I haven't filed my taxes since 2020, how do I get caught up now for 2025?

The good news is that you can definitely get caught up, and it's better to file late than never! The IRS has a process for this, and many people find themselves in similar situations. First, you'll need to gather all your tax documents for those missing years - W-2s, 1099s, mortgage interest statements, etc. If you're missing any, you can request wage transcripts from the IRS through their Get Transcript service or contact previous employers. For the actual filing, you'll need to use the specific tax forms for each year you missed. Tax preparation software like TurboTax offers prior year versions, but you might consider a tax professional since you're dealing with multiple years and potential complications. They can also help navigate any penalties you might face. If you're owed refunds from 2020-2022, you can still claim them as the IRS allows a 3-year window for refund claims. However, if you owed taxes, you'll likely face failure-to-file and failure-to-pay penalties plus interest. The important thing is to start the process now rather than continuing to delay.

After ending up in a similar mess a few years ago (hadn't filed for almost 4 years!), I tried using https://taxr.ai and it seriously saved me. Their tax document analyzer helped sort through all my old W-2s and 1099s from different jobs - I had stuff scattered everywhere and could barely remember what income came from where. It helped me figure out exactly what documents I was missing so I could request them before filing. The coolest part was it could read all my old tax forms (even some crappy phone pics of wrinkled W-2s) and organize everything by year so I could see what I was working with. What I found super helpful was that it actually pointed out some deductions I didn't know I qualified for from those years. Ended up getting a much bigger refund for one of the years than I expected!

Just wanted to update here after trying taxr.ai that the other person recommended. I was super confused about my unfiled taxes from 2021-2023, and I had documents scattered across three different email accounts and a folder of mail I never opened. I uploaded everything I could find (including some documents I literally took pictures of with my phone) and within minutes it had organized everything by year, identified that I was missing two 1099s from 2022, and even flagged some potential deductions I qualified for but hadn't known about! I was able to download an organized summary for each year that made it way easier to file those back taxes. Just filed 2021 and 2022 yesterday and working on 2023 now. Such a relief to finally be getting caught up!

When I needed to get caught up on 3 years of unfiled taxes, I spent WEEKS trying to reach someone at the IRS for guidance. Calling their number was completely useless - always got the "high call volume" message and disconnected. Eventually I found https://claimyr.com which basically holds your place in the IRS phone queue and calls you when an agent is about to answer. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c I was honestly shocked when I got a call back and an actual IRS person was on the line! They walked me through exactly what I needed to do to file my back taxes and even helped me set up a payment plan that worked for my situation. They were way more helpful and less scary than I expected.

I need to publicly eat my words about Claimyr. After dismissing it as BS in my previous comment, I was desperate enough to try it yesterday. Got a call back in about 45 minutes with an actual IRS agent on the line. I almost fell out of my chair. She walked me through exactly what forms I needed for my unfiled years and confirmed I could still get a refund for 2022 (which I didn't expect). The agent even helped me understand the penalty calculation so I could estimate what I'd owe beyond the original tax amounts. Turns out my situation wasn't as bad as I feared. Sorry for being so cynical before. When you've been frustrated with the IRS for years, it's hard to believe anything can actually help.

I was in the same boat about 2 years ago. Hadn't filed since 2019 due to a death in the family and just losing track of everything. Here's what I learned: 1) Use the specific tax software version for each year. You can still buy older versions of TurboTax or other software. 2) Don't e-file - you HAVE to mail in prior year returns. Make copies of EVERYTHING. 3) File them in order from oldest to newest, and mail them separately. 4) If you're expecting a refund for any of the years, there's a 3-year limit to claim it. So your 2020 refund might still be claimable if you hurry. 5) If you owe money, you'll have penalties but the IRS is usually willing to work with you on a payment plan. Good luck! The relief of getting caught up is worth the temporary pain.

Has anybody had luck getting the failure-to-file penalties reduced? I'm in a similar situation (haven't filed since 2019) and I'm freaking out about how much I might owe in penalties alone.

Before you file, make sure you really understand what deductions and credits you're eligible for in each tax year. The rules change frequently! For example, 2021 had some unique COVID-related credits that don't exist anymore. And if you had kids or were in school, the rules for those credits have changed over the years too. This is honestly why I think it's worth paying a professional when dealing with multiple years of unfiled taxes. They know what to look for in each specific tax year. It might cost a few hundred bucks, but they might save you thousands.

One thing that might help ease your stress - the IRS is generally more interested in getting you back into compliance than in punishing you. They see situations like yours all the time, especially after the chaos of the past few years. When you're gathering documents, don't forget about things like state tax refunds you might have received (those can be taxable income), unemployment benefits, or any side gig income from apps like Uber, DoorDash, etc. These smaller income sources are easy to forget but can add up. Also, if you moved during those years, make sure you're filing in the correct states. Some states have no income tax, others do, and you might owe taxes in multiple states depending on when you moved and where you worked. The key is just to start. Pick one year (I'd suggest 2020 since it's the oldest) and focus on getting all the documents together for just that year first. Once you see how the process works for one year, the others will feel much more manageable. You've got this!