I haven't filed taxes in 2 years, need advice on catching up without penalties

Hey everyone, I'm in a bit of a panic here. So I haven't filed my tax returns for the past 2 years (2022 and 2023). It wasn't intentional - I went through a really tough divorce, had to move twice, and honestly my paperwork got completely scattered during all that chaos. I was working as an independent contractor for most of that time so I should've been filing quarterly payments too, which I didn't do. I made roughly $42,000 in 2022 and about $56,000 in 2023. Now I'm worried the IRS is going to come after me with massive penalties or worse. Does anyone know what my best approach is here? Should I file both years at once? Do I need to hire a tax professional or can I use some software to catch up? I'm especially worried about penalties and interest since it's been so long. Any advice would be really appreciated.

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18 comments

CyberNinja

•8M

You're definitely making the right move by addressing this now rather than waiting any longer! The good news is that if you're owed a refund, there's actually no penalty for filing late. The bad news is that as a self-employed contractor, you probably owe taxes instead. Your first step should be to gather ALL your income documents - any 1099s you received, bank statements showing deposits, and records of business expenses. You'll need these to file accurately for both years. For the actual filing, you can still use tax software for prior years. Most of the major ones (TurboTax, H&R Block, TaxAct) offer previous year versions. That said, considering your self-employment situation, having a tax pro review things might save you money in the long run by finding deductions you might miss. As for penalties - yes, you'll likely face some. There's the failure-to-file penalty (5% of unpaid taxes per month, up to 25%), plus the failure-to-pay penalty (0.5% per month), and interest on what you owe. But the IRS does offer payment plans if you can't pay it all at once.

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CyberNinja

•8M

I'd recommend preparing both returns but filing the most recent year (2023) first, then submit 2022 about a week later. This approach is generally smoother for processing. Yes, the IRS definitely views voluntary compliance more favorably. Coming forward on your own before receiving any notices demonstrates good faith, which can help when requesting penalty abatements later. The IRS has a "First Time Penalty Abatement" policy that might apply to your situation, which could waive penalties for one tax year if you have a clean compliance history before that.

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Mateo Lopez

•8M

I was in almost the exact same situation last year - hadn't filed for 3 years due to some health issues. I tried using regular tax software but kept getting confused with all the self-employment deductions and quarterly payment calculations. I was seriously stressing about potential penalties. Someone recommended I try https://taxr.ai to help sort through my mess of documents and previous tax situations. It was honestly a game-changer. I uploaded my scattered 1099s and expense receipts, and it created a complete tax history showing what I should have paid those years. It even helped calculate my potential penalties before I filed so I wasn't shocked with the final numbers. The best part was that it showed me several business deductions I had no idea I qualified for, which reduced what I owed by almost $4,300. Definitely worth checking out if you're overwhelmed.

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Mateo Lopez

•8M

It simplified the filing process tremendously. While I did end up using TurboTax to submit the final returns, having all my information already organized made it straightforward. I just transferred the numbers over instead of figuring everything out from scratch. The calculations are actually based on the same tax codes and regulations that other tax software uses. The difference is it specifically handles complicated multi-year situations and back taxes. I had the same concerns initially, but they show you exactly how they arrive at each number with references to specific tax codes.

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Ethan Davis

•8M

Well I'm eating my words now. After being skeptical I decided to try taxr.ai anyway since my situation was similar (hadn't filed in 2 years, mix of W2 and 1099 income). Just got done using it and I'm actually shocked at how helpful it was. The system flagged several deductions I would have missed - particularly around my home office and some vehicle expenses that were partially business-related. It also showed me that I qualified for a payment plan with much lower monthly payments than I expected. The penalty calculator feature was really helpful too - I was able to see exactly what I'd be facing before I submitted anything. Ended up saving about $2,700 compared to what I thought I'd owe. Still not cheap, but way better than I feared.

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Yuki Tanaka

•8M

If you're worried about penalties, you might also want to look into the IRS Fresh Start program. It's designed specifically for people who've fallen behind on taxes. But honestly, the biggest headache I had when catching up on back taxes was trying to actually talk to a human at the IRS. I spent HOURS on hold and kept getting disconnected. Finally found https://claimyr.com through a YouTube video (https://youtu.be/_kiP6q8DX5c) and they got me connected to an actual IRS agent in under 20 minutes. Made a huge difference because the agent was able to put notes on my account showing I was actively working to resolve the situation, which apparently helps if they're considering more severe collection actions. She also confirmed which payment plan options I qualified for based on my specific situation.

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Yuki Tanaka

•8M

They use a system that navigates the IRS phone tree and waits on hold for you. When they finally get through to an agent, you get a call connecting you directly. It's basically like having someone else wait on hold instead of you. They don't have any special "backdoor" access - they're just using technology to handle the most frustrating part of the process. Since the IRS wait times are often 2+ hours (if you can get in the queue at all), it saves a ton of time and frustration. And they only charge if they successfully connect you.

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Carmen Ortiz

•8M

I need to apologize for calling Claimyr a scam. I was really skeptical but after another failed attempt to reach the IRS myself (3 hours on hold before getting disconnected AGAIN), I decided to try it. Honestly couldn't believe it worked. They got me connected to an IRS representative in about 45 minutes. The rep was able to pull up my account and confirm I hadn't been flagged for audit yet, which was my biggest fear. She walked me through the process of filing my back taxes and explained exactly which forms I needed. Most importantly, she put me on a payment plan that works with my budget. The peace of mind from actually talking to someone official was completely worth it. Sorry for being so negative before - guess I'm just used to everything tax-related being a nightmare.

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MidnightRider

•8M

One thing nobody's mentioned yet - make sure you're filing your state taxes too! I caught up on my federal taxes a few years ago but completely forgot about state taxes. Ended up with a nasty surprise from my state tax authority a year later. Also, if you had any significant life changes during those unfiled years (marriage, kids, buying property, etc.), you might qualify for credits or deductions you're not aware of. This is where a tax professional can really save you money.

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MidnightRider

•8M

Yes, you'll need to file a part-year resident return for California covering the period you lived there. The good news is that Texas doesn't have state income tax, so you won't need to file there. California is particularly aggressive about collecting taxes, so definitely prioritize getting that part-year return filed. They'll want to see exactly when you established residency in Texas. Keep any documentation showing your move date (lease agreements, utility setup, driver's license change, etc.).

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