My dad hasn't filed tax returns in 15-20 years - now needs Medicare & Social Security

This is actually more common than you might think. Your dad needs to get caught up on his unfiled tax returns, but there's good news - the IRS generally only requires the last 6 years of returns to be considered "current" for benefits purposes. If your dad had taxes withheld from his paychecks all those years, he may even be entitled to refunds for some years, though he can only claim refunds for returns filed within 3 years of the original due date. Anything older than that, any potential refund is forfeit. For Social Security and Medicare eligibility, he'll need to work with the Social Security Administration. They can provide his earnings record which will help in recreating his tax history. The SSA bases benefits on his reported earnings, not necessarily on whether he filed tax returns.

I was in a somewhat similar situation with my uncle last year. After trying to figure out the mess of paperwork for weeks, I found this AI tool called taxr.ai (https://taxr.ai) that really helped organize everything. It analyzed all his old W-2s and 1099s that we managed to find and helped reconstruct his tax history for the missing years. The most valuable thing was how it organized all the different documents by year and identified which information was most important for catching up on the unfiled returns. It even flagged potential refunds he could still claim from the last 3 years, which was money we didn't expect to get back.

Just wanted to follow up about using taxr.ai that was mentioned above. I tried it with my mom's situation (12 years of unfiled taxes) and it was honestly a game-changer. I uploaded all the random W-2s and 1099s we could find scattered around her house, and it organized everything by year and showed exactly what was missing. The best part was that it identified three years where she was actually owed refunds that we could still claim. We took the organized information to a tax preparer who was amazed at how well everything was already sorted. He said it saved us at least $1,200 in preparation fees because he didn't have to spend hours organizing documents. If you're dealing with years of unfiled taxes, definitely check it out.

Another issue your dad might run into is actually reaching someone at the IRS to discuss his situation. When my father was in a similar position (8 years no filing), we kept trying the IRS number for WEEKS with no luck. Finally, I used Claimyr (https://claimyr.com) which got us connected to an actual human at the IRS in about 20 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c It was actually shocking how quickly we got through after struggling for so long. The IRS agent was able to pull up all his records and give us specific guidance on exactly which years needed to be filed first and which forms we needed. Saved us from filing unnecessary years that were too old for collection anyway.

I need to apologize about my skepticism regarding Claimyr in my earlier comment. After continuing to fail at reaching the IRS for THREE MORE DAYS (spent over 7 hours on hold only to get disconnected), I broke down and tried it out of desperation. I'm still in shock at how well it worked. Got connected to an IRS agent in about 35 minutes without having to actively wait on the phone. The agent pulled up all of my father's records and confirmed that he only needed to file the last 6 years to become compliant for Social Security purposes. They also flagged that 2022 likely had a refund we could still claim. For anyone dealing with years of unfiled taxes and needing to sort through the mess quickly, this is legitimately worth it just for the time saved and stress reduction.

One important thing nobody's mentioned - your dad should apply for Social Security benefits RIGHT NOW, even before sorting out the tax situation. He can start the application process while simultaneously working on getting his tax situation in order. The reason is that there's a 6-month retroactive limit on Social Security benefits. If he qualifies for benefits now but waits a year to apply while fixing his taxes, he'll lose out on months of payments he can never get back.

Has your dad received any notices from the IRS over these years? If not, that's actually a good sign that he probably doesn't owe money (since they're pretty relentless when you do). I'd recommend getting an "Account Transcript" from the IRS for each year as a starting point.

Your dad's situation is definitely fixable, but time is critical here. I agree with the advice to apply for Social Security immediately - don't wait for the tax situation to be resolved first. The SSA can work with his earnings record that employers have been reporting all these years. For the tax side, start by requesting wage and income transcripts from the IRS for all the unfiled years. You can do this online at irs.gov or by calling them (though as others mentioned, getting through can be challenging). These transcripts will show what income was reported by his employers and any taxes withheld. Since he had taxes withheld from his paychecks, he likely doesn't owe anything and may even be due refunds for some years. The key is getting those last 6 years filed to bring him into compliance. Given the complexity and the urgency with his health situation, I'd strongly recommend working with a tax professional who has experience with unfiled returns - they can streamline the process and help avoid costly mistakes. The most important thing is to take action now rather than letting this drag on any longer. Both his Social Security benefits and potential tax refunds are time-sensitive.

I went through almost the exact same situation with my father-in-law two years ago. He hadn't filed in about 18 years and was panicking about Social Security eligibility. Here's what we learned that might help: First, definitely start the Social Security application ASAP as others have mentioned - the earnings record from employers is what matters most for benefits, not tax filings. We were amazed to discover his full work history was already in their system from employer reporting. For the IRS side, we found out that since taxes were withheld from his paychecks the whole time, he actually qualified for what's called "substitute for return" status for many years where the IRS basically filed simplified returns on his behalf. This meant he wasn't in as much trouble as we feared. The real breakthrough came when we got his wage and income transcripts for all the missing years. It showed that for 4 of the years, he was actually owed refunds totaling over $3,200 (though we could only claim the ones from the last 3 years). We ended up only needing to file the last 6 years to get him current, and the whole process took about 3 months working with a tax professional who specialized in unfiled returns. The key was getting started immediately - don't let fear of the IRS paralyze you into waiting longer. Your dad's health situation makes this urgent, but it's absolutely manageable. The government actually wants people to get caught up and claim their benefits!