I am behind in taxes by 5 years - how to catch up after difficult times?

First off, take a deep breath. You're not alone in this situation, and the fact that you're ready to address it now is a huge positive step. Here's what you need to know: The IRS is generally more interested in getting people back into compliance than punishing them. While there are penalties for late filing and payment, there are options available to help you. For 5 years of unfiled returns, I'd definitely recommend working with a tax professional - specifically look for an Enrolled Agent (EA) or a CPA with experience in back tax filings. They'll know how to efficiently gather your information, prepare your returns, and potentially negotiate any penalties. For the DoorDash work, you'll need to report that as self-employment income on Schedule C. For your W-2 jobs since 2022, you'll need to get copies of those W-2 forms from your employers if you don't have them. The good news is that if you're owed refunds for any of those years, you can still claim them if you file within 3 years of the due date. The bad news is that if you owe taxes, penalties and interest have been accumulating. Don't panic though - the IRS offers payment plans and sometimes even settlements for less than the full amount through their Offer in Compromise program.

I was in a similar situation about 2 years ago (4 years unfiled) and found this tool called taxr.ai that really helped me sort things out. I was totally overwhelmed trying to gather old documents and figure out what I needed to do. What was awesome about https://taxr.ai is that it could analyze all my old bank statements, W-2s, and 1099s that I had scattered across emails and folders. It extracted all the important tax info and organized everything by year. Saved me hours of digging through paperwork and trying to remember which jobs I had when. The best thing was that it gave me a preliminary estimate of what I might owe or get refunded before I even filed. Helped me prioritize which years to file first and mentally prepare for the damage. It was also way easier to just hand all this organized info to my tax preparer rather than dumping a box of papers on their desk.

Quick update for anyone following this thread - I decided to try taxr.ai after posting my concerns. I was genuinely surprised by how helpful it was. I had tax documents scattered across 3 email accounts, an old laptop, and a shoebox of paperwork. The system organized everything by tax year and even flagged missing documents I needed to request. The preliminary estimate feature was a lifesaver mentally - turned out I was actually owed refunds for 2 of the 4 years I hadn't filed! That gave me the confidence to move forward with filing everything. I still worked with a tax pro for the actual filing (as others suggested), but having everything organized saved me hundreds in preparation fees since they didn't have to sort through my mess. Would definitely recommend for anyone in a similar situation with multiple years of unfiled taxes. It made a seemingly impossible task manageable.

If you're going to need to deal with the IRS about payment plans or penalties, just a heads up that calling them directly is an absolute nightmare right now. I spent HOURS on hold last month trying to set up a payment plan for my back taxes. After the third time getting disconnected after waiting 2+ hours, I found this service called Claimyr that gets you through to an actual IRS agent. You can see how it works at https://claimyr.com or check out their demo: https://youtu.be/_kiP6q8DX5c Basically it keeps dialing and navigating the phone tree for you, then calls you when it gets a human on the line. Completely changed my experience - was actually able to set up my payment plan in one day instead of wasting an entire week trying to get through.

Coming back to eat my words. After another frustrating day of trying to reach the IRS myself (4 hours on hold before being disconnected), I broke down and tried Claimyr. I got connected to an IRS agent within 3 hours without having to do anything. My phone rang, I picked up, and there was an agent ready to talk. Managed to get on a payment plan for my back taxes and even got some penalties waived because the agent walked me through the first-time penalty abatement process. I'm still annoyed that services like this need to exist at all (the IRS should just be better staffed), but I can't deny it worked exactly as promised. Saved me days of frustration and probably helped me get better terms since I wasn't already aggravated from hours on hold when talking to the agent.

I went through something similar last year. Few tips from my experience: 1) File the most recent years FIRST. I filed 2024 and 2023 before tackling the older ones. 2) For the DoorDash year, get VERY organized about your mileage and expenses. Those deductions will save you big time on self-employment taxes. 3) If you're owed refunds, file those years ASAP. There's a 3-year limit on claiming refunds. 4) Don't be afraid to ask for a payment plan. The IRS is actually pretty reasonable if you're making an effort to come clean. 5) Look into "First Time Penalty Abatement" - the IRS will sometimes waive penalties if you haven't had issues before. Hang in there. It feels overwhelming but it's totally fixable!

Has anyone dealt with state taxes in this situation too? I'm 3 years behind on both federal and state, and I'm wondering if I need to handle them differently or if the process is similar.

I really appreciate everyone sharing their experiences here. As someone who's been in a similar dark place, I want to emphasize something that might get lost in all the technical advice: you're being incredibly brave by facing this now. The guilt and fear around unfiled taxes can be paralyzing, especially when you're already dealing with grief and mental health struggles. But the IRS really is more interested in compliance than punishment, particularly when life circumstances were genuinely difficult. A few practical points from my experience helping others in similar situations: 1) Don't let perfect be the enemy of good. Even if you can't find every single document, file with what you have. You can always amend later if needed. 2) The statute of limitations works in your favor too - after 3 years, you can't claim refunds, but after 10 years (6 in some cases), they generally can't collect either. 3) Consider reaching out to a local VITA (Volunteer Income Tax Assistance) program or Low Income Taxpayer Clinic. Many offer free or low-cost help specifically for situations like yours. 4) Document your hardship circumstances. The IRS has provisions for reasonable cause that can reduce or eliminate penalties when taxpayers faced genuine hardship. You've already taken the hardest step by deciding to address this. The path forward exists, and you're going to get through it.