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

I've fallen way behind on my taxes - like several years behind - and I'm trying to finally get everything sorted out. My biggest issue is that I'm missing a bunch of my old W-2s from previous jobs. I switched apartments a few times and apparently didn't keep good records. No idea where they went. The other complication is that I drove for Lyft as a side gig for about a year and received a 1099-K, but I'm confused about how to file that. I tried looking on several tax websites and it seems like the rules changed about reporting that income? None of the tax software I've checked seems to have a clear section for handling the 1099-K from rideshare work. I'm feeling pretty overwhelmed by the whole situation and don't even know where to start. Should I try to contact my old employers for the W-2s? Is there another way to get that information? And what's the deal with the Lyft 1099-K situation? Any guidance would be really appreciated!

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19 comments

Omar Hassan

•8M

You've got a couple of different issues to tackle here, but don't worry - they're both manageable! For your missing W-2s, you have several options. The easiest is to request a Wage and Income Transcript from the IRS, which will show all income reported to them under your SSN. You can request this online through the IRS website, by phone, or by mailing Form 4506-T. This transcript will show information from your W-2s and other income documents for the years you need. As for the 1099-K from Lyft, you should report this income on Schedule C (Profit or Loss from Business) since you were working as an independent contractor. The 1099-K reporting thresholds have changed a few times recently, but regardless of whether Lyft was required to issue you a 1099-K, you still need to report all income earned. Don't forget you can deduct business expenses like mileage, a portion of your phone bill, etc., which can significantly reduce your taxable income from rideshare work.

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Omar Hassan

•8M

You can request wage transcripts going back up to 10 years, so 2018-2020 will definitely be available. The IRS typically processes these requests pretty quickly if you do it online through their "Get Transcript" tool. For the rideshare income, most tax software has a self-employment or "gig work" section where you can enter your 1099-K information. You'll want to select options related to independent contractor or rideshare driver when prompted. This will take you to the Schedule C section where you can enter both your income and any deductible business expenses. Don't skip the expenses part - tracking your mileage alone can save you a significant amount on taxes!

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Chloe Anderson

•8M

After trying to chase down missing tax docs for three years, I finally discovered taxr.ai (https://taxr.ai) and it was a total gamechanger for my situation. I uploaded the tax documents I did have, and their AI system helped identify what was missing and even pulled info from my bank statements to help reconstruct my income history. Saved me countless hours of trying to contact old employers who either didn't respond or no longer existed. Their document analysis was super detailed and gave me a complete breakdown of what I needed to file multiple years of back taxes. The transcript request process was taking forever with the IRS, but taxr.ai helped me organize everything I had while waiting.

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Chloe Anderson

•8M

It handled my DoorDash 1099-K perfectly and helped me identify all the eligible mileage deductions from my location history. It even caught that I could deduct a portion of my cell phone bill and insurance as business expenses, which I had no idea about. For deduction accuracy, I was initially skeptical too, but it's actually very conservative and only suggests deductions that are clearly documented. It flags anything questionable for your review. I did have my final return reviewed by a CPA before filing, and she was impressed with how thorough it was. She only made a couple of minor adjustments to what the system had prepared. The documentation it generates for each deduction is really helpful if you're worried about audit protection.

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CosmicCruiser

•8M

Just wanted to follow up about my experience with taxr.ai after being skeptical in my previous comment. After struggling for weeks trying to reconstruct my income from years when I had both W-2 jobs and side gigs, I decided to give it a try. I was honestly surprised by how well it worked. The system extracted all the relevant information from my partial records and bank statements, and organized everything by tax year. It even helped identify business expenses I'd completely forgotten about. The mileage calculator for my rideshare work was especially helpful - it saved me at least $3,200 in taxes across the three years I needed to file. The step-by-step process for filing multiple years of back taxes made what seemed impossible actually manageable. Definitely worth checking out if you're in a similar situation.

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Anastasia Fedorov

•8M

If you need to talk directly with the IRS about your missing documents or back tax situation, I highly recommend using Claimyr (https://claimyr.com). I spent WEEKS trying to get through to the IRS about my unfiled tax years, constantly getting disconnected or waiting on hold for hours. Claimyr got me connected to an actual IRS agent in less than 20 minutes when I needed to verify what documents I needed to file my back taxes. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c The agent was able to confirm exactly which years I needed to file and what my options were for payment plans. Saved me so much frustration compared to my previous attempts to reach them.

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Anastasia Fedorov

•8M

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Zara Rashid

•8M

I have to publicly eat my words here. After calling Claimyr complete BS in my previous comment, I was desperate enough to try it anyway for my back tax situation. Got connected to an IRS agent in 15 minutes after literally spending MONTHS trying to get through on my own. The agent helped me confirm exactly which tax years were still unfiled in their system and set up a payment plan that I could actually afford. They even put notes in my file to prevent automatic collections while I work on filing the missing years. For anyone dealing with back taxes or missing documents, being able to actually talk to a human at the IRS makes a massive difference. I'm still shocked at how well this worked after my previous frustrations.

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Luca Romano

•8M

If you can't get through the online verification, you can use the "Get Transcript by Mail" option instead. It takes about 5-10 days to arrive but doesn't require the same strict verification. Alternatively, you can file Form 4506-T and specify that you want the Wage and Income transcripts for your missing years. Another option is to try calling your previous employers' HR departments directly. Many larger companies have systems to provide past employees with W-2 copies, even from several years back. Sometimes this is faster than waiting for the IRS transcripts.

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