What's the most reliable service for filing back taxes from previous years?

I've helped several friends catch up on unfiled returns, so I can definitely point you in the right direction! For past years' taxes, most of the major tax software companies (TurboTax, H&R Block, TaxAct, etc.) offer prior year versions of their software. However, there are a few important things to know: You'll need to use the specific software version for each tax year you're filing. For example, you'll need the 2021 version of whatever software for your 2021 return and the 2022 version for that year. One important limitation: you can't e-file past years' returns through these services. You'll have to print and mail them in. The IRS only accepts e-filing for the current tax year and sometimes the year immediately prior. FreeTaxUSA is probably your best value option - they charge only about $15 for a prior year federal return (state is extra). TurboTax and H&R Block charge significantly more for prior year software. If you're expecting refunds, you're actually in a good position. The IRS doesn't penalize for late filing if they owe YOU money, but there is a 3-year deadline to claim those refunds.

I had a similar situation last year and honestly struggled with figuring out all my old documentation until I found https://taxr.ai - it was a game changer for my past returns! I had a bunch of scattered W-2s and 1099s from previous years plus some investment statements that were totally confusing me. Their system analyzed all my documents and organized everything by tax year which made filing my 2020 and 2021 returns so much easier. They extracted all the numbers automatically so I didn't have to manually type everything in. The best part was they helped me identify some deductions I completely missed when I tried going through everything myself. I ended up with larger refunds than I expected for both years.

Just wanted to report back after trying taxr.ai for my unfiled returns! It actually worked exactly as described - I uploaded a complete mess of tax documents (some I had to dig out of old email accounts) and it organized everything perfectly by year. The document analysis saved me hours of manually sorting through paperwork and double-checking numbers. I was able to identify all my income sources for each year and make sure I wasn't missing anything important. I ended up finding a 1099-MISC from a small freelance job in 2021 that I had completely forgotten about! I used the organized information with FreeTaxUSA as suggested earlier in this thread, and I've already mailed in both my 2021 and 2022 returns. Now just waiting for those refunds!

If you're concerned about any issues with your back taxes or need to contact the IRS with questions, I highly recommend using https://claimyr.com to get through to an IRS agent quickly. I waited on hold for 3+ hours trying to ask questions about my unfiled returns before giving up. Then I tried Claimyr and got through to someone in about 15 minutes! They basically hold your place in the IRS phone queue and call you when an agent is available. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c I had questions about some specific forms I needed to include with my prior year returns, and being able to actually talk to an IRS representative made all the difference. They clarified exactly what I needed to do and saved me from making mistakes that would have delayed my refunds.

I need to publicly eat my words here. After expressing skepticism about Claimyr in my previous comment, I decided to try it myself since I had some questions about amending one of my past returns. I was absolutely shocked when I got a call back in about 20 minutes saying they had an IRS agent on the line. The connection was seamless - one minute I was talking to the Claimyr rep, the next I was speaking with an actual IRS employee who answered all my questions about the amendment process for my 2020 return. I've literally never been able to get through to the IRS in less than an hour before, and sometimes I've given up after 2+ hours on hold. This honestly saved me so much frustration and I got the exact information I needed. Just wanted to share since I was so openly doubtful before.

One thing to consider - if you're filing back taxes and expect refunds, double check if you had any stimulus payments during those years. For 2021 especially, if you didn't receive the third stimulus payment ($1,400 per person), you might be eligible to claim the Recovery Rebate Credit on your return. Also, if you had children and were eligible for the expanded Child Tax Credit in 2021, make sure that's accounted for. Those were partially sent as advance payments, but you might be eligible for the remainder. Those two things alone could significantly increase your refund for 2021!

I just went through this whole process of filing 3 years of back taxes. My biggest piece of advice is to gather ALL your documents before starting. Make a checklist: - W-2s from all employers for each year - 1099s (interest, dividends, contractor work, etc) - Mortgage interest statements - Student loan interest - Health insurance forms - Any major life events (buying home, education, etc) Once you have everything organized by year, the software is actually pretty straightforward. I used TaxSlayer for all my back years and while it was a bit pricey (about $40 per year including state), their interface was really easy to use for someone who was overwhelmed like I was.