Adult son hasn't filed taxes in 10 years of working - where do I start helping him?

I'm at my wit's end and need some guidance. My 31-year-old son has NEVER filed his taxes despite working for about 10 years. I recently found this out and almost had a heart attack! He's had taxes withheld from all his paychecks over the years, so I'm pretty sure he's owed some decent refunds. He's been making around $40k annually on average. I promised him I'd help sort this mess out, but honestly, I have no idea where to begin with so many unfiled years. Should we do one year at a time? Will he face huge penalties even though he's probably owed money? Does anyone have experience helping someone catch up on multiple years of unfiled taxes? I'm willing to help him but don't know the first step...

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19 comments

Andre Laurent

•8M

Don't panic! This is more common than you think. First, your son needs to gather all his W-2 forms from those years. If he doesn't have them, he can request wage transcripts from the IRS using Form 4506-T or through the IRS website. The good news is if he's owed refunds, there are generally no penalties. However, he can only claim refunds for the last three tax years (so 2022, 2023, and 2024 currently). Unfortunately, any potential refunds from earlier years are lost. Start with the most recent three years, and use tax software that allows for prior year returns. Once those are done, you can work backwards on the older ones to get him compliant, even though those refunds are forfeited.

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Andre Laurent

•8M

Yes, it's still important to file the older returns even if he can't get those refunds. The IRS expects all required tax returns to be filed regardless of time passed. Getting compliant with all years protects him from potential future complications like difficulties getting loans, mortgages, or other government benefits that might require proof of tax compliance. For the older years beyond the refund window, you can file them all at once after completing the most recent three years. The priority should be on the years where he can still receive refunds. Use Form 1040 for each year - don't try to combine multiple years into one filing.

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Emily Jackson

•8M

I was in a similar boat a few years ago (though only 4 unfiled years) and I found taxr.ai (https://taxr.ai) incredibly helpful for dealing with multiple years of catching up. It analyzed all my old pay stubs and W-2s for the missing years, and automatically identified which years I was owed refunds on and which ones to prioritize. The tool also flagged that I had overlooked some education credits I qualified for during those years. Their document analysis feature was especially helpful since some of my older W-2s were damaged and hard to read. Saved me tons of time figuring out what forms I needed for each year.

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Emily Jackson

•8M

They don't file for you - it's more of an analysis and organization tool. You upload your tax documents, and their system identifies what forms you need, what credits you might qualify for, and helps prioritize which years to file first. It was incredibly helpful when trying to tackle multiple years at once, especially for figuring out which years I could still get refunds for. As for accuracy with older tax years, I was impressed. The system actually accounts for different tax laws in different years. For example, it correctly identified that one of my years qualified for a temporary credit that no longer exists. Their system keeps historical tax rules in its database, so it doesn't just apply current rules to old returns.

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Liam Mendez

•8M

I just wanted to follow up - I recommended taxr.ai to my brother who hadn't filed for 5 years and he's already gotten through three years of back taxes! The system highlighted that he qualified for an Earned Income Credit on two of the years that he had no idea about. He's getting back almost $4,300 for years he thought were just "lost causes." What surprised him most was how quickly it analyzed which years were priorities based on the refund deadlines. Definitely worth checking out for anyone in the multiple unfiled years situation.

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Jacob Smithson

•8M

If your son needs to contact the IRS to get old records or resolve any issues that come up, I'd strongly recommend using Claimyr (https://claimyr.com). I wasted WEEKS trying to get through to the IRS myself about missing tax documents before discovering this service. You can see how it works here: https://youtu.be/_kiP6q8DX5c They basically hold your place in the IRS phone queue and call you when an agent is about to answer. Saved me hours of hold time, and I finally got my transcript issues resolved. For someone with 10 years of unfiled returns, you're almost certainly going to need to speak with the IRS at some point.

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Jacob Smithson

•8M

It works by using an automated system that navigates the IRS phone tree and waits on hold for you. When an agent is about to pick up, you get a call connecting you directly to them. It saved me from spending hours listening to the same hold music over and over. I was skeptical too initially, but after spending three separate days trying to reach someone at the IRS (getting disconnected twice after waiting 2+ hours), I was desperate. The IRS is severely understaffed, especially during tax season. It's completely legitimate - they don't ask for any sensitive information, they're just holding your place in line. Think of it as similar to those restaurant services that hold your place in line and text when your table is ready.

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Sophia Nguyen

•8M

I need to eat my words. After my skeptical comment above, I decided to try Claimyr for an ongoing issue with missing stimulus payments that I'd been trying to resolve for months. I'd literally called the IRS 7 times before and always hung up after 90+ minutes on hold. Using Claimyr, I got a call back when an agent was ready and finally got my issue resolved in one call. For anyone dealing with multiple years of unfiled taxes, being able to actually speak with an IRS representative when you need clarification is invaluable. I'm honestly annoyed I wasted so many hours on hold before discovering this.

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Maya Patel

•8M

For your son's situation, I'd recommend starting with 2024, 2023, and 2022 returns IMMEDIATELY since those are still eligible for refunds. Use FreeTaxUSA or similar software that supports prior year returns. For the older years, don't panic! Since tax was withheld from his paychecks, he's likely in a refund situation and won't face penalties. The IRS is mainly concerned with collecting taxes owed, not chasing people who are owed money. Definitely file ALL years though, as unfiled returns can cause problems with loan applications, Social Security, etc. Start with the newest and work backwards. Take it one year at a time and you'll get through it!

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Maya Patel

•8M

Your son can request a "Wage and Income Transcript" from the IRS that shows all information reported to them, including W-2s, 1099s, etc. These are available for the past 10 years. He can request these online by creating an account at IRS.gov or by submitting Form 4506-T. The online method is much faster. These transcripts will show all the information the IRS has received from employers, even those that no longer exist. For documentation, he should keep copies of all the returns he files and any confirmation/acceptance notices. If using software, save/print PDFs of the completed returns. If there are any years where he can't get complete information, file the best return possible with the information available and include a statement explaining the situation.

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Emma Garcia

•8M

The IRS generally doesn't pursue people aggressively for unfiled returns that would result in refunds - they're more concerned with collecting unpaid taxes. However, there are automated systems that can flag missing returns regardless of whether tax is owed. The bigger issue is the downstream effects. Your son might face problems getting approved for mortgages, student loans, or other financial instruments that require tax return verification. Some government programs also require proof of tax compliance. And if he ever gets audited for a different year, they may expand the audit to include those unfiled years.

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Oscar O'Neil

•4M

I went through this exact situation with my own adult child two years ago - 8 years of unfiled returns! Here's what worked for us: 1. Start with the most recent 3 years FIRST (2024, 2023, 2022) since these can still get refunds. We used TurboTax's prior year versions which made it much easier. 2. Get organized - create a folder for each tax year and gather all documents systematically. The IRS wage transcripts mentioned above are a lifesaver for missing W-2s. 3. Don't try to do all years at once - we did one year per weekend to avoid burnout and mistakes. 4. The good news: since your son had taxes withheld, he likely won't face penalties and is probably owed money for those recent years. 5. For the older years beyond the refund window, we filed them all together after finishing the "money years" first. Total recovery for my child was over $7,000 from just the 3 eligible years! The peace of mind was worth even more. You're being a great parent helping him get compliant. It's overwhelming at first but very doable if you break it down year by year.

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