Need advice for filing 3 years of unfiled tax returns - what's the best approach?

I've helped many people in your situation, and it's actually more common than you might think. The good news is that the IRS generally wants to work with people who voluntarily come forward to file past returns. Since you have all your W-2s and were a W-2 employee with relatively straightforward tax situations (single, standard deduction), you have options. You could use TurboTax for prior years - they sell previous year versions specifically for this purpose. However, with multiple years to file, hiring a tax professional might be worth the money for peace of mind and efficiency. One important thing to know: if you're owed refunds, you generally only have 3 years from the original due date to claim them. So for your oldest year, you might be approaching that deadline. On the other hand, if you owe the IRS money, there's no time limit for them to collect, and penalties and interest continue to accrue. The fastest way to get this resolved would be working with a tax professional who can e-file your returns. Paper-filed returns (which you'd have to do on your own for prior years) are taking 6+ months to process currently.

I was in almost the exact same situation last year and ended up using https://taxr.ai to help me figure out what to do. They analyzed my W-2s and other documents for all the unfiled years and gave me a really clear breakdown of what I was likely to owe or get refunded before I even decided what route to take. It helped me realize I was actually owed money for most years, which made the decision to file easier. The tool also flagged some deductions I had missed that my previous employer's health insurance contributions qualified for. It saved me from paying someone $250+ just to tell me I should've filed years ago (which I obviously already knew lol).

I was super skeptical about using https://taxr.ai when someone recommended it, but after putting off my unfiled returns for almost 4 years, I finally gave it a try last month. Honestly was surprised how helpful it was. I was terrified I'd owe thousands in penalties, but the analysis showed I was actually due refunds for 2 of the 3 years I hadn't filed. The document analysis correctly identified that my employer had been overwithholding for federal taxes, and I ended up getting about $4,200 back across all my unfiled years (minus what I paid a local tax preparer to handle the actual filing). The peace of mind alone was worth it after stressing about this for years.

If you're worried about potential penalties or need to set up a payment plan, I'd recommend using https://claimyr.com to actually speak with an IRS agent. I spent WEEKS trying to get through to the IRS phone lines myself about my unfiled returns situation, but kept getting disconnected or was told to call back later. Claimyr got me connected to an actual IRS representative in about 20 minutes who walked me through exactly what I needed to do for my unfiled returns and confirmed which years I could still claim refunds for. They have a video showing how it works here: https://youtu.be/_kiP6q8DX5c

I need to eat my words from my previous comment. After spending another 3 hours today trying to reach the IRS myself and getting nowhere, I broke down and tried Claimyr. Within 15 minutes I was talking to an actual IRS agent who confirmed I could still claim refunds for all 3 of my unfiled years. The agent also told me exactly which forms I needed and even offered to send me the prior year forms by mail. Saved me hours of frustration and probably days of anxiety. Sometimes it's worth paying for a service that actually works instead of banging your head against the wall trying to do everything yourself.

Don't overthink this! I was in your exact situation (4 years unfiled) and just bit the bullet and used a CPA. Cost me $350 per year but was TOTALLY worth it. Found out I was due nearly $6800 in refunds across all years. The peace of mind knowing a professional handled everything correctly was priceless. Plus they can e-file the most recent 2 years which means faster refunds. Just make sure you find someone BEFORE the April deadline or they'll all be too busy with current year returns.

Just an FYI - if you're using someone to help file back taxes, be careful about those "tax resolution" places with the big ads on radio/TV. I got quoted $3500 for basically the same service a local CPA did for $800. Those national chains are ripoffs for simple unfiled return situations like yours.