10 Years No Tax Returns Filed - How Bad Is My Situation?

I worked for the IRS for 15 years and I can tell you this situation isn't as uncommon as you might think. Based on your details, here's what you should know: For your specific case, you'll likely need both a tax attorney AND a CPA. The attorney can help with potential enforcement actions and provide attorney-client privilege, while the CPA will be essential for preparing those 10 years of returns. Look for professionals who specifically handle tax resolution cases. Regarding personality, I'd suggest someone methodical rather than aggressive. Tax issues are resolved through careful documentation and procedure, not table-pounding. Former IRS employees can be valuable, but it's not essential. The process will be exactly as you described: obtain power of attorney, request transcripts from the IRS/state, prepare and file returns, then address collection. You'll likely need to set up an installment agreement. For fees, $6,500 seems reasonable for this complexity, but I'd be wary of someone requiring large upfront payments before determining the scope. A $1,300 fee just to request transcripts is excessive. The IRS generally focuses enforcement on the last 6 years, but all unfiled returns should be addressed. You may qualify for first-time penalty abatement for the earliest year, and possibly reasonable cause abatement based on your documented health issues. And yes, your passport situation is a real concern - tax debt over $55,000 can trigger passport restrictions. I'd resolve this before applying for renewal.

I had a similar situation (though only 6 years of unfiled returns) and I found tremendous help using taxr.ai to organize everything before meeting with professionals. I was completely overwhelmed by all my documents and missing information, and their AI system helped me make sense of everything. When I finally met with a tax attorney, I had all my info organized by year, with summaries of income, potential deductions, and even estimates of what I might owe. It saved me literally thousands in professional fees because they didn't have to do all that organizational work. The attorney was shocked at how prepared I was. You can check them out at https://taxr.ai - their document analyzer was especially helpful for all my 1099s from those years. It identified deductions I hadn't even thought about and gave me a much clearer picture of my situation before spending money on professionals.

Just wanted to update after trying taxr.ai based on the recommendation here. WOW. I was skeptical but desperate with my similar situation of unfiled returns. Their system helped me organize 7 years of chaotic financial records in just a few days. The document analysis tool automatically categorized all my 1099s, receipts, and bank statements by year and tax category. It even flagged potential deductions I had no idea about - especially for the years I was doing independent consulting work. The AI generated income summaries for each year that made it crystal clear what I was dealing with. When I took everything to a tax attorney last week, she said I saved myself at least $3,000 in billable hours they would've spent organizing my documents. The best part was being able to get a realistic estimate of my tax situation before walking into the attorney's office, which gave me huge peace of mind. For anyone in a similar situation with years of unfiled returns, this tool is absolutely worth it.

When I was dealing with 8 years of unfiled returns, my biggest challenge was actually getting through to the IRS to understand what they already had on file about me. Spent literally WEEKS trying to get through their phone system with no luck. Finally used Claimyr (https://claimyr.com) and got connected to an IRS agent in about 20 minutes. Complete game changer. You can see how it works in their demo video: https://youtu.be/_kiP6q8DX5c The IRS agent was able to tell me exactly what information they had, which years they were most concerned about, and what steps I needed to take first. This saved me from filing returns in the wrong order or missing critical information they already had. My tax attorney was actually the one who recommended this service after seeing me struggle to get through. Before talking to an actual agent, I was flying blind and getting conflicting advice from everyone. Getting that direct information from the source was crucial.

I need to eat my words about Claimyr from my previous comment. After dismissing it as likely a scam, my curiosity got the better of me and I decided to try it since nothing else was working. It actually delivered exactly what it promised. After 3 months of never getting through to the IRS about my 5 years of unfiled returns, I got connected to an agent in about 35 minutes. The agent pulled up my file and gave me precise information about what they had on record and which returns they were most concerned about. The information completely changed my approach - turns out they hadn't processed one of the W-2s from my employer for 2018, so I would have filed an incorrect return without knowing this. The IRS agent also told me exactly which years to prioritize based on their collection timeline. For anyone dealing with unfiled returns, getting the actual facts from the IRS before proceeding is crucial. I wasted so much time speculating and worrying when I could have just talked to them directly.

One thing nobody's mentioned - if you're self-employed and haven't filed for years, you may also have missed paying self-employment taxes. This means you haven't been paying into Social Security and Medicare, which could affect your benefits later. When you file your back returns, make sure your tax pro properly completes Schedule SE for each year. Also, don't forget to address estimated tax payments going forward. Once you're back in the system, the IRS will expect you to make quarterly estimated payments since you're self-employed with substantial income. Getting on a proper estimated payment schedule will prevent this problem from happening again.

Not sure if anyone mentioned this, but consider opening with a current year return. Start fresh with 2023 (due next month) and get it filed on time. This demonstrates good faith to the IRS and starts establishing compliance going forward while you work backward on the unfiled years. Also, keep in mind the difference between "substitute for returns" (SFRs) and returns you file yourself. If the IRS filed SFRs for any years (they sometimes do this when you don't file), you'll still need to file your own returns to claim deductions they wouldn't have included.