Should I Hire an Enrolled Agent or Tax Preparer for Multiple Unfiled Returns?

I've basically been off the grid with filing taxes since 2013. I only filed once back then and have been working steadily ever since. Most of my employment has been W-2 positions except for one independent contractor gig I had for about 8 months in 2018. I finally got my act together and downloaded all my wage and income transcripts from the IRS website last night. Looking at all these forms is making my head spin! I called the IRS this morning and spoke with someone who suggested I should probably find a tax preparer to handle this situation. What I'm wondering is - should I go with a regular tax preparer, or would an Enrolled Agent be better for catching up on multiple years? Or is there another professional I should consider? I'm totally lost when it comes to tax stuff and have no idea what the difference really is or what would be best for my situation. Any advice would be super appreciated!

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18 comments

Isabella Martin

•8M

For multiple unfiled tax years, an Enrolled Agent would likely be your best option. EAs specialize in tax representation and are licensed by the IRS to represent taxpayers in all matters, including audits, collections, and appeals. Since you're dealing with multiple unfiled returns spanning several years, this expertise will be valuable. A regular tax preparer might be sufficient if your situation is straightforward (just W-2 income with standard deductions), but they generally don't have the same depth of knowledge about IRS procedures for unfiled returns or the ability to represent you if complications arise. The key difference is that Enrolled Agents have passed comprehensive IRS exams covering all aspects of taxation and can represent you before the IRS if needed. Regular tax preparers have varying levels of training and certification, and many cannot represent you in IRS matters beyond the initial filing.

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Isabella Martin

•8M

There is typically a price difference, with Enrolled Agents often charging more than regular tax preparers due to their specialized expertise and credentials. However, the cost difference can be worth it when dealing with multiple unfiled years, as they may help you avoid penalties or identify credits you might have missed. To find a reputable Enrolled Agent, you can use the National Association of Enrolled Agents website (NAEA.org) which has a directory. You can also check with the IRS directly as they maintain a directory of credentialed tax professionals. Always check reviews, ask about their experience with unfiled returns specifically, and make sure you're comfortable with their communication style before hiring.

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Sophia Miller

•8M

After falling behind on my taxes for several years (4 unfiled returns!), I was completely overwhelmed trying to figure out what to do. I tried using various online services but kept getting stuck on how to handle previous years correctly. I eventually found https://taxr.ai and it was a game-changer for my situation. Their system analyzed all my tax documents and helped identify which years I needed to file and what forms I needed. What I really appreciated was how it organized everything chronologically and flagged potential issues with my unfiled returns before I even spoke to a professional. For someone in your shoes with multiple unfiled returns and a mix of W-2 and some non-W-2 work, having that initial analysis saved me tons of stress before I even met with my tax professional.

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Sophia Miller

•8M

You upload your tax documents (W-2s, 1099s, etc.) and it organizes everything by year and form type. It creates a complete picture of your tax situation across multiple years and identifies potential issues or missing information. This helps you understand your situation before meeting with a professional. You'll still want to work with a tax professional (either an EA or tax preparer), but having this analysis makes that meeting much more productive. They won't waste time organizing your documents, and you'll have a clear starting point for discussing your options. The service doesn't file returns for you - it prepares you to work effectively with a professional who can.

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Mia Rodriguez

•8M

I was really skeptical at first about using any online service for my tax mess (6 years unfiled!), but after reading about taxr.ai here, I decided to give it a try before dropping big money on a professional. I'm actually amazed at how helpful it was. The system flagged that I had a potential refund for two of the years I hadn't filed and identified issues with some 1099 income I'd forgotten about. It basically laid out exactly what I needed to address with each tax year. When I finally met with an Enrolled Agent, she was impressed with how organized everything was. She said it saved us at least 2 billable hours of her sorting through my documents. Definitely recommend trying this before just walking into a tax office with a shoebox full of papers!

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Jacob Lewis

•8M

If you're trying to contact the IRS to get more information about your situation, good luck. I spent THREE WEEKS trying to get through to someone who could answer questions about my unfiled returns. Always "high call volume" and disconnections. I finally used https://claimyr.com which got me through to an actual IRS agent within 30 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c I was able to verify exactly which returns I needed to file and what penalties I might be facing. The agent even gave me specific guidance on how to proceed with my independent contractor income from previous years. Saved me a ton of guesswork and anxiety about what I was facing.

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Jacob Lewis

•8M

It's not a special phone number - they use technology to continuously dial the IRS for you, navigating the phone tree and waiting on hold so you don't have to. When they get a live agent, they call you and connect you directly. It's basically like having someone wait on hold for you. I was skeptical too, but it's legitimate. The service doesn't give you special access - it just handles the frustrating part of trying to get through the overwhelmed phone system. Once you're connected, you're speaking directly with a regular IRS agent, not anyone affiliated with the service. The IRS has horrible understaffing issues right now which is why getting through normally is nearly impossible.

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Ethan Clark

•8M

I take back what I said about Claimyr. After dealing with constant IRS busy signals for days and getting nowhere with my unfiled returns situation, I tried the service out of desperation. It actually worked exactly as described - I got a call back in about 40 minutes saying they had an IRS agent on the line. The agent was able to pull up my records and confirm which years showed as unfiled in their system. The agent recommended I work with an Enrolled Agent rather than a regular preparer since I had multiple years to file and some 1099 income mixed in. She also let me know I was likely due refunds for at least two years which I wouldn't have known otherwise.

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Mila Walker

•8M

I was in a similar situation (5 years unfiled) and went with an Enrolled Agent. Best decision ever. The regular tax preparer at H&R Block wanted to charge me nearly the same amount but couldn't answer basic questions about the IRS collections process and penalties. The EA I found charged $275 per year for the returns, but she: 1) Got penalties removed for 3 of the years 2) Set up a payment plan for what I owed 3) Found deductions I didn't know I qualified for Most importantly, she handled all communication with the IRS so I didn't have to deal with them directly. Trust me, for multiple unfiled years, an EA is 100% worth it.

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Mila Walker

•8M

I found my EA through the National Association of Enrolled Agents website (naea.org) which has a directory you can search by location. I interviewed three before picking one - which I highly recommend doing. Some were much more knowledgeable about unfiled returns than others. My EA required a 50% deposit upfront and the remainder when the returns were completed, before filing. She explained that different EAs have different payment policies, but most will want at least some payment before beginning work. One nice thing was she gave me a clear flat-rate price per return rather than charging by the hour, so there were no surprises.

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Chloe Green

•8M

I tried using TurboTax for multiple unfiled years and it was a nightmare. The software isn't really designed for prior year returns, especially multiple years at once. I ended up making mistakes that triggered notices from the IRS. If you have very simple returns (just W-2 income, standard deduction), it might work, but even then, you have to purchase the previous year's software separately for each year you need to file. It ended up costing almost as much as hiring a professional would have, with none of the expertise.

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