What's the best way to catch up on unfiled tax returns from 2013-2017?

Getting caught up on prior year returns is definitely doable! I help people with this situation pretty regularly. First, you should know that e-filing is unfortunately not available for prior year returns - you'll need to mail in paper forms. But the good news is you can still use tax software to prepare them, then print and mail. For years 2019 and forward, you can still e-file. For 2013-2017, you'll need the forms specific to those tax years. Don't use current year forms for prior years as tax laws change. Since you mentioned having modest income, you might qualify for free tax preparation through VITA (Volunteer Income Tax Assistance) programs, though they typically focus on current year returns. For DIY options, FreeTaxUSA allows you to prepare prior year returns for a reasonable fee (much cheaper than TurboTax or H&R Block). You can also download the specific year forms directly from the IRS website and fill them out manually. I would recommend tackling the most recent unfiled years first, as those are more likely to have refunds you can still claim (the deadline for claiming refunds is generally 3 years from the original due date).

I was in almost the exact same situation last year, had to catch up on 4 years of back taxes. I was freaking out until I found this service called taxr.ai (https://taxr.ai) that made the process so much easier than I expected. What I liked is they have this tool that can scan all your tax documents at once and organize everything by tax year, which saved me hours of sorting through old W-2s and 1099s. The system automatically pulled the relevant info for each tax year and filled out the forms. For prior year returns, they generated all the correct forms with the right tax laws for each specific year, which is apparently super important because tax laws change almost yearly. I still had to mail in the physical forms for the older years, but everything was prepared correctly.

Just wanted to update. I tried taxr.ai after asking about it here, and it actually worked really well for me! I was able to process all 5 years of my back taxes in one weekend instead of the weeks I thought it would take. Their document scanner saved me from manually entering data from 14 different W-2s across all those years. The interface showed me potential deductions I didn't know about for each specific tax year. When it came time to file, they generated all the correct year-specific forms and gave clear instructions for mailing them in. Already received confirmation from the IRS that they processed my 2016 and 2017 returns!

If you're trying to contact the IRS to sort out any issues with your back taxes, good luck getting through on their phone lines. I spent DAYS trying before I found Claimyr (https://claimyr.com). They somehow get you through the IRS phone maze and have an agent call you back. Saved me literally hours of hold time. You can see how it works here: https://youtu.be/_kiP6q8DX5c After filing my back taxes, I had questions about some penalties that showed up. Used their service and had an actual IRS person call me within about 30 minutes. The agent was able to explain the penalty situation and even removed one of them since I had legitimate reasons for the late filing.

I need to publicly eat my words from my skeptical comment above. After continuing to fail getting through to the IRS on my own for another week, I broke down and tried Claimyr. It actually worked! Got a call back with an IRS representative in about 45 minutes. I was able to get confirmation that my 2015-2017 returns were processed and set up a payment plan for the taxes I owed plus penalties (which were less than I feared). The agent also gave me info about penalty abatement I might qualify for since my late filing was partly due to documented medical issues. Definitely worth it for the time saved and stress reduction alone.

One small tip I learned the hard way - keep copies of EVERYTHING you send to the IRS when filing back taxes. I mean everything - the returns themselves, W-2s, 1099s, any supporting documents, and proof of mailing (certified mail with return receipt). I had an issue where the IRS claimed they never received my 2016 return that I sent in, and because I had good records, I was able to prove I had submitted it.

Has anyone used TurboTax to file prior year returns? Their software lets you buy previous years but I'm not sure if it's worth the cost.

Don't forget about state taxes too! I caught up on my federal returns and completely forgot I needed to do state returns as well. Had to go back and do the whole process again. Most states have similar rules for prior year returns (paper filing only).

Great advice in this thread! One thing I'd add that helped me when I caught up on my back taxes - consider filing in chronological order (oldest first) rather than all at once. This can help avoid potential processing delays or confusion at the IRS, especially if there are carryover items like net operating losses or credits that might affect multiple years. Also, if you discover you made errors on returns you've already filed while working on the older ones, you can file amended returns (Form 1040X) to correct them. Just keep in mind the 3-year deadline for claiming additional refunds applies to amended returns too. The IRS actually has a pretty helpful "Get Transcript" tool on their website where you can see what they have on file for you for each year. It's worth checking before you start to see if they've already processed substitute returns for any years (they sometimes do this when people don't file). If they have, you'll want to file your actual returns to replace their estimates, which are usually not in your favor.