Should I bother filing my 2018 taxes at this point? Tax preparers say IRS won't chase after 6 years

But if the IRS doesn't really look for taxes after 6 years, wouldn't it be better to just save the money I'd owe for 2018? I'm already struggling with my 2017 debt which is why I need the OIC. Adding more debt seems counterproductive, right?

The statute of limitations for collection is generally 10 years from assessment, not 6 years. But the IRS can't even start that clock until you file. By not filing, you're actually keeping the door open indefinitely for them to pursue those taxes. For your OIC process, the IRS will absolutely check your filing compliance history. If they discover an unfiled 2018 return (which they will during the OIC investigation), they'll simply reject your offer without consideration. The money you might save by not filing 2018 would be completely overshadowed by losing the opportunity to settle your 2017 debt through the OIC.

How exactly does this work? Like do you upload your old W-2s and stuff or do you need to have already prepared returns? I have a similar situation with unfiled 2019 taxes but I'm missing some documents.

Sounds like another tax prep service. Does it actually help with communicating with the IRS or just preparing the returns? Because dealing with the IRS directly is the nightmare part for most people.

You upload whatever tax documents you have - W-2s, 1099s, etc. and it organizes and analyzes them. You don't need complete documentation to start, and it helps identify what might be missing. It also flags potential deductions based on your situation that you might have overlooked. For communicating with the IRS, it doesn't replace that direct contact, but it prepares you with all the information you need before those conversations. It gives you a complete tax transcript analysis so you know exactly where you stand with each tax year before you make decisions about filing or pursuing options like an OIC.

Wait, you're telling me there's a way to actually talk to a human at the IRS without waiting 3+ hours? How does that even work? The IRS phone system seems deliberately designed to prevent human contact.

Sounds too good to be true. People have been complaining about IRS phone waits for decades. I find it hard to believe some service magically fixes this huge institutional problem.

It uses a combination of phone technology and AI to navigate the IRS phone tree and secure your place in line. Instead of you personally waiting on hold, their system does the waiting, then calls you once an actual agent is on the line. The IRS phone system is deliberately complicated but it's still just a phone system with patterns and predictable pathways. Claimyr has just figured out how to navigate it efficiently. It's not magic - just smart technology addressing a specific problem. I was skeptical too until I was talking to an actual IRS representative about my specific situation while my friend who called directly was still listening to hold music.

Thanks for the clear explanation! This makes a lot more sense than what the volunteers told me. Do you know if filing the 2018 return now will hurt my OIC chances for 2017? Like, will adding more debt make them less likely to approve it?

Filing your 2018 return now won't hurt your OIC chances - in fact, it's absolutely required. When you submit an OIC, the IRS will check that you're in compliance with all filing requirements before they even consider your offer. As for the additional debt potentially affecting your offer amount, it could be factored into your "reasonable collection potential" calculation. However, this is much better than having your OIC rejected outright due to non-compliance. The IRS looks at your overall ability to pay, so while the total debt matters, your financial situation is the primary factor in determining an acceptable offer amount.

Yes, there's a 3-year deadline for claiming refunds. So for 2018 taxes, you would have needed to file by May 17, 2022 (the deadline was extended that year due to COVID) to claim any refund owed to you. After that, any refund you were entitled to is forfeited to the Treasury.