I've never filed taxes before - what happens now and what should I expect?
Title: I've never filed taxes before - what happens now and what should I expect? 1 I'm 28, single with no kids or property - basically nothing to my name except my regular job that provides W-2s. For various personal reasons I'd rather not get into, I've never filed taxes before. Not a single return. But I'm trying to get my life in order now and know I need to address this tax situation. I'm honestly terrified about what might happen. Will I owe a ton of money to the IRS? Is there any chance I could go to jail for not filing? My anxiety is through the roof just thinking about approaching this whole mess. I don't even know where to start or what to expect when I finally face this.
24 comments


Edison Estevez
8 You're taking a great first step by addressing this now! The good news is that if you've been a W-2 employee, your employer has likely been withholding taxes from your paychecks already, which means you might actually be owed refunds for past years rather than owing money. First, don't panic about jail time. The IRS rarely pursues criminal charges for non-filing unless there's evidence of fraud or deliberate evasion. For someone in your situation who's voluntarily coming forward, they're much more interested in getting you compliant. You should start by gathering all your W-2s from previous years. If you don't have them, you can request wage transcripts from the IRS by creating an account at IRS.gov or using Form 4506-T. Then you'll need to file returns for at least the last 6 years (though all unfiled years would be ideal). Consider using a tax professional who specializes in back taxes to help navigate this - many offer free consultations to assess your situation first.
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Edison Estevez
•3 Thank you for the reassurance, I'm feeling a bit better. But I don't have any of my old W-2s. Is there a limit to how far back I need to file? And would tax software work or do I really need a professional?
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Edison Estevez
•8 For missing W-2s, the IRS can provide wage transcripts going back several years, which will show what your employers reported. The IRS generally focuses on the last 6 years for unfiled returns, though technically there's no statute of limitations on unfiled returns. While tax software could work for simple situations, I'd recommend at least an initial consultation with a professional given your multiple unfiled years. They can help identify if you're due refunds (which you can only claim within 3 years of the due date) or if you'll owe, and might save you more than their fee costs. Many offer free initial consultations to assess your situation.
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Edison Estevez
12 I was in a similar situation a few years back (had 4 years unfiled) and was completely overwhelmed. What helped me most was using https://taxr.ai to analyze my situation. You upload your W-2s or wage transcripts and it shows you which years you're likely due a refund for and which you might owe on. Helped me prioritize which years to tackle first. The tool estimates penalties too, which was huge for me mentally - knowing the actual numbers instead of the scary ones in my head. Plus it shows which years you can still claim refunds for (only 3 years back) vs. which ones you might want to consider the IRS "first-time penalty abatement" option.
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Edison Estevez
•15 How accurate was it compared to what you actually ended up owing/getting refunded? I'm nervous about using online tools with my sensitive tax info.
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Edison Estevez
•4 Does it work if you don't have all your W-2s? I've moved like 5 times and definitely don't have all mine.
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Edison Estevez
•12 It was surprisingly accurate for me - within about $50-100 of the final numbers on each return. I ended up getting refunds for 3 of my 4 unfiled years which the tool correctly predicted. You don't need your actual W-2s - that's the best part. You can use the wage transcripts from the IRS (which show all the same info) by requesting them first from the IRS website, then uploading those to the tool. It's designed specifically for people who don't have all their original documents. The site uses the same security standards as banks, if that helps with the privacy concern.
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Edison Estevez
4 Just wanted to update after trying taxr.ai that the previous commenter mentioned. It was actually really helpful for my situation. I was able to see that I'm likely owed refunds for 2 of the 3 most recent years I didn't file! The older years show I might owe some penalties, but way less than the scary numbers I had in my head. The tool even generated a letter I can send requesting first-time penalty abatement which apparently has a high success rate. Feeling WAY less anxious now that I have actual numbers to work with instead of my imagination running wild.
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Edison Estevez
19 One crucial thing nobody's mentioned - you really need to get through to someone at the IRS before you start filing old returns. They might already have substitute returns filed for you which changes the whole process. I tried calling for WEEKS and could never get through until I used https://claimyr.com - they have a service where they wait on hold with the IRS and call you when an agent picks up. There's even a video showing how it works: https://youtu.be/_kiP6q8DX5c. Saved me literally hours of hold time. The IRS rep confirmed they had filed substitute returns for me for 2 years, which I wouldn't have known about otherwise and would have messed up my catch-up filing strategy.
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Edison Estevez
•5 Wait, the IRS files returns for you if you don't file? I didn't know that was a thing. Are those usually accurate?
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Edison Estevez
•22 This sounds like a scam. Why would I pay someone just to wait on hold? Couldn't you just put your phone on speaker and do something else while waiting?
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Edison Estevez
•19 The IRS can file what are called "Substitute for Returns" but they're usually not in your favor - they don't include most deductions or credits you'd be eligible for. They typically only do this for people with significant income reported on W-2s or 1099s who haven't filed for years. I tried the speaker phone approach many times, but the IRS disconnects calls after 2+ hours sometimes, and their callback feature is almost never available. I wasted entire days trying. With Claimyr, I got through in my first attempt and didn't have to disrupt my workday constantly checking if someone had picked up yet.
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Edison Estevez
22 I need to apologize for my skeptical comment earlier. I actually broke down and tried Claimyr after spending 3 days trying to get through to the IRS myself. Got a call back within 70 minutes when I'd previously been disconnected four times after waiting 2+ hours each time. The IRS agent confirmed they hadn't filed substitute returns for me yet but were about to start the process next month. Now I can file my back returns myself before that happens. Saved me a huge headache and potentially a lot of money since their substitute returns wouldn't have included my education credits.
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Edison Estevez
17 I used to work in tax preparation, and I just want to emphasize something important: the IRS is MUCH more accommodating when you come forward voluntarily versus them having to chase you down. They have payment plans available if you do end up owing, and the first-time penalty abatement program can eliminate a significant portion of penalties if you have a reasonable explanation. For someone with just W-2 income who's likely had taxes withheld already, there's a good chance you might even be due refunds for some years! You can only claim refunds within 3 years of the filing deadline though, so don't delay any longer.
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Edison Estevez
•3 Do you know if they ever waive the penalties completely? I'm so worried about ending up in debt I can't manage.
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Edison Estevez
•17 Yes, they absolutely can waive penalties completely in many cases. The IRS has a "First Time Penalty Abatement" policy that often removes penalties for the first time you have an issue, if you have a clean compliance history before that. You just need to ask for it - many people don't know to request this. Even if you do end up owing some money, the IRS offers payment plans with very reasonable terms. For smaller amounts (under $10,000), it's usually a very simple process to set up. They're truly more interested in getting people back into compliance than punishing them, especially when someone comes forward voluntarily like you're doing.
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Edison Estevez
2 One thing I haven't seen mentioned - double check if your state requires tax filings too! I fixed my federal situation but completely forgot about state taxes and ended up with a separate headache there.
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Edison Estevez
•10 Great point! I just dealt with this last year. Some states are more aggressive than the IRS about pursuing unfiled returns, too. I had to file 4 years of California returns after moving out of state and it was actually more complicated than my federal situation.
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Kaitlyn Otto
I'm in almost the exact same boat - 26, never filed, W-2 employee, and absolutely terrified. Reading through all these responses has been incredibly helpful and reassuring. It sounds like the key steps are: 1) Get wage transcripts from the IRS website, 2) Check if they've filed substitute returns for me yet, 3) File the back returns myself (prioritizing recent years for potential refunds), and 4) request first-time penalty abatement if needed. The fact that so many people here were owed refunds instead of owing money gives me hope. I've been losing sleep over this for months thinking I'd owe tens of thousands, but it sounds like having taxes withheld from paychecks usually works in our favor. Thank you everyone for sharing your experiences - it's made this feel way less scary and more manageable.
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Carmen Ortiz
•You've summarized the key steps perfectly! I just wanted to add one more piece of encouragement - I was in a similar situation at 29 (hadn't filed for 5 years) and kept putting it off because of the fear. The anticipation and anxiety was honestly worse than actually dealing with it. One tip that helped me get started: I tackled just ONE year first instead of trying to do everything at once. Pick your most recent year, get that transcript, and see what happens. For me, seeing that first refund check come in the mail was such a relief and gave me momentum to handle the rest. You don't have to solve everything overnight - just start with one year and build from there. You're already ahead of where I was because you're asking the right questions and have a plan. The hardest part is behind you!
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Mateo Perez
This thread has been incredibly helpful for someone like me who's been putting off dealing with unfiled taxes. I'm 31 and have been avoiding this for years due to pure anxiety and not knowing where to start. One thing I'd add from my research is that the IRS has an online payment agreement tool if you do end up owing money. You can set up a payment plan directly on their website without having to call (which we all know can be a nightmare). The monthly payment amounts are usually very reasonable based on your income and expenses. Also, for anyone worried about the complexity - TurboTax and other software can handle prior year returns, not just current year. I was surprised to learn you can e-file returns going back several years, which makes the process much faster than mailing paper returns. The biggest takeaway for me from reading everyone's experiences is that the IRS really isn't the scary monster I built up in my head. They genuinely seem to work with people who come forward voluntarily and make an effort to get compliant. Reading about all the people who ended up with refunds instead of owing money has finally given me the courage to tackle this myself.
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Mateo Rodriguez
•Thanks for mentioning the online payment agreement tool - I had no idea that existed! That takes away another layer of stress about having to deal with phone calls if I do end up owing money. The point about being able to e-file prior year returns is huge too. I was dreading the thought of printing, mailing, and waiting months for paper processing. Knowing I can handle most of this electronically makes it feel so much more manageable. It's really encouraging to see how many people in this thread went from terrified to successfully resolved. I keep coming back to read these responses whenever my anxiety spikes about tackling this. Sometimes you need to hear from real people who've been through the exact same situation to realize it's not as catastrophic as your brain makes it out to be.
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Jamal Wilson
As someone who just went through this exact situation last year, I want to echo what everyone else has said - you're making the right choice by addressing this now, and it's likely not as bad as you think. I was 30 when I finally dealt with 6 years of unfiled returns. Like you, I was a W-2 employee with taxes withheld, and I ended up getting refunds for 4 out of those 6 years! The two years I owed money on had very manageable amounts, and the IRS accepted my first-time penalty abatement request without any pushback. One practical tip that really helped me: start by calling the IRS Practitioner Priority Line at 866-860-4259 if you're working with a tax professional, or use the regular taxpayer line. They can tell you upfront if they've already filed substitute returns for you, which changes your strategy completely. The whole process took me about 3 months from start to finish, and the relief I felt afterward was incredible. I wish I hadn't let fear keep me paralyzed for so long. You've got this - just take it one step at a time!
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Demi Lagos
•This is exactly what I needed to hear! The fact that you got refunds for 4 out of 6 years is so encouraging. I've been putting this off for way too long because I convinced myself I'd owe some massive amount that would ruin me financially. Can I ask - when you requested the first-time penalty abatement, did you need to provide a detailed explanation or was it pretty straightforward? I'm wondering if I should have my "reasons" for not filing all prepared in advance or if they don't really dig into the why too much when it's your first time asking for abatement. Also, did you end up using a tax professional or handle it yourself? I keep going back and forth on whether the peace of mind is worth the extra cost, especially after reading about all these helpful tools people have mentioned. Thanks for sharing your timeline too - knowing it took about 3 months helps me set realistic expectations instead of thinking this needs to be solved overnight.
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