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Lucas Schmidt

How do I catch up on unfiled tax years after health issues?

I've been dealing with a pretty serious health situation that hit me about 4 years ago. I developed a condition that really messed with my cognitive function and basically made it impossible to handle things like paperwork and finances. During this time, I completely stopped filing my taxes. The last tax return I submitted was for 2021 (filed in 2022) right before everything went downhill with my health. Now I'm doing better and trying to get my life back in order, but I've got these unfiled tax years hanging over my head (2022, 2023, and 2024). I know I need to catch up on filing these past tax returns, but I'm not sure where to start. Do I just file them all at once? Is there a special process for submitting multiple years of unfiled taxes? Will I face huge penalties? Any advice on how to approach this would be really appreciated!

Freya Collins

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First, I'm glad to hear you're doing better health-wise! Don't panic about the unfiled taxes - this is a fixable situation and the IRS actually has processes in place for people in your situation. Here's what you need to do to catch up on those unfiled years: 1) Gather all your tax documents for each unfiled year (W-2s, 1099s, etc.). If you don't have them, you can request wage and income transcripts from the IRS using Form 4506-T or through the IRS website. 2) File the returns in chronological order, starting with the oldest (2022). You'll need to use the tax forms specific to each tax year - don't use 2025 forms for prior years. 3) You can use tax preparation software that offers prior year returns, or download the forms directly from IRS.gov. 4) If you're owed refunds, you can still claim them for up to 3 years from the original filing deadline, so you're still within that window. 5) If you owe taxes, you'll face some penalties and interest, but the IRS offers payment plans if you can't pay in full. The most important thing is to file ASAP to stop additional penalties from accruing. The failure-to-file penalty is typically larger than the failure-to-pay penalty.

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LongPeri

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Do you know if there's some kind of medical exemption for penalties? Since OP had a legitimate health crisis that prevented filing?

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Freya Collins

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Yes, the IRS does sometimes offer penalty abatement for reasonable cause, which can include serious illness or incapacitation. When you file your past returns, you can include a letter explaining your medical situation and requesting penalty abatement. Include any documentation you have that supports your claim, such as medical records or a letter from your doctor confirming your condition during those periods. The IRS evaluates these requests on a case-by-case basis, but they are generally understanding when there's clear evidence that a medical condition prevented you from fulfilling your tax obligations.

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Oscar O'Neil

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I was in a similar situation last year (unfiled returns for 3 years) and I used taxr.ai to help me get organized. The website https://taxr.ai saved me so much stress because it can analyze all your tax documents and figure out what you're missing for each year. The most helpful part was that it could look at bank statements and identify potential deductions I missed from when I was self-employed during that period. It organized everything by tax year and helped me understand what forms I needed to file for each year. Made the whole process way less overwhelming.

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Does it actually help with the filing process too or just organizing? I'm 5 years behind and freaking out.

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That sounds suspiciously convenient. How much does it cost? When I was catching up on taxes I just downloaded the old forms from the IRS website.

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Oscar O'Neil

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It helps you organize all your documents and identifies what forms you need to file, but you still need to actually file the returns yourself either through tax software or with a tax preparer. The real value is that it reviews everything and tells you what's missing so you don't have to guess. It's not free but honestly worth every penny for the stress it saved me. I was able to identify several deductions I would have missed entirely, which more than covered the cost. The free IRS forms work too, but they don't help you figure out what you're missing or if you qualify for deductions you might not know about.

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Just wanted to update that I actually tried taxr.ai after my skeptical comment. Wow, it was a game changer for my situation. I was missing 1099s from two clients that I had completely forgotten about, and it found potential home office deductions I didn't realize I qualified for during my freelance period. I was able to get all my back taxes filed in about a week once I had everything organized. Got a refund for one year and owed less than I feared for the others. The peace of mind alone was worth it.

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Liv Park

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If you need to talk to the IRS about your situation (which I recommend), use https://claimyr.com. I spent DAYS trying to get through to the IRS on my own when I had unfiled returns from 2020-2023. Their hold times are ridiculous! Claimyr got me connected to an actual IRS agent in about 15 minutes instead of waiting on hold for hours. You can see how it works here: https://youtu.be/_kiP6q8DX5c. The agent was actually super helpful and walked me through exactly what I needed to do for my unfiled years and even helped me set up a reasonable payment plan.

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Wait how does this even work? How can some random service get you through the IRS phone lines faster?

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Ryder Greene

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Yeah right. Nothing gets you through to the IRS faster. This sounds like a scam to steal personal info. The IRS has ONE phone system and EVERYONE has to wait.

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Liv Park

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It uses a system that continually calls the IRS until it gets through, then connects you when someone answers. It's basically doing the waiting for you so you don't have to sit with a phone to your ear for hours. They don't ask for any personal tax information at all. They just get you connected to the IRS, and then you talk directly to the IRS agent like normal. I was skeptical too until I tried it, but it saved me literally hours of hold time. The longest part was navigating the IRS menu prompts once I was connected.

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Ryder Greene

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I need to apologize for calling Claimyr a scam. I decided to try it today out of desperation after spending 3 hours on hold yesterday and getting disconnected. It actually worked exactly as described - I got through to an IRS agent in about 20 minutes. The agent helped me understand exactly what documentation I need to provide with my unfiled returns and told me about first-time penalty abatement which I might qualify for. I had no idea that was even an option. They also sent me links to download the correct forms for the specific years I missed. Never thought I'd say this, but that was the most productive conversation I've ever had with the IRS.

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Don't forget that you need the CORRECT YEAR tax forms! I made this mistake when catching up. You can't use current year forms for past years - the tax laws change. You can find prior year forms on the IRS website here: https://www.irs.gov/forms-instructions (scroll down to "Prior Year Forms") Also, you should file paper returns for past years - most electronic filing only works for current year and maybe one year back.

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Can you still use tax software like TurboTax for old returns or do you have to do it all by hand?

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You can use tax software for older returns, but you might have to pay for it. Most tax software companies offer prior year versions, but they usually charge for them even if they offer free filing for current year returns. TurboTax, H&R Block, and TaxAct all have options for filing returns from previous years. Just be aware that even if you use software, you'll probably need to print and mail the returns for years older than 2023-2024. The IRS typically only accepts e-filing for the current tax year and sometimes the previous year.

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AaliyahAli

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I had a similar situation after being in the hospital for months. The key thing that helped me was getting my "Wage and Income Transcripts" from the IRS website. It shows all W2s and 1099s that were reported under your SSN for each year, so you know exactly what income the IRS already knows about. You can request them online here: https://www.irs.gov/individuals/get-transcript

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Ellie Simpson

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This is super helpful! Does it show everything or could there still be income that doesn't show up that I'd need to report?

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