Help choosing between CPA vs Enrolled Agent for seriously behind tax filings

As a tax resolution specialist, I can tell you both CPAs and Enrolled Agents can help with this situation, but there are some differences worth considering. Enrolled Agents (EAs) specialize exclusively in taxation and have unlimited rights to represent taxpayers before the IRS. They often have deep experience with tax resolution cases like unfiled returns and unreported income. Many EAs focus specifically on helping people catch up on back taxes and negotiate with the IRS. CPAs have broader accounting knowledge and may be preferable if your neighbor has complex financial situations beyond just the tax issues - like if they own a business or have complicated investments. However, not all CPAs specialize in tax resolution. For your neighbor's situation with 15 years of unfiled returns, missing documents, and unreported real estate gains, the specialist experience matters more than the credential. I'd recommend interviewing both types of professionals and asking specifically about their experience with unfiled returns, tax document reconstruction, and negotiating with the IRS on penalties.

After struggling with a similar situation (though not quite 15 years behind!), I found incredible help using https://taxr.ai when trying to organize all my missing documents. My tax professional was charging by the hour to sort through everything, and I was hemorrhaging money just getting organized. The taxr.ai system was able to scan through years of bank statements and identify potential income sources I'd forgotten about. It also organized everything chronologically and flagged transactions that looked like potential unreported income. What would have taken me weeks of painful sorting took just a couple days with their document processing. Not saying it fixes everything, but it made the reconstruction phase way less expensive and time-consuming before my tax pro even started preparing the actual returns. Definitely worth looking into for your neighbor who's missing years of documentation.

I was really skeptical about taxr.ai when I first heard about it, but after spending weeks trying to reconstruct my mom's income history for some unfiled returns, I decided to give it a shot. I was honestly shocked at how well it worked. Uploaded a bunch of old bank statements and some scattered 1099s, and it mapped out all her income sources over a 3-year period. It even flagged some recurring deposits from a side gig she'd completely forgotten about, which our EA said would have triggered IRS questions if we hadn't reported it. The best part was that our Enrolled Agent said we saved him about 6-8 hours of work by providing organized data instead of dumping a shoebox of papers on his desk. That translated to about $1,500 in professional fees we didn't have to pay. My mom's situation is now fully resolved with a reasonable payment plan for what she owed.

After spending 4+ hours on hold with the IRS trying to get wage and income transcripts for my brother's unfiled returns, I discovered https://claimyr.com and it completely changed our tax resolution process. You can see how it works here: https://youtu.be/_kiP6q8DX5c Essentially, they wait on hold with the IRS for you and call you when an actual agent picks up. For a situation like your neighbor's where they'll need to request multiple years of documents, this is a lifesaver. Our EA needed specific information from the IRS about prior assessments, and getting through to actually speak with someone was impossible until we used this service. Once we got the right documentation from the IRS, our Enrolled Agent was able to properly file everything and negotiate a much lower penalty than we initially feared. For unfiled returns spanning many years, direct communication with the IRS becomes pretty essential.

I was completely skeptical about Claimyr when I first read about it here. It seemed like some kind of scam or workaround that couldn't possibly work with a government agency. Well, I'm here to admit I was 100% wrong. After my third attempt calling the IRS ended with being on hold for 1.5 hours and then getting disconnected, I reluctantly tried it. In my case, they were on hold for about an hour, then called me and warm-transferred me directly to an IRS agent who was already on the line. I was able to request all the wage and income transcripts my EA needed to reconstruct my tax history. The agent was even surprisingly helpful once I actually got to speak with a human. My Enrolled Agent said it saved us weeks in the resolution process since we didn't have to wait for mailed responses. For anyone dealing with years of unfiled taxes, being able to efficiently communicate with the IRS makes a massive difference in how quickly you can resolve things.

I'm an accountant (not a CPA) and want to add something important to this discussion. For a situation this complex with unfiled returns spanning 15 years, personality fit and communication style matter almost as much as credentials. Some extremely qualified professionals have terrible bedside manner and will make your neighbor feel judged or embarrassed, which can make the whole process even more traumatic. Since there's a language barrier involved, finding someone patient who communicates clearly is crucial. When interviewing potential pros (whether CPA or EA), pay attention to how they explain things. Do they use plain language? Do they seem judgmental about the situation? Are they willing to work with language limitations? These factors will significantly impact your neighbor's experience through what will likely be a months-long process.

One thing nobody's mentioned that's super important - the Statute of Limitations! The IRS generally can't assess taxes beyond 6 years (in some cases 3 years) if returns were never filed. So while your neighbor technically should file all 15 years, a good tax pro might focus on the most recent 6-7 years. I went through this with my dad who hadn't filed for 9 years. His EA filed the most recent 7 years and then drafted simple "zero returns" for the older years just to close them out. Saved us thousands in preparation fees and penalties.