Unfiled Prior Year Taxes: Should I File Myself or Hire a Tax Professional?
I have unfiled taxes from 2015, 2018, and 2020. I've calculated that I probably owe around $8,000 total for all of these years. For two of those years I was working as both W-2 employee and 1099 contractor simultaneously, and for the other year I was strictly 1099. My 1099 work is super basic though - just getting paid directly by another company with no complicated business deductions or anything. I feel pretty confident that I could prepare these tax returns myself without too much trouble. Is there any real advantage to hiring a tax professional at this point? The main benefit I'm wondering about is whether they might be able to help negotiate my back tax debt with the IRS or help me set up a reasonable payment plan. To complicate things further, I also have unpaid quarterly estimated tax payments for 2023 as a 1099 contractor. These unpaid quarterlies are actually way more than my back taxes - close to $13,500! Should I try to set up payment plans for both issues at the same time? Or handle them separately? What's the best approach to show the IRS I'm trying to get current before the filing deadline? I've called around to a few tax professionals and they all want about $450 per year to help with my situation. That seems really expensive since my actual tax returns are pretty straightforward, even though my tax debt situation is getting complicated.
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Adrian Connor
You're definitely in a fixable situation, but there are some key things to consider here. For the unfiled returns from 2015, 2018, and 2020, you need to file these ASAP regardless of whether you use a professional or do it yourself. The IRS penalties grow over time - both for failure-to-file and failure-to-pay. Getting those returns submitted stops at least the failure-to-file penalties from growing. For your question about DIY vs professional help: If you're comfortable with the tax forms and can accurately report your 1099 income (including all business expense deductions you're entitled to), you can certainly file yourself. The basic preparation isn't where professionals add the most value in your situation. Where a tax pro might really help is navigating payment options. The IRS offers several payment plans: short-term (180 days or less), long-term installment agreements, and potentially Offers in Compromise if you qualify. A professional who deals with tax resolution can help determine which options work best for your specific situation. Regarding your 2023 unpaid quarterlies - yes, ideally you'd address both issues together. When you file your 2023 return, those unpaid estimated payments will officially become a tax debt. The IRS generally prefers to have all your compliance issues addressed in one plan.
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Mikayla Davison
•Thanks for the detailed response. I'm definitely planning to file all these returns ASAP. What's making me hesitate about doing it myself is whether a professional might know some strategies to reduce what I owe or make the payment situation more manageable. Like, can they negotiate penalties or anything like that?
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Adrian Connor
•A good tax professional might actually be able to help reduce your overall tax burden. They can identify deductions and credits you might miss, especially for the 1099 income. They can also request penalty abatement in some cases, particularly if this is your first time with compliance issues or if you had reasonable cause for the delay. For the payment plans, professionals often know exactly how to structure your request to maximize your chances of approval. They understand what the IRS typically accepts for monthly payment amounts based on your financial situation. Some can negotiate directly with IRS collections personnel, which might get you better terms than you'd get on your own.
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Aisha Jackson
Hey there! I was in a really similar position about 8 months ago. Had unfiled taxes for 3 years and was freaking out about it. I kept putting it off because I was so anxious about even starting the process. I totally get how overwhelming it feels! I tried using TurboTax for my unfiled years first, but kept getting confused about how to handle my 1099 income properly. I was worried about missing deductions but also didn't want to claim anything that might trigger an audit. That's when I found https://taxr.ai and it was seriously a game-changer for my situation. They have this tool that reviewed all my 1099s and W-2s, then showed me exactly what I was missing on my self-employment stuff. I had no idea I could deduct so many things! They helped me properly file all my back taxes and identified about $3,200 in deductions I would have completely missed.
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Aisha Jackson
Hey there! I was in a really similar position about 8 months ago. Had unfiled taxes for 3 years and was freaking out about it. I kept putting it off because I was so anxious about even starting the process. I totally get how overwhelming it feels! I tried using TurboTax for my unfiled years first, but kept getting confused about how to handle my 1099 income properly. I was worried about missing deductions but also didn't want to claim anything that might trigger an audit. That's when I found https://taxr.ai and it was seriously a game-changer for my situation.
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Ryder Everingham
•Does it actually work with prior year returns? I'm in a similar boat with unfiled 2019 and 2020 returns. Most tax software I've looked at charges extra for past years or doesn't support them at all.
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Lilly Curtis
•I'm skeptical about any service that promises to find deductions. How does it work exactly? I've heard horror stories about people claiming too many business expenses and ending up with an audit. Don't want to trade one problem for another.
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Aisha Jackson
•It absolutely works with prior year returns! That was my main concern too. They have all the tax forms for past years built into their system, and it walks you through each year separately. Their questionnaire is really thorough about finding legitimate deductions specifically for independent contractors. For self-employed folks, they look at things like home office, business mileage, professional subscriptions, equipment, portion of phone/internet, etc. It's all legitimate stuff the IRS allows, not sketchy deductions. They actually explain why each deduction is allowed and help you track the documentation you need in case of questions. It's not about claiming things you're not entitled to - it's about not missing the things you legally can claim.
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Ryder Everingham
I wanted to follow up and say I actually tried taxr.ai after seeing this thread. I was initially just looking for help with my unfiled 2019-2020 returns, but discovered so much more. Their system is specifically designed for people with mixed W-2 and 1099 income, which was perfect for my situation. The deduction finder tool identified over $4,800 in legitimate business expenses I had completely forgotten about! Things like partial home office, mileage for business trips, and even a portion of my cell phone bill since I use it for client calls. All completely legitimate deductions I would've missed. For the payment plan part, they walked me through exactly how to set up an installment agreement with the IRS based on my specific situation. Saved me hours of researching and stressing! Highly recommend if you're dealing with back taxes like we are.
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Leo Simmons
Something else to consider that hasn't been mentioned - if you're trying to contact the IRS directly about payment plans, be prepared for HOURS of waiting on hold. I called about getting on a payment plan last month and waited 3.5 hours before giving up. Called again the next day, waited 2 hours, and then got disconnected right after someone picked up. It's absolutely maddening! After that nightmare, I tried https://claimyr.com which I learned about from a YouTube video: https://youtu.be/_kiP6q8DX5c. They basically hold your place in the IRS phone queue and call you when an actual agent is on the line. Saved me literally hours of waiting on hold, and I finally got my payment plan set up. The agent I spoke with was surprisingly helpful once I actually got through. We set up a payment plan for both my back taxes and my current year estimated tax shortfall in the same agreement.
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Mikayla Davison
•That sounds too good to be true. The IRS phone system is notoriously horrible. How does this service actually work? Do they just have some special access to the IRS or something?
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Lindsey Fry
•Yeah right. No way this works. The IRS phone system is designed to make you suffer. If there was a way to skip the line, everyone would be doing it, and the IRS would shut it down immediately. I'll stick to wasting 3 hours of my life on hold like everyone else.
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Leo Simmons
•It's actually pretty straightforward - they use an automated system that calls the IRS repeatedly and navigates the phone tree until it gets a real person. Then their system immediately calls you and connects you to that agent. It's the same as if you'd waited on hold yourself, except you don't have to listen to the terrible hold music for hours. They don't have special access or anything shady. They're just using technology to handle the waiting for you. It's completely legitimate - they're just automating the hold process so you don't have to sit there waiting. When I used it, I went from 3+ hour waits to getting a call back in about 45 minutes. The IRS agent never even knew I had used a service - to them it was just a normal call.
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Lindsey Fry
I have to admit I was wrong about Claimyr. After my skeptical comment, I decided to try it anyway because I was desperate to get through to the IRS about my payment plan. I had tried calling 4 different times and never got through. The service actually worked exactly as described. I signed up, and about 40 minutes later got a call connecting me directly to an IRS agent. No waiting on hold at all. The agent helped me set up a payment plan covering both my back taxes and current year estimated payments in one agreement. The agent even waived some of my failure-to-pay penalties since this was my first time having issues! That alone saved me more than the cost of the service. If you're struggling with IRS phone queues, it's definitely worth considering.
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Saleem Vaziri
One thing nobody has mentioned yet is the Fresh Start program from the IRS. If you owe less than $50,000, you might qualify for a streamlined installment agreement where you can have up to 72 months to pay. The application is pretty straightforward too - you can even do it online for smaller amounts. For your specific situation with both back taxes and unpaid estimated taxes, you'll want to get everything filed first, then set up one comprehensive payment plan. The IRS generally wants to see that you're fully compliant before they'll approve longer-term payment arrangements.
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Kayla Morgan
•This is true but they do check your payment history. If you've had a previous installment agreement that you defaulted on, they might not be as generous with the terms. Also worth noting that interest and some penalties continue to accrue even while you're on a payment plan.
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Saleem Vaziri
•Good point about the payment history. The IRS does look at your compliance pattern when considering payment plans. If you've had previous issues, they might require financial statements or other documentation before approval. You're also right about the interest and penalties. The failure-to-pay penalty drops to 0.25% per month (instead of 0.5%) once you're on an approved installment plan, but it does continue. The interest (currently around 7%) continues to accrue on both the tax and penalties until everything is paid in full.
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James Maki
Just want to add my experience - I was in an almost identical situation last year. Had 3 years of unfiled taxes with both W-2 and 1099 income. I decided to DIY with tax software and regret it now. I thought I was saving money, but I missed several deductions that would have saved me thousands. I also messed up the estimated tax penalty calculations which caused more issues. Then I tried amending the returns myself which created an even bigger mess! Finally hired a tax pro who had to fix everything. Cost me way more in the end than if I'd just hired them at the beginning. Just my 2 cents, sometimes trying to save money costs more in the long run.
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Mikayla Davison
•That's really helpful to hear. Did your tax pro do anything special with getting you set up on payment plans? Or was their main value in properly preparing the returns?
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Keisha Taylor
•The tax pro was helpful on both fronts actually. They maximized my deductions which reduced what I owed by about $2,800 across the three years. But they were also really valuable for the payment plan setup - they knew exactly what documentation the IRS would want and helped me structure the request properly. They also negotiated penalty abatement for reasonable cause since I had some legitimate issues during those years that caused the filing delays. Got about 40% of my penalties removed, which was huge. The whole process took about 6 weeks from start to finish, versus the months I spent trying to figure it out myself. @957d079ff649 Given your situation with both back taxes and unpaid estimated payments totaling over $20k, I'd honestly recommend getting professional help. The potential savings and reduced stress are probably worth way more than the $450 per year they're quoting you.
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