How to file multiple years of unfiled tax returns and handle back taxes?

What if my partner can't find their W-2s from previous employers? Some of them have gone out of business. Is there still a way to get that information?

You can absolutely still get that information even if the employers are out of business. The best approach is to request a Wage and Income Transcript directly from the IRS, which shows all information reported to the IRS including W-2s and 1099s. You can request this online through the IRS website by creating an account at IRS.gov, by phone, or by mailing Form 4506-T (Request for Transcript of Tax Return). For the unemployment compensation specifically, your partner can contact their state unemployment office to request a duplicate 1099-G if they don't have the original one that was issued.

How does taxr.ai handle situations where you have missing documents? Like if you can't find an old W-2 or 1099, does it help you figure out what to do?

I'm curious about this too. Did it actually help with figuring out what you owed, or did you still need an accountant to actually file the returns? Those back taxes are what I'm really worried about.

For missing documents, it actually has a really useful feature that helps identify gaps in your tax documentation. It analyzes what you've uploaded and compares it to what would be expected based on your employment history and previous tax situations. Then it provides a checklist of what's still missing so you know exactly what to request from the IRS or former employers. It definitely helped me figure out what I owed before I actually filed. The service calculated my potential tax liability for each year based on the documents I provided, including estimating penalties and interest. I still used a tax preparer for the final filing, but going in with all this information organized made the process much cheaper and faster since I wasn't paying the preparer to hunt down and organize all my documents.

Wait, you actually pay a service to call the IRS for you? I don't get it. Couldn't you just keep calling yourself? Seems like a waste of money when you already owe taxes.

How much does this service cost? I've literally spent HOURS on hold with the IRS only to have the call dropped. If this actually works it might be worth it...

You're not paying them to call for you exactly - you're paying them to navigate the IRS phone system and wait on hold in your place. When you call the IRS yourself, you often get a message saying call volumes are too high and to try again later, then they hang up on you. I tried calling over 20 times before finding this service. The value isn't just in having someone else call, it's in actually getting through when the IRS is actively preventing most calls from even reaching the hold queue. Once I actually spoke with an agent, they helped me set up my payment plan with terms I could actually afford, which ended up saving me money in the long run.

That's such a good point I completely overlooked! We're in California, so definitely have state taxes to deal with too. Would the process be similar for catching up on state returns?

The process for California is similar but has some key differences. You'll need to file the past state returns separately using California's specific forms for each tax year. California's Franchise Tax Board (FTB) has their own document retrieval system, penalties, and payment plans that are separate from the IRS. What's actually helpful is that California has an online system that's sometimes easier to navigate than the federal one. You can register for a MyFTB account to access wage information and other tax documents the state has on file. Their payment plans tend to be shorter than IRS plans though, usually 12-36 months instead of up to 72.

I'd be very cautious about those tax relief companies. What they're referring to is called an "Offer in Compromise" which is a legitimate IRS program, but most people don't qualify for it. These companies often charge thousands of dollars upfront with no guarantee of results. The IRS only accepts offers when they believe the amount offered is the most they can expect to collect within a reasonable time period. Your brother would need to prove significant financial hardship. Many of these companies take large fees and submit applications that get rejected anyway.

thanks for the info. he's been struggling with medical bills too so maybe he would actually qualify. do you know if people can apply for that offer in compromise thing without using one of those companies? I'm worried those radio ads are just scams like you're saying.