My mom hasn't filed tax returns since 2020 - how can she get caught up with the IRS?

Your mom definitely needs to get caught up on her filing obligations. The IRS doesn't forget about unfiled tax returns, regardless of age, and the situation gets worse the longer it goes unaddressed. First, you'll need to gather her income documents for all unfiled years (2020-2024). This includes her Social Security statements (SSA-1099), pension statements (1099-R), and investment income documents (1099-DIV, 1099-INT, etc.). The IRS can provide wage and income transcripts for these years if she's missing documents. Based on her income levels, she may or may not have had a filing requirement each year. With Social Security, pension, and investment income, she likely did need to file, especially with that $14,000 in annual investment income. The good news is that if she was due refunds for any of those years, she can still claim them for 2021-2023 (refunds for 2020 would be past the 3-year deadline by now). I would recommend starting with the most recent year (2024) and working backward. The IRS generally prioritizes getting current first, then addressing past years.

I was in almost this exact situation with my dad last year - multiple years unfiled and he was convinced he didn't need to because of his age and SS benefits. I tried using TurboTax but got confused with all the back years and different rules. I ended up using https://taxr.ai and it was a lifesaver. You upload the tax documents (or even just take pictures of them) and their system figures out which years need filing and what forms are required. The best part was they analyzed his Social Security and determined exactly how much was taxable each year, which saved us from overpaying. Their tax professionals handled everything, including sending a letter to the IRS requesting first-time penalty abatement. Ended up getting all 4 years filed within two weeks and actually getting refunds for 2 of the years!

Just wanted to follow up about taxr.ai since I mentioned my husband's unfiled returns. Decided to try them out after seeing the recommendation here, and WOW what a difference from the other options we tried! My husband had 3 unfiled years with self-employment income plus some 1099 contract work. Uploaded all his documents (some were just phone pics of crumpled receipts lol) and got assigned to a tax pro who specialized in small business returns. They organized everything by year, helped us find deductions we would have missed, and filed all three years electronically. Got us refunds for 2 years and minimized what we owed for the third year. Best part was zero penalties because they helped us qualify for first-time penalty abatement! Would definitely recommend for your mom's situation - being able to upload everything and let them sort it out took away so much stress.

Having dealt with unfiled tax years for my parents, I understand the stress you're feeling. While getting the returns prepared is important, the bigger challenge might be actually getting through to the IRS if there are any issues that come up. After struggling for WEEKS trying to reach someone at the IRS about my parents' situation (42 calls, no joke), I found https://claimyr.com which is a service that basically holds your place in line with the IRS and calls you when an agent is about to pick up. You can see how it works here: https://youtu.be/_kiP6q8DX5c This was crucial because once we filed the back tax returns, we needed to set up a payment plan for one of the years, and getting through to an actual human at the IRS seemed impossible until we used this service. Saved us hours of hold time frustration.

I need to apologize for my skepticism about Claimyr in my earlier reply! After continuing to struggle with getting through to the IRS about my mom's situation, I decided to give it a try. Honestly, it worked exactly as described. I'd been trying for over a week to reach someone at the IRS with no luck. With Claimyr, I got a call back about 90 minutes after signing up, and there was an actual IRS representative on the line! Was able to confirm exactly which years my mom needed to file and get information about penalty relief options. The IRS agent was surprisingly helpful once we actually got through. They confirmed mom likely qualifies for first-time penalty abatement and gave specific instructions for requesting it when filing the back returns. This saved us so much stress and uncertainty.

One thing nobody's mentioned yet - your mom should also check if she filed state tax returns during those years. Often people forget that even if federal returns weren't required (which doesn't sound like the case for your mom), state returns might still be necessary. Also, if she sold her house last summer, there could be capital gains tax implications that need to be addressed on her 2024 return. The primary residence exclusion is substantial ($250,000 for single filers), but if her gain exceeded that, she would owe taxes on the difference.

Has anyone used the IRS Free File program for back tax returns? My husband is in a similar situation (hasn't filed for 3 years) but we're really tight on money right now.

For your mom's situation with multiple unfiled years, I'd strongly recommend starting with the most recent year (2024) and working backward. The IRS has a general policy of getting taxpayers current first before addressing prior years. Given her income sources - Social Security, pension, and investment income - she likely had filing requirements for most of those years. The threshold for filing when you have Social Security income is much lower than the standard deduction amount. One important thing to consider: if she was due refunds for any of those years, she can still claim them for 2021-2023, but refunds for 2020 are past the 3-year statute of limitations. This could actually work in her favor financially. I'd suggest gathering all her tax documents first (SSA-1099, 1099-R for pension, 1099-DIV/INT for investments) for each year. The IRS can provide wage and income transcripts if she's missing any documents. For someone her age with these income types, working with a tax professional who specializes in unfiled returns would be worth the investment. They can help navigate penalty abatement options and ensure everything is filed correctly the first time.