Should I file all of my back tax returns at the same time or separately?

I've been avoiding filing my taxes since 2018. I estimate I probably owe around $250,000 at this point. My yearly income is about $130,000, but I've been using most of it to financially support several family members who really needed help. I've finally realized I can't keep doing this - I need to address my own financial problems before I completely drown. Looking back, I know it's my fault for letting this situation get so out of hand. I always prioritized helping my relatives over my own financial health, and now I'm facing the consequences. I'm trying to figure out the best approach - should I file all these back tax returns simultaneously, or is there a better strategy? Is there any hope for my situation, or am I completely screwed at this point? I'm getting really anxious about potential penalties and how to even begin tackling this mess.

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18 comments

Ethan Scott

•8M

I'm a tax resolution specialist, and I see cases like yours pretty frequently. First thing - take a deep breath. Yes, this is serious, but you're definitely not "doomed." The fact that you're taking steps to address it now is really important. For back tax returns, I generally recommend filing them all at once rather than trickling them in. This gives the IRS a complete picture of your situation, which is helpful when negotiating payment plans or potential settlements. Make sure you're accurate with what you report - don't estimate or guess on these returns. Your next step should be looking into payment options. With a liability that size, you might qualify for an Offer in Compromise (which lets you settle for less than you owe) or an installment agreement. You might also consider whether you qualify for penalty abatement, which could significantly reduce what you owe.

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Ethan Scott

•8M

You don't need to have all the money ready when you file. The IRS knows most people with back taxes can't pay everything at once. When you file, you can immediately request an installment agreement or begin the Offer in Compromise process. As for bank levies or wage garnishments, these typically only happen after multiple notices and opportunities to arrange payment have been ignored. Since you're being proactive now, you can usually avoid these enforcement actions by staying in communication with the IRS and making arrangements before they resort to collections. The IRS would much rather work with you on a payment plan than go through the hassle of forced collections.

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Lola Perez

•8M

I was in a somewhat similar situation a few years ago (not quite as much owed, but several years unfiled). After trying to handle it myself and getting nowhere, I eventually used this AI tax assistant called taxr.ai that helped me organize all my documentation and create a plan. It analyzed my situation and helped me understand what forms I needed and the best approach for my specific circumstances. The thing that helped me most was that it could look at all my tax documents and give me a complete picture of what I was dealing with. Check out https://taxr.ai if you're feeling overwhelmed by the paperwork and organization. It helped me figure out exactly what I needed before I even talked to a resolution specialist, which saved me a ton of money in professional fees.

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Lola Perez

•8M

Yes, it can give you a pretty good estimate of what you owe including calculating penalties and interest. It has all the IRS penalty rates and formulas built in. You upload your documents (W-2s, 1099s, etc.) and it does the calculations. It was actually spot-on with my situation - only about $200 difference from what the IRS ultimately determined. Regarding accuracy with complex situations, I was skeptical too, but it's specifically designed for tax issues including back taxes. It doesn't replace a tax professional entirely, but it organizes everything so when you do talk to someone, you're prepared and can often reduce how much professional help you need. It saved me thousands in professional fees because I only needed specific advice rather than having someone start from scratch.

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Nathaniel Stewart

•8M

Just wanted to come back and say I tried https://taxr.ai after seeing it mentioned here. It was seriously helpful for getting my unfiled tax returns organized. I was able to upload all my scattered documents, and it generated complete tax returns for each year I missed. The penalty calculator was eye-opening but at least now I know what I'm dealing with. Already submitted my back returns and am working on a payment plan. Wish I'd known about this tool years ago before letting this pile up!

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Santiago Diaz

•8M

Something everyone here is missing - you're going to need to actually talk to the IRS at some point, and that's a nightmare right now. I tried calling for weeks about my back taxes and couldn't get through. Then I found Claimyr (https://claimyr.com) which somehow gets you past the IRS phone tree and actually gets an agent to call YOU back. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c This saved me literally days of being on hold. Once I actually got to talk to someone, I was able to set up a payment plan that worked for my situation. For someone with multiple years of unfiled returns like you, being able to actually speak with the IRS is going to be crucial.

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Santiago Diaz

•8M

The service basically navigates the IRS phone system for you and holds your place in line. When an agent becomes available, they connect the call to your phone. It's completely legitimate - they're just using technology to handle the tedious waiting part. For your situation with the payment plan, it would work perfectly. You just tell them which IRS department you need to reach, and they handle the rest. I was honestly surprised at how well it worked too, but it's just automating something that would take you hours to do manually.

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Riya Sharma

•8M

I need to eat my words from earlier. After getting nowhere with the IRS for weeks, I tried Claimyr out of desperation. Within 45 minutes I got a call back from an actual IRS agent. I was able to discuss my payment plan issues and got everything sorted in one call. I'm still shocked at how well it worked - saved me hours of frustration. For anyone dealing with complex tax situations like the original poster, being able to actually speak with the IRS quickly is invaluable.

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KaiEsmeralda

•8M

The entire process took about 14 months from start to finish. The first part - gathering all my documentation and filing the back returns - took about 2 months. Then I submitted the Offer in Compromise application, which took another 2 months to prepare properly with all the required financial information. After submission, the IRS review process took about 10 months, including some back-and-forth with the assigned officer who was evaluating my case. There were a couple of requests for additional documentation during that time. It wasn't quick, but considering how much I saved in the end, it was absolutely worth the wait and effort. Just be prepared for a marathon, not a sprint.

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