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.

Don't overlook the importance of addressing state taxes too! Many people focus only on federal tax delinquency and forget that state tax authorities can be equally aggressive in collections.

I want to echo what others have said about not panicking - you're taking the right step by addressing this now. As someone who works in tax resolution, I see situations like yours regularly, and they are absolutely manageable. One thing I'd add to the excellent advice already given: when you do start working with a tax professional, make sure they explain the "substitute for return" (SFR) process to you. If the IRS has been filing returns on your behalf for some of the missing years (using only the income they know about with no deductions), you'll want to file proper returns to claim any deductions you're entitled to and potentially reduce what you owe. Also, don't be surprised if your actual tax liability ends up being less scary than you're imagining. Many independent contractors significantly overestimate what they'll owe because they forget about legitimate business deductions - home office expenses, equipment, professional development, travel, etc. The key is to be thorough and honest in your reconstruction of those missing years. Your future self will thank you for taking action now rather than letting this drag on any longer.

I've been doing a similar strategy for about 18 months, overpaying by $10-15K annually. One thing I learned from my CPA is to keep detailed records of your income estimation process - not just the final numbers, but the reasoning behind them. What's helped me feel more confident is treating this as legitimate tax planning rather than a credit card hack. I actually do try to make reasonable estimates based on potential income scenarios, and the fact that I'm conservative with my projections (leading to overpayments) is perfectly acceptable tax behavior. The key insight my CPA shared is that the IRS cares more about good faith effort in estimation than perfect accuracy. As long as you can show you're making genuine attempts to estimate properly and not just throwing random large numbers at them, you should be fine. I keep a simple log of my quarterly estimation reasoning that would satisfy any inquiry.

I've been following a similar strategy for about 2 years now, overpaying by roughly $18K annually. One thing that's given me peace of mind is working with a tax professional who helped me establish a defensible estimation methodology. What we do is create quarterly projections that account for variable income scenarios - like potential bonuses, freelance work, or investment gains that might materialize. I document these projections each quarter, showing how I arrived at my estimated payment amounts. Sometimes the income materializes, sometimes it doesn't, but the important thing is having a reasonable basis for each payment. The processing fees (around 1.9%) are definitely worth it when you're hitting signup bonuses that can be 15-20% returns in just a few months. Just make sure you're not putting all your overpayments on one card or making it too obvious that you're manufactured spending. My advice would be to treat this as legitimate tax planning first, credit card optimization second. Keep good records, vary your amounts somewhat year to year, and make sure you can articulate why your estimates led to overpayments if ever asked. The IRS isn't going to penalize you for being conservative with your tax planning.

Don't forget that if you're due a refund from any of the years you didn't file, you only have 3 years from the original due date to claim it. After that, the money is gone forever. But if you OWE money, there's no time limit for the IRS to collect! Not fair but that's how it works.

I went through this exact same situation about two years ago - four years of unfiled returns with gig work income mixed in. The anxiety was eating me alive until I finally bit the bullet and dealt with it. Here's what I learned: The IRS actually wants to work with you more than you think. I ended up qualifying for First Time Penalty Abatement which wiped out a huge chunk of the penalties. The key is being proactive about fixing it rather than continuing to avoid it. For your income level and situation, you'll likely owe some back taxes but it won't be catastrophic. The failure-to-file penalties are the killer (5% per month up to 25%), but once you get those abated, you're mostly looking at the actual tax owed plus interest. My biggest regret was waiting so long to address it. Every month you wait, more interest accrues. I'd definitely recommend getting professional help - an Enrolled Agent was worth every penny for me. They knew exactly which forms to file and how to minimize the damage. You've got this! It's scary but totally manageable once you start the process.

I'm right there with you! Just requested a callback this morning and I'm already feeling that familiar anxiety. Based on what everyone's saying here, it sounds like we're in for quite a wait. I've been through this before and ended up waiting almost 36 hours for them to call back. The worst part is you can't really make any plans or go anywhere because you never know when that call might come. I've started keeping a notebook next to my phone with all my questions written down so I don't forget anything when they finally do call. Hang in there - we'll get through this bureaucratic nightmare eventually! 📞😤

I'm literally in the exact same situation right now! Just submitted my callback request about 2 hours ago and I'm already refreshing my phone constantly. Reading through everyone's experiences here is both comforting (knowing I'm not alone) and terrifying (realizing I might be waiting for days). The anxiety is real - I have so many questions about my claim and bills that can't wait much longer. Has anyone noticed if there are certain times of day when callbacks happen more frequently? I'm trying to figure out if I should expect a call during business hours only or if they sometimes call in the evenings too. This whole system really needs an overhaul! 😰