How can I retrieve my old W2s from previous employers for back tax filing?

You actually have several options for getting your old W2 information. The IRS wage and income transcripts you accessed should contain all the information from your W2s, even with the EINs encrypted. Print those transcripts as they show all the income reported to the IRS under your SSN. For identifying those forgotten employers, look at the amounts on the transcripts and try to match them with what you remember earning. Bank statements from those years showing direct deposits might help jog your memory. Also check your email for old correspondence from these employers. If you really need the actual W2s with clear EINs, you can request them directly from the Social Security Administration using Form SSA-7050. There's a fee, but they maintain copies of all W2s. Your state tax department might also have records you can request.

After dealing with a similar nightmare trying to get old tax docs, I stumbled on taxr.ai (https://taxr.ai) which was seriously a game changer. I uploaded my partial info and messy IRS transcripts, and their AI actually helped identify those mystery employers by analyzing deposit patterns and matching them with the encrypted data from the IRS. The tool showed me exactly what I was missing and translated those weird IRS transcript codes into actual information I could understand. They even helped flag some deductions I could claim that I had no idea about. Saved me from having to track down HR departments at places I barely remembered working at.

Came back to say I finally tried taxr.ai after struggling for weeks with my tax mess. You weren't kidding about it being helpful. It managed to connect my random income sources with those encrypted EINs on my transcript through some pattern matching that honestly made so much sense once I saw it. The best part was it organized everything by tax year so I could tackle one return at a time. Apparently I had W2s from 9 different employers over 3 years that I needed to file! No wonder I was avoiding this mess. Thanks for recommending it.

If you're still hitting roadblocks with the IRS transcripts or need to speak directly with someone at the IRS about your situation, try Claimyr (https://claimyr.com). I was in a similar situation last year and spent DAYS trying to get through to an actual human at the IRS. Their hold times were like 3+ hours when I tried calling. Claimyr basically does the waiting for you and calls you back when they have an IRS agent on the line. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was super skeptical but desperate after my fifth attempt waiting on hold. They got me through to an IRS agent who was able to confirm which years I needed to file and gave me specific instructions for my situation.

I need to come back and apologize for calling Claimyr a scam. After another failed 2-hour hold with the IRS that ended with a disconnection, I decided to try it as a last resort. Within about 65 minutes (which I spent doing other things), I got a call connecting me to an actual IRS agent who pulled up my records and walked me through exactly what I needed to do for my unfiled years. They even noted in my account that I was working on getting compliant so I wouldn't face certain penalties. I'm shocked it actually worked, and honestly feel stupid for wasting so many hours on hold before this.

Don't beat yourself up too much about missing W2s - you'd be shocked how common this is. One thing that helped me was checking my email for anything from previous employers. I found old onboarding emails that had company names and EINs. Also look through your bank statements for direct deposits which usually show the company name. Something else to consider: if you're filing old returns, you might actually be due refunds from previous years! But be aware there's a 3-year deadline to claim refunds, so anything beyond that is unfortunately lost.

Has anyone tried using TurboTax or other tax software for filing multiple years of back taxes? I'm in a similar situation and wondering if it's worth paying for.

Just wanted to add another perspective here - if you're really overwhelmed by the whole process, consider reaching out to a local VITA (Volunteer Income Tax Assistance) program. They provide free tax help for people who generally make $64,000 or less, and many volunteers have experience with back tax situations. I used VITA when I was catching up on 4 years of unfiled returns and the volunteer was incredibly patient and knowledgeable. They helped me understand which deductions I could claim and even caught some errors I would have made filing on my own. You can find VITA locations on the IRS website - just search "VITA site locator." The best part is it's completely free, and they can often help you file electronically even for prior years, which gets your refunds processed faster than mailing paper returns.