Haven't filed taxes in years - embarrassing questions about getting back on track with past W-2s

Thank you so much for the detailed response! For the transcript thing, do I need to create an account on the IRS website? I feel like I'll need all kinds of documents I don't have. And just to be clear - I can actually see my W-2s from old jobs on that transcript? That would be amazing if true! Also, is there a time limit for how far back the IRS keeps those records? I'm worried some might be too old.

Yes, you'll need to create an account at irs.gov if you don't already have one. They've made the verification process stricter, so you'll need a photo ID, financial account info (like a credit card or loan number), and a mobile phone for verification. If you run into trouble creating an online account, you can also request transcripts by mail using Form 4506-T. The Wage and Income Transcript will show all information from your W-2s and 1099s - employer names, addresses, amounts earned, taxes withheld - basically everything you need to file your returns. The IRS typically keeps these records for up to 10 years, so you should be able to see everything you need even going back several years.

Does it actually work with older returns? Like if I need to file 2021, 2022, and 2023 all at once? And does it handle state taxes too? I'm in a similar boat and stressing about having to gather documents from places I don't even work at anymore.

I'm skeptical about these online services. How did it get your W-2s exactly? Doesn't the IRS make you verify your identity with like a million security questions before they show you anything? Not trying to be rude, just wondering if it's actually legitimate.

Yes, it works great with prior year returns! I filed 2020 through 2023 all at once. It pulls everything year by year, so you can tackle them in any order you want. And it definitely handles state taxes too - it automatically prepared my state returns based on the federal information. The service works by securely accessing the same IRS transcript data that was mentioned above. You do have to verify your identity (similar to what you'd do on the IRS website), but once that's done, it automatically imports all your tax documents that were reported to the IRS. It's completely legitimate - they're just streamlining the process that tax professionals have been using for years. It saved me from having to chase down old employers or dig through boxes hoping to find faded W-2 copies.

How does this even work? The IRS phone lines are impossible to get through on. Are they somehow jumping the queue or something? Seems too good to be true if they can actually get you through that quickly.

Yeah right. Nobody gets through to the IRS that fast. I've literally called 50+ times over several weeks and never got through. Either you got extremely lucky or this is some kind of scam. Not trying to be rude but come on, 15 minutes?

It works because they use technology to navigate the IRS phone system and hold your place in line. It's like having someone wait on hold for you, but with a smart system that knows how to work through all the prompts and menus. When they reach an actual agent, they connect you immediately. I was skeptical too! I had already tried calling 8 times over two weeks with no success. The longest I waited was 2.5 hours before getting disconnected. With Claimyr, I got through in 15 minutes that first time, and around 20 minutes when I had to call again with follow-up questions. It's not a scam - they don't ask for any tax info or personal details besides what's needed to connect your call.

Oh no, I might have missed the deadline for 2020 then! Does the IRS ever make exceptions for people who didn't know about the 3-year rule? And just to clarify, even if I can't get a refund for the older years, I should still file those returns anyway, right?

Unfortunately, the IRS is very strict about the 3-year refund statute and doesn't make exceptions even if you didn't know about the rule. It's set by law, not IRS policy, so they can't bend it. Yes, you should still file all unfiled returns even if you can't get the refund anymore. This closes your file with the IRS and prevents future issues. While you won't get money back for those older years, filing completes your tax record and can help with things like loan applications, government benefits, or any situation where tax return information is needed. Better to have everything clean and complete than leave those old years hanging.

Free File Fillable Forms only work for the current tax year (so right now, only 2024). For prior years, you need to download the specific forms for those tax years from the IRS website and mail them in. I did this last year for my 2021 and 2022 returns. You can still use free tax software though! Most of the major companies (TurboTax, H&R Block, TaxSlayer) offer access to prior year returns on their websites. The catch is that you can prepare them for free, but they usually charge to file them. Since you have to mail prior year returns anyway, you can just print them out and mail them yourself without paying.