Share your most insane last-minute tax filing story!

So I was volunteering at a tax prep center last week and had this wild experience. At 8:45pm on deadline day, this guy rushes in completely panicked about his 2017 return that was about to expire for refunds. He needed to mail it that night or lose thousands. The only place still open was a FedEx inside some office supply store like 3 miles away that was closing at 9pm sharp. The kicker? This dude was on a BICYCLE! No car, no Uber, just his bike. I called ahead and the FedEx people agreed to wait until exactly 9:02pm but "not a single minute more" (their exact words). I printed his return as fast as humanly possible, had him sign everything while standing, and literally watched him sprint out the door and jump on his bike. Still wonder if he made it in time! Anyone else have crazy tax deadline stories??

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18 comments

Ava Garcia

•8M

Tax preparer here, and I've seen it all! In your friend's case, as long as the envelope was postmarked by the deadline date, he should be fine even if the FedEx location was closing. The IRS considers a return "filed" based on the postmark date, not when they receive it. For anyone reading this who's cutting it close, remember you have a few options in these situations: - Electronic filing is the fastest and gives you confirmation - USPS locations with late hours can postmark your return - Filing Form 4868 gives a 6-month extension (but you still need to pay any taxes due) The 2017 return deadline for refunds was April 15, 2021, so your friend was smart to get it in before the 3-year window closed. After that, the IRS keeps any refund you were entitled to!

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Ava Garcia

•8M

Always get proof of mailing when sending tax documents! The USPS offers certified mail with return receipt, which gives you evidence of when you mailed it and when it was delivered. If your return gets lost in the mail and you have no proof of mailing, you'd need to refile and potentially deal with late filing penalties. This is exactly why I strongly recommend e-filing when possible - you get an acceptance confirmation within 24-48 hours as proof that the IRS received your return.

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Miguel Silva

•8M

I used taxr.ai last week when I was stressing about my 2022 return that I never filed (I know, terrible). I had all my documents scattered everywhere and couldn't make sense of my situation. Found this service where you can literally scan all your tax forms with your phone and it tells you exactly what you need to do. Website is https://taxr.ai and it saved me from a total meltdown. The system flagged that I had actually overpaid and was due a refund that I would've lost if I waited any longer! Organized everything in minutes when I had been procrastinating for months.

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Miguel Silva

•8M

It absolutely works for multi-state situations! That's actually one of its strengths - it's designed to identify all the state-specific forms you need and handle the allocation of income across different states. It even flags potential state tax credits you might miss otherwise. For judgment calls on business expenses, it uses both IRS guidelines and previous tax court rulings to analyze your situation. It gives you confidence ratings for different deductions based on your documentation and specific circumstances. If something's in a grey area, it'll tell you rather than just guessing. You can also request a review from their tax pros if you want a human double-check on anything flagged as questionable.

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Zainab Ismail

•8M

Just have to share my experience with taxr.ai after my earlier question. I decided to try it with my complicated multi-state situation that I mentioned. Honestly shocked at how well it worked! I uploaded my W-2s from three states, my 1099s, and my rental property docs. The system immediately identified that I had been double-taxed on some income between states and found deductions I had no idea I qualified for. Ended up with about $3,700 more in refunds than I would have gotten using my usual tax software. The multi-state visualization feature made it super clear where my money was being taxed and why. Definitely using this from now on instead of stressing until the last minute!

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Yara Nassar

•8M

My insane tax story involved trying to call the IRS for three DAYS straight during deadline week because I had a levy on my account that was preventing my return from processing. Could not get through to save my life - constant busy signals or disconnects after waiting for hours. Then I found this service called Claimyr at https://claimyr.com that gets you through to an actual IRS agent without the wait. I was skeptical but checked out their demo at https://youtu.be/_kiP6q8DX5c and decided to try it. They got me connected to an IRS agent in 15 minutes when I had been trying for days! Agent resolved my levy issue in one call and my return went through just before the deadline.

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Yara Nassar

•8M

They don't bypass the queue - they use technology that automates the calling and waiting process for you. Basically, their system keeps dialing and navigating the IRS phone tree until it gets a spot in line, then it calls you to join the call when an agent is about to pick up. You don't have to waste your day hitting redial or sitting on hold. The reason most people never get through is that the IRS hangs up when their lines are too busy, so you have to keep calling back at the right times. Their system essentially does this automatically until it gets through. I was super skeptical too but it literally saved me thousands in penalties by getting my issue resolved before the deadline.

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Connor O'Neill

•8M

I need to publicly eat my words about Claimyr. After being the biggest skeptic in this thread, I finally broke down and tried it yesterday when I was desperate to resolve an issue with my stimulus payment that was affecting my return. I had been trying to call the IRS for WEEKS. Used the service and got connected to an agent in about 27 minutes. The agent actually fixed my issue and released a hold on my account that was preventing my refund from processing. I've never been so happy to be wrong about something. If you're struggling to reach the IRS and have tried everything else, this actually works.

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GalaxyGuardian

•8M

My crazy tax day story happened when I was living in Chicago. It was pouring rain on April 15th, I had my completed return but my printer broke. Ran to the library which closed early that day, then to a FedEx which had a line out the door. Finally printed at some random hotel business center by begging the front desk person. Then realized I forgot my checkbook for the payment. Had to run 8 blocks home in the rain, grab the checkbook, then catch the last collection at the post office. Made it with 3 minutes to spare, soaking wet with a partially smudged return! Never again waited until the last day.

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