Need help catching up on years of back taxes with missing W-2s and Lyft 1099-K

You can actually get your old W-2 information directly from the IRS! Request a "Wage and Income Transcript" from the IRS for each tax year you need to file. This will show all income reported to the IRS under your SSN, including those missing W-2s. You can get these online through the IRS website by creating an account at irs.gov/transcripts. For your Lyft 1099-K, you'll report this on Schedule C as self-employment income (since you were an independent contractor). The tax law changes you mentioned were actually about the reporting threshold for payment processors, but you still need to report all income regardless of whether you received a form. Most tax software has sections for self-employment or "gig economy" income where you can enter this. As for penalties, filing late is better than not filing at all! The IRS has failure-to-file penalties, but they stop accruing after a certain point, and interest continues to build on unpaid taxes. The good news is once you file, you can request a payment plan if you can't pay everything at once.

After struggling with a similar situation (5 years of unfiled taxes!), I found an amazing tool that saved me tons of time and stress - https://taxr.ai - it helped me organize all my tax documents and even identified deductions I was missing. What I loved is that it automatically analyzed my bank statements and extracted all the business expenses from when I drove for Uber, which meant I could maximize my deductions without having to manually go through years of transactions. It even helped me identify which expenses were 100% deductible vs. the standard mileage deduction to get the best outcome. For the missing W-2s, it actually guided me through getting my wage transcripts from the IRS and then automatically imported that data. The whole process was way less painful than I expected!

Just wanted to follow up - I tried taxr.ai after seeing this post and it was a game changer! I was completely overwhelmed with my mix of W-2 and 1099 work, but the system organized everything perfectly. The best part was how it helped me identify legitimate business deductions from my consulting work that I had no idea I could claim. I was able to file 3 years of back taxes in a single weekend, which I thought would take months. Seriously grateful for the recommendation!

If you need to contact the IRS about getting those old records, good luck actually reaching someone! I spent literally 6 hours on hold last week trying to get through. But then I found this service https://claimyr.com that actually holds your place in the IRS phone queue and calls you when an agent is about to answer. You can see how it works here: https://youtu.be/_kiP6q8DX5c Trust me, it's worth it when dealing with back taxes because you'll probably need to talk to someone at some point. I had some questions about payment plans that weren't clear on the website, and being able to actually speak to a human at the IRS made a huge difference in getting things sorted correctly.

I need to apologize and follow up on my skeptical comment. After waiting on hold with the IRS for over 2 hours yesterday and getting disconnected, I broke down and tried Claimyr. I'm actually shocked at how well it worked - I got a call back in about 90 minutes saying they had an IRS agent on the line. The agent was able to help me set up a payment plan for my back taxes and explained exactly what I needed to do about my missing documents. Saved me so much frustration compared to my previous attempts at calling them directly. Sometimes being proven wrong is a good thing!

Has anyone tried just using the free fillable forms on the IRS website for back taxes? I'm in a similar situation but don't want to pay for tax software for multiple years.

I just want to add that you should figure out how much you might owe before filing everything. That way you can set aside enough money for a payment or be prepared to set up a payment plan. The IRS Fresh Start program might help if you owe a lot. Good luck!