Can I use FreeTaxUSA to file multiple years of back taxes efficiently?

You're definitely not alone in this situation! I help people with catch-up filing pretty regularly. Here's what I recommend: File your 2023 taxes first since the deadline for those is still coming up (April 15, 2025). This ensures you don't add another year to your backlog. After that, work backwards from newest to oldest (2022, then 2021, then 2020). FreeTaxUSA is actually a good choice for back taxes because they only charge $14.99 for prior year federal returns (state returns are extra though). The interface stays pretty consistent across tax years which makes it easier when doing multiple years back-to-back. One important thing to know: you can only e-file the current year (2023). For 2020-2022, you'll need to print and mail the completed returns. Make sure you send each year in separate envelopes with the appropriate documentation for each.

I was in almost the exact same situation last year - hadn't filed for 3 years and was freaking out. I ended up trying https://taxr.ai after seeing it mentioned on reddit, and it was seriously a lifesaver for catching up on my back taxes. You upload all your tax documents (W-2s, 1099s, etc.) from those years, and it pulls all the information automatically then helps you file everything correctly. The best part was that it organized everything by year and walked me through each return step by step. It was way easier than trying to navigate different tax years manually in FreeTaxUSA (which I had initially tried and got confused with). Might be worth looking into if you have a lot of different tax forms across those years.

Just wanted to follow up and say I gave https://taxr.ai a try for my backed up returns and I'm genuinely impressed. I was skeptical at first (as you can see in my earlier comment), but it handled my rental property and side business stuff without any issues. The document scanning feature was surprisingly accurate - it pulled all the numbers correctly from my messy pile of tax forms. Finished filing 3 years of returns in one weekend instead of the weeks I was expecting it to take. Definitely recommend for anyone in a similar situation with multiple years to catch up on!

If you're trying to contact the IRS about your back taxes situation, good luck getting through on their phone lines. I spent literally 8+ hours on hold across multiple days trying to ask questions about my unfiled returns. Finally found https://claimyr.com and watched their demo video at https://youtu.be/_kiP6q8DX5c - they actually have a system that holds your place in the IRS phone queue and calls you when an agent is about to answer. I was pretty doubtful it would work, but I got a call back with an actual IRS agent within about 2 hours. The agent helped me understand exactly what I needed to do with my unfiled returns and even set up a payment plan for what I owed. Saved me days of frustration trying to get through on my own.

I have to eat my words and admit I was wrong. After posting my skeptical comment, I decided to try Claimyr anyway out of desperation. I had 4 years of unfiled taxes and needed specific guidance that I couldn't get from the IRS website. Got a call back in about 90 minutes with an actual IRS representative on the line. The rep was able to tell me exactly which forms I needed for my specific situation and confirmed I wasn't facing any penalties yet if I filed quickly. I've been stressing about this for months and finally have a clear plan forward. Honestly wish I'd known about this service sooner instead of repeatedly banging my head against the wall trying to get through myself.

Quick tip from someone who's gone through this: Make sure you have all your documents organized by year before you start. Gather all W-2s, 1099s, mortgage statements, etc. for each tax year and keep them separate. Makes the process so much easier. Also, FreeTaxUSA will let you download PDFs of your completed returns, but keep physical copies too just in case. The IRS can ask for documentation for up to 7 years, so better safe than sorry.

Anyone know if there's a penalty for filing late if you're actually owed a refund? I think I'm probably due money back for at least two of the years I didn't file.

Jessica, I totally feel your stress about this! I was in a similar boat a few years ago and it's really not as scary as it seems once you get started. One thing I'd add to the great advice already given - make sure you check if you're owed any refunds for those years, especially 2020. Like others mentioned, you only have 3 years to claim refunds, so the 2020 refund deadline is approaching fast (April 15, 2024 was the original deadline, so you'd have until April 15, 2027 to claim it, but double-check this with the IRS). Also, don't beat yourself up about this. Life happens, and the IRS deals with catch-up filers all the time. The important thing is you're taking action now. Once you get through the first return, the others will feel much more manageable. You've got this! If you do end up owing money, the IRS is usually pretty reasonable about setting up payment plans too. The key is just getting everything filed so you know where you stand.

Jessica, you're definitely making the right move by tackling this now! I was in your exact shoes about three years ago - hadn't filed from 2017-2019 and was completely overwhelmed. Here's what worked for me: I started with the most recent year first (like Angelina suggested) and worked backwards. This strategy helped because the forms and tax laws were fresher in my memory for recent years, and it built my confidence before dealing with older returns. One thing I wish someone had told me - keep detailed records of everything as you go. Create a simple spreadsheet tracking which years you've completed, what you owe/are owed, and confirmation numbers for any payments or filings. This saved me so much headache later when I needed to reference things. FreeTaxUSA is solid for this situation. The interface is user-friendly and their customer support actually helped me when I got stuck on some tricky deduction questions for my 2018 return. Just remember that you'll be mailing the older years, so budget extra time for printing, organizing, and trips to the post office. The hardest part is just starting - once you complete that first return, you'll feel so much relief and momentum to knock out the rest. You've got this!