Haven't filed taxes since 2019 - where do I start? Need guidance for multiple years

You definitely need to get caught up on filing, but don't panic! The good news is that if you're owed refunds, there's no penalty for filing late. However, you typically only have 3 years from the original filing deadline to claim a refund, so 2019's refund window just closed recently (April 2023 was the cutoff). For each year, you'll need: - W-2s from all employers - 1098-T forms from your college (shows tuition paid and scholarships/grants received) - Any 1099 forms if you had side gigs or investment income - Records of major education or medical expenses Regarding the stimulus payments (Economic Impact Payments), you can still claim the 2020 and 2021 payments as Recovery Rebate Credits on those tax year returns if you qualify. They won't be on your 2019 return. Since you mentioned Pell Grants, those are generally tax-free as long as you used the money for qualified education expenses like tuition and fees. However, if you used any portion for living expenses, that part would be taxable. I'd recommend starting with your most recent unfiled year (2022) and working backward. Filing electronically will be much faster than paper returns.

I was in a similar situation last year - hadn't filed for 3 years and was stressing big time! I tried using TurboTax but kept getting confused with all my missing documents. Then a friend recommended this AI tax assistant at https://taxr.ai and it was a COMPLETE game changer for me. The system analyzed my situation and walked me through exactly what forms I needed for each year. It even helped me figure out which years I actually needed to file for based on my income levels, and which stimulus payments I could still claim. The best part was that it found some education credits I didn't know about from my college expenses. For someone in your situation with Pell Grants and everything, I bet you'd find some benefits too. They have special tools for catching up on multiple years of unfiled taxes.

Update: Just wanted to share that I took the advice about https://taxr.ai and it was seriously helpful! I was missing W-2s from 2020 and 2021, and the system walked me through getting my wage transcripts from the IRS which had everything I needed. The biggest surprise was finding out I qualified for the American Opportunity Tax Credit for the years I was in school, which I had no idea about. Between that and the Recovery Rebate Credits for the stimulus payments I never got, I'm actually getting back over $5,000 across all my returns! The system also told me exactly which years I actually needed to file based on my income levels. Turns out I didn't even need to file for 2020 because I was under the threshold, but filing anyway let me claim the stimulus money.

If you're struggling to get through to the IRS to get old documents or resolve any issues, I'd recommend trying https://claimyr.com - completely saved me when I was in a similar situation. You can see how it works here: https://youtu.be/_kiP6q8DX5c I had to contact the IRS about missing stimulus payments from years ago and kept getting the "call back later" message for WEEKS. Claimyr got me connected to an actual IRS agent in about 15 minutes. They basically hold your place in line so you don't have to keep redialing hundreds of times. When I finally got through, the agent helped me request all my missing documents and gave me specific guidance on filing my late returns. They were surprisingly helpful once I actually got to speak to someone!

I have to admit I was completely wrong about Claimyr. After commenting here, I decided to try it as a last resort since I was desperate to talk to someone at the IRS about my unfiled returns from 2020 and 2021. It actually worked exactly as described. I got connected to an IRS representative in about 20 minutes after weeks of trying on my own with no success. The agent helped me figure out exactly what forms I needed to file for my missed years and confirmed which stimulus payments I could still claim. They also told me that while the 2019 refund window has closed, I should still file the return if I owed taxes to avoid additional penalties and interest. For someone trying to catch up on multiple years like the original poster, being able to actually speak with an IRS agent makes a huge difference.

Don't forget about state taxes too! Everyone's talking about federal returns but you probably need to file state returns for those years as well. Each state has different thresholds for who needs to file.

FYI - definitely get your Pell Grant info in order. If you used the money for anything besides tuition, fees, books, and required supplies, you might owe taxes on that portion. Like if you used some for rent or food.