybody’s important documents.
That revealed that I, accounting genius, had our teenager’s SSN wrong in the return and in the secure note in 1Password from which I’d copied those nine digits months ago.
I fixed that, and the e-file sailed through. Then I sent a text to my wife reporting this success, followed by this self-eval: “don’t I feel like a dumbass now!”
This is one of my more embarrassing cases of user error, but if I document it maybe somebody else won’t make the same smooth-brained mistake. This has also reminded me, somewhat painfully, that any important number is worth double-checking–especially if, like me, you’ve caught yourself transposing digits often enough to wonder if you’ve had dyscalculia all along.
- The Trump administration killed off Direct File last year, and I don’t think Intuit mourned its demise. ↩︎
- As much as I hate the idea of paying anybody to file Virginia’s relatively simple state income tax returns–the commonwealth being an early sucker for Intuit’s crony-capitalist lobbying–filing our 2024 state taxes on paper became a bureaucratic odyssey that I don’t want to repeat. ↩︎
- DOGE cuts whacked the IRS workforce, but its phone-help hours were the same in 2024. ↩︎