Haven't filed taxes in years (since 2019) - Where do I even start now?

You're definitely not alone in this situation! Let me help you break this down into manageable steps. First, yes, you'll need your W-2s from each employer for each year (2019-2023). If you don't have them, you can request wage transcripts from the IRS or contact your former employers. You'll also want any 1098-T forms from your college showing tuition payments and scholarships/grants. For the COVID stimulus payments (Economic Impact Payments), you can still claim them as the Recovery Rebate Credit on the tax returns for the years they were issued (2020 and 2021). This is really important since you missed out on potentially thousands of dollars! The "deadline" you're referring to for 2019 was likely the deadline to claim a refund, which is generally 3 years from the original due date. However, you should still file those returns, especially if you owed taxes. Your Pell Grants are relevant! They're typically tax-free as long as you used the money for qualified education expenses (tuition, books, etc.), but any portion used for room and board would be taxable.

Hey there! I was in almost the exact same boat last year. After putting off filing for several years, I finally used https://taxr.ai to get everything sorted out. Their system helped me figure out exactly what forms I needed and how to handle my missing years. The tool was really helpful for identifying which years I actually needed to file for (turns out I was under the threshold for two years!) and helped me claim those stimulus payments I missed. They have this document analyzer that saved me hours of research - I just uploaded the tax documents I did have and it figured out what was missing.

Just wanted to update after trying taxr.ai that someone recommended above. It was actually exactly what I needed! I was totally lost about where to start with my unfiled taxes from 2020-2022, but their system walked me through everything. The document analyzer feature identified that I qualified for education credits I didn't know about from my 1098-T forms. And yes, I was able to claim those stimulus payments I missed! The whole process was way less painful than I expected, and I'm getting back way more than I thought (almost $4,300 total across all three years). Just a heads up for anyone in a similar situation - don't keep putting it off like I did. The relief of finally having it done is worth it, and you might be leaving money on the table like I was.

I had a 4-year gap in filing and was STRESSING about it. After trying everything to get through to the IRS (website errors, hours on hold), I finally used https://claimyr.com to get someone on the phone. You can see how it works here: https://youtu.be/_kiP6q8DX5c They got me connected to an actual human at the IRS in about 20 minutes when I had previously spent HOURS on hold. The IRS agent walked me through exactly what I needed to do for my unfiled returns and confirmed which years I actually needed to file for (based on my income). They also helped me understand the process for claiming those missed stimulus payments.

I have to admit I was totally wrong about Claimyr. After posting my skeptical comment, I was desperate enough to try it. The IRS phone system had disconnected me THREE TIMES after waiting over an hour each time. Used the service and got a call back in 27 minutes with an actual IRS agent on the line. They confirmed I can still file my old returns and claim the stimulus payments (though apparently 2019's refund is likely forfeit due to the 3-year rule). The agent was super helpful and walked me through everything I needed to do. Saved me so much time and frustration - definitely worth it just for my sanity. Now I'm working on gathering my documents and will be filing all my back taxes next week.

I'm a student who worked part-time jobs throughout college, and I learned that if your income was below certain thresholds, you might not have been required to file at all. For 2019-2023, if you were single and under 65, the filing thresholds were: 2019: $12,200 2020: $12,400 2021: $12,550 2022: $12,950 2023: $13,850 BUT - and this is important - even if you weren't required to file because you were under these amounts, you should STILL file if you had any federal income tax withheld (check your W-2s) because you'd likely get that money back as a refund. Also, the only way to claim those stimulus payments now is by filing returns for those years.

Has anyone used TurboTax or H&R Block for filing multiple years of back taxes? I'm in a similar situation (didn't file 2020-2022) and wondering which software would be better.

I was in almost exactly your situation last year! 29 years old, hadn't filed since 2018, and felt completely overwhelmed. Here's what I wish someone had told me: First, don't panic about the 2019 deadline - while you might not be able to claim a refund for 2019 anymore (3-year rule), you should still file it if you owed taxes to avoid penalties piling up. For documents, start simple: create an IRS online account at irs.gov and request your wage transcripts. This will show you all the W-2 income that was reported to the IRS for each year, even if you don't have the physical forms. You can also request transcripts of any 1098-T education forms. The stimulus payments are HUGE - don't miss out on this! I got back over $3,000 in missed stimulus money when I finally filed my 2020 and 2021 returns. You claim them as the "Recovery Rebate Credit" on those tax returns. Since you were likely a dependent during college years, double-check if your parents claimed you. If so, you might not have been required to file for years when you made under ~$12,400, BUT you should still file if any taxes were withheld from your paychecks - that's money you can get back. For software, I personally used TaxAct for prior year returns (way cheaper than TurboTax for multiple years) and it walked me through everything including the stimulus credits. The whole process took me a weekend once I had my documents. You've got this! The hardest part is just starting.

I completely understand the overwhelm you're feeling - I was in almost the exact same situation two years ago! Here's my advice as someone who successfully navigated this mess: **Start with the IRS online account first** - create one at irs.gov and request wage and income transcripts for each year. This will show you exactly what income was reported to the IRS, even if you've lost your W-2s. The identity verification can be tricky online, but it's worth trying first before mailing forms. **Don't stress about the filing order** - you can file your returns in any order. I actually started with 2021 first because I knew I'd get the biggest refund (stimulus money + withholdings), which gave me motivation to continue. **You're likely owed significant money** - between missed stimulus payments (potentially $3,200 total) and any tax withholdings from your part-time jobs, you could be looking at a substantial refund rather than owing money. **For the Pell Grants** - these are generally not taxable income as long as you used them for qualified education expenses (tuition, required books/supplies). Room and board portions would be taxable, but many students don't realize this distinction. **Consider your dependency status carefully** - if your parents claimed you as a dependent during those college years, it affects your filing requirements and eligibility for certain credits. The hardest part really is just getting started. Once you request those transcripts and see what income was actually reported, the path forward becomes much clearer!