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

Hey everyone, I'm in a bit of a jam here. I've been really bad about my taxes and haven't filed anything from 2020 through now. Life got complicated, and I just kept putting it off until it snowballed into this mess. I used to have an accountant who handled everything when I was finishing college out of state, but now I'm trying to save some cash and wondering if I can just handle this myself online. I've heard decent things about FreeTaxUSA and think it might work for my situation. My question is about the strategy - should I start with filing my most recent 2023 taxes first and then work my way backwards to 2020? Or is it better to start with the oldest (2020) and move forward chronologically? This is all new territory for me and I'm honestly feeling pretty overwhelmed about tackling 4 years worth of tax returns. Any advice from people who've been in similar situations would be super helpful!

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19 comments

Angelina Farar

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.

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Angelina Farar

The IRS doesn't technically care about the order you file past-due returns, but there are practical reasons to file newest first. Filing 2023 first ensures you don't miss another deadline, and if you're owed refunds, the most recent years are less likely to have expired refund windows. For 2020 specifically, the refund statute of limitations is likely closing soon (generally 3 years from the original due date), so if you're owed money for that year, you might be running out of time to claim it. However, if you owe money, there's no time limit for the IRS to collect, which is another reason to get everything filed asap.

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Bethany Groves

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.

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Bethany Groves

They do handle state returns alongside federal, including California. The system automatically creates the state return once your federal is complete, which saved me tons of time. For business expenses and rental income, it actually works great for those situations too. I had some 1099 work and the system categorized all my business expenses properly. It has specific sections for rental income where you can input property details, rent collected, and related expenses. It's actually more thorough than I expected for complex tax situations.

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Rebecca Johnston

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!

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Nathan Dell

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.

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Nathan Dell

It doesn't auto-dial repeatedly - they use a legitimate system that navigates the IRS phone tree and essentially waits in the queue for you. It's completely legitimate and doesn't violate any rules - they're just holding your place in line. The reason it works is they've figured out exactly which prompts to select and when to call to maximize your chances of getting through. Once they reach a certain point in the queue, their system calls you and connects you with the IRS agent. I was skeptical too before trying it, but it's basically just outsourcing the hold time so you don't have to sit there listening to the hold music for hours.

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Tristan Carpenter

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.

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Amaya Watson

FreeTaxUSA does allow some information to carry forward, but it works best when done in chronological order. If you do 2020 first, then 2021, basic info like your personal details, dependents, etc. will transfer. However, since you'd be doing these all at once rather than in different tax seasons, the process is a bit different. Each tax year is technically a separate product in their system, so you'll need to create returns individually for each year. But you can use the "prior year" option to help with some of the basic information transfer. Just be careful to verify all the imported info since tax situations can change year to year.

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Freya Nielsen

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.

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