Help! Need to file 10 years of back taxes and don't know how to start

3 This is super helpful! I'm curious though - will the IRS come after me for all those years I didn't file? I'm really worried that once I start this process, they'll hit me with massive penalties for ALL the years I missed. Also, can I really just start with the most recent 6 years and be done with it? That seems too good to be true.

8 The IRS generally focuses on the last 6 years for bringing taxpayers into compliance, so yes, that's typically all you need to file to get current. They have limited resources and usually don't go back further unless there's suspicion of fraud or very large amounts owed. As for penalties, they're usually a percentage of what you owe. If you're due refunds for some years, there are no penalties for those years (though you can only claim refunds from the last 3 years). For years you owe taxes, there are failure-to-file and failure-to-pay penalties, but the IRS offers various relief programs. Once you start filing, you can request penalty abatement through their First Time Penalty Abatement program if you have a clean compliance history before the delinquent years.

12 That sounds promising but I'm skeptical. Did you still need an accountant after using it? I'm in a similar boat but my situation includes some 1099 work and a year where I withdrew from my 401k. Would it handle something more complicated like that?

19 How much does taxr.ai cost? Their website doesn't seem to have clear pricing and I'm worried about getting hit with a big bill after I've already uploaded all my info.

17 I actually didn't need an accountant after using it, though they do give you the option to connect with one if your situation is particularly complex. For your situation with 1099 work and a 401k withdrawal, it would absolutely handle that - those are common tax situations the system is designed for. It actually helped me with some 1099-MISC income I had forgotten about that showed up on my transcript. Regarding pricing, they use a "pay what you can" model based on your tax situation complexity. You get to see what they recommend before committing, and there are no surprise charges. I found it extremely fair for the peace of mind it provided, especially compared to what tax pros were quoting me for all those years of returns.

14 Wait, this is an actual service? So they just... wait on hold for you? And then call you when someone answers? That sounds too good to be true. How do they even do that legally? Has anyone else tried this?

19 Sounds like a scam to me. Why would you need a service to call the IRS? Just keep calling yourself and eventually you'll get through. Plus, giving some random company your personal tax details seems like a terrible idea. Hard pass.

6 Yes, they literally wait on hold so you don't have to! It's completely legal - they're just connecting you with the IRS, not impersonating you or accessing your personal information. They use a call system that maintains your place in line and then connects you directly when an agent answers. It's similar to the callback systems that some companies use, except it works with agencies that don't offer that feature. I was skeptical too until I tried it. I had already spent about 9 hours across multiple days trying to reach someone at the IRS with no success. With Claimyr, I got connected to an actual IRS representative within a couple hours of requesting the call. They don't ask for your personal tax details - they're just getting you connected to the IRS. You only share your information directly with the IRS agent when they call you.

1 Oh geez I hadn't even thought about state taxes! Do you know if Missouri has the same 6-year lookback period as the IRS? Or do I need to file all 10 years with the state?

22 Missouri generally follows the federal statute of limitations, so the 6-year lookback period is similar. However, there are some important differences. Missouri's Department of Revenue can be a bit more aggressive about collecting on older debts than the IRS in some cases. The good news is that Missouri offers voluntary disclosure programs that might help reduce penalties if you come forward voluntarily before they contact you. I'd recommend checking the Missouri DOR website or calling them directly after you get your federal situation straightened out. In my experience, state tax agencies are actually easier to reach by phone than the IRS.

8 Most of those "pennies on the dollar" tax relief companies are extremely misleading. What they're referring to is the IRS Offer in Compromise program, which is legitimate but has very strict qualification requirements that most people don't meet. These companies often charge thousands upfront with no guarantee of results. The reality is that if you have assets or a decent income, you likely won't qualify for significant reductions. The IRS has standard formulas they use to determine eligibility. You're better off working directly with the IRS or hiring a reputable local tax professional who charges reasonable fees. The IRS provides payment plans that most people can qualify for without needing a special "tax relief" company.