Need help with deceased father who hasn't filed taxes in 17+ years - all cash income, no paper trail

Thank you for this detailed response. I had no idea I could request his tax transcripts - that's really helpful. Is there a specific type of tax attorney I should look for? And what happens if we simply can't determine his income for those years given the cash situation?

You'll want to look for a tax attorney who specializes in "back tax issues" or "unfiled returns" - ideally someone with experience handling estates. Many offer free consultations, so interview a few before deciding. If you can't determine exact income, you'll need to make good faith estimates based on whatever information you have - industry standards for his type of business, any partial records, lifestyle indicators, etc. Document your methodology carefully. The goal is to show reasonable effort to comply, even with limited information. In some cases, the IRS may accept returns with estimated income if they understand the circumstances, especially when the taxpayer is deceased and records are unavailable.

How exactly does it work? Can it really help when there's basically zero documentation? My mom was also a "cash only" person and I'm worried I'll be in this same situation eventually.

Sounds sketchy tbh. How can any software know what someone earned in cash years ago? The IRS themselves wouldn't even know that.

The tool works by using advanced data analysis to establish baseline patterns from the limited info you DO have. It can't create data from nothing, but it helps reconstruct reasonable estimates based on factors like location, business type, industry averages, and any partial records. It's actually not about "knowing" exactly what someone earned - it's about creating defensible estimates that satisfy the IRS's requirements when exact records don't exist. The IRS understands that in cases of deceased taxpayers, perfect documentation often isn't available. What they're looking for is a good faith effort to comply, which includes reasonable estimation methods when exact figures aren't available. The software helps document your methodology, which is crucial if the IRS ever questions the returns.

Does it actually work consistently? I've tried those "skip the wait" services before and they almost never work for government agencies.

This sounds like BS. The IRS phone system is designed to keep people waiting. There's no magic way to skip the line. If this worked, everyone would use it.

It's worked consistently for me through 3 different calls to different IRS departments. The service doesn't "skip" the line - it just waits in line for you and calls when an agent picks up. Think of it like having someone else sit on hold so you don't have to. The technology is pretty straightforward - they have an automated system that keeps redialing and navigating the phone tree until it detects a human voice, then bridges the call to your phone. For estate matters specifically, getting through to a human is essential since these cases are too complex for automated systems and often require explanation. Each time I've used it, I've received the callback within 15-45 minutes, depending on IRS wait times that day.

I hadn't heard of this program. Would this still apply even though he passed away? And how did you handle estimating income when there were no clear records?

Yes, it still applies for deceased taxpayers when the estate representative initiates the disclosure. The program essentially acknowledges that you're coming forward voluntarily before any IRS enforcement action. For estimating income, we used industry standard profit margins for his type of business, looked at his living expenses and assets acquired during those years, and made reasonable estimates. We documented our methodology carefully and explained the cash-only nature of his business. The IRS was actually surprisingly reasonable once they understood we were making a good faith effort. For some years, we used Form 8275 (Disclosure Statement) to explain our estimation methods. The key was being transparent about how we arrived at the figures rather than just putting random numbers.

He did own his house - bought it in the late 90s and paid it off around 2003 according to what he told me. But I can't find any mortgage paperwork. That's a good idea about property records though, I should check with the county assessor's office to see what they have. That might at least give me some baseline for what he was earning back when he qualified for the mortgage.