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Need help after not filing taxes for about 20 years - where do I even start?

I haven't filed taxes in about 20 years and I'm finally ready to face this mess. For the first decade, I was self-employed and really struggling with some personal issues. During those years, I made decent money (around $105,000 in my best year) but didn't pay anything in taxes. I had one dependent child during that time. The more recent decade has been less concerning - I've been employed with regular payroll deductions taken out, but still haven't actually filed returns. My child was still my dependent for the initial years of this period. I've had only single withholding taken from my paychecks. I know the IRS was looking for me during those early years because they sent notices to my old address. They even filed a substitute return on my behalf for at least one year. I want to finally fix this situation, but I have no idea where to begin. Because of depression and mental health struggles during those first 10 years, my recordkeeping was terrible. The companies I did independent contractor work for have gone out of business, and honestly, I don't even remember all their names. I might have some 1099s somewhere, definitely not all of them. Almost all documentation for my business expenses is gone - stored on old computers I no longer have. I only have about $5,000 in savings, so hiring a professional seems out of reach even though I know that would be the best approach. Can anyone suggest next steps? If the IRS only keeps records for 10 years, how do I handle those first 10 years with my terrible records? Should I start by calling the IRS directly and explaining I want to make things right? Or should I focus on filing for the more recent 10 years first?

Friendly reminder that even if some tax debts are beyond the collection statute of limitations, unfiled tax returns still need to be addressed if the IRS requests them. The 10-year limit is for collecting assessed taxes, not for requiring returns to be filed. Also, if you ever filed for bankruptcy, applied for a mortgage, or had other major financial events, those can sometimes extend or "toll" the collection statute.

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This is super important! My cousin thought he was in the clear after 10 years but the IRS still came after him because he had a period where he lived overseas which "paused" the statute clock. Definitely worth checking if anything in your history might have extended the statute.

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GalaxyGlider

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I really feel for you - 20 years is a long time to carry this burden, and it takes real courage to finally tackle it. The mental health struggles you mentioned are more common than you think in these situations. Here's what I'd suggest as your immediate next steps: 1. **Get your tax transcripts first** - File Form 4506-T or request them online at irs.gov. This will show you exactly what the IRS has on file for each year, including any substitute returns they filed. 2. **Start with the most recent 6 years** - This aligns with IRS voluntary disclosure practices and gets you current faster. Since you had regular withholding during this period, some years might actually result in refunds. 3. **Don't panic about perfect records** - For those early self-employment years with missing documentation, you can make reasonable estimates based on what you remember. Bank deposits, credit card statements, even old calendars can help reconstruct income and expenses. 4. **Consider the Volunteer Income Tax Assistance (VITA) program** - They offer free tax help for people with limited resources. Given your situation and savings constraints, you might qualify for their services. The fact that you're reaching out shows you're ready to handle this. Take it one year at a time, and remember that the IRS generally wants to work with people who are making a good faith effort to get compliant.

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This is really helpful advice, especially about the VITA program - I had no idea that existed! One question about reconstructing those early self-employment years: if I can only remember rough income amounts but have almost no expense documentation, is it better to file with just the income and no deductions, or try to estimate reasonable business expenses? I'm worried about looking like I'm making things up, but I also know I had legitimate business costs that I just can't prove anymore.

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Maya Lewis

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Something nobody has mentioned yet - make sure you're actually subject to US taxation in the first place. If you're truly just selling e-books through Amazon KDP (or similar platform), you might be receiving royalty income, not freelance/contractor income. Different types of income are treated differently under US tax law. For royalty income from intellectual property, you might have different options than for services income. This distinction could affect both your ITIN application purpose and your ultimate tax liability.

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This is a really good point! I didn't specify clearly in my post. I'm doing graphic design work directly for US companies, so I'm pretty sure that counts as service income/contractor work. But I'm curious - how would royalty income be treated differently? Would the withholding requirements be any different?

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Maya Lewis

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For service income as an independent contractor, you're generally subject to the 30% withholding without a tax treaty, exactly as you've experienced. Getting an ITIN allows you to file a tax return and potentially claim deductions, but the initial withholding typically still applies. Royalty income (like from book sales, licensing intellectual property, etc.) is technically also subject to 30% withholding without a treaty. However, the key difference is how these can be reported. With royalty income, you might qualify for certain expense deductions or business structures that aren't available for pure service income. Additionally, some digital platforms have special arrangements with the IRS regarding how they handle international sellers, so the practical implementation sometimes varies. For your graphic design work, you're definitely dealing with service income, so focusing on the ITIN application is the right approach. Just make sure when you complete your W-8BEN form after getting your ITIN that you correctly classify your income type.

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I went through this exact process about 6 months ago as a freelance web developer from the Philippines (also no tax treaty). A few practical tips that really helped me: First, when gathering your identity documents for the ITIN application, make sure your passport is valid for at least 6 months beyond your application date. The IRS rejected my first application because my passport was expiring in 4 months. Second, consider timing your application carefully. I applied in August (non-tax season) and got my ITIN in about 6 weeks. Friends who applied during tax season waited 12+ weeks. Third, once you get your ITIN, you'll need to be proactive with your US clients about updating their records. Send them the completed W-8BEN form via certified mail or email with read receipts. Some companies have slow accounting departments and it took 2-3 months for the withholding changes to take effect. One thing that surprised me - even after getting my ITIN and filing my first US tax return, I only got back about 15% of what was withheld (not the full 30%). The actual tax rate on my income bracket was still around 15%, but I was able to claim some business deductions for my home office and equipment. Still a significant improvement from losing the full 30% though!

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StarSeeker

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This is incredibly helpful, thank you! The passport validity tip is something I wouldn't have thought of - mine expires in about 8 months so I should be okay there. Quick question about the business deductions you mentioned - what kind of equipment and home office expenses were you able to claim? I have a pretty substantial setup with professional design software, monitors, and a dedicated workspace, but I wasn't sure if those would qualify for someone working internationally for US companies.

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Quick tip: If you're using TurboTax or H&R Block software, when you enter your 1098 information, they'll specifically ask about property taxes paid. Enter what's in Box 10 BUT ALSO have your actual property tax statements handy. The software will help reconcile any differences. I found out that my mortgage company only paid a portion of my property taxes from escrow, and I paid the rest directly to the county. If I had only claimed what was on my 1098, I would have missed out on about $2,300 in additional deductions for the portion I paid directly.

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This is such a helpful thread! I had the exact same confusion with my 1098 form last year. One thing I'd add is that if you have multiple properties or a complex escrow situation, it's worth requesting a detailed breakdown from your mortgage servicer. I called my lender and asked for an escrow analysis statement that showed exactly when each property tax payment was made and for which tax period. This helped me figure out that some of my 2023 tax year payments were actually made in early 2024, so they wouldn't appear on my 2023 1098 form. The bottom line is: always use your official county property tax statements as the source of truth, and treat the 1098 as helpful supplementary information. The asterisk is just their way of saying "we're giving you this info to help, but don't hold us responsible if there are discrepancies.

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Ava Garcia

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If you're in California, don't forget to file your state taxes too! They go to a completely different address: Franchise Tax Board PO Box 942840 Sacramento, CA 94240-0001 I made that mistake once thinking they were somehow connected.

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Andre Dupont

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Thank you for the reminder! I actually already sent my state return last week, but this is good info for anyone else in my situation. California's FTB website was surprisingly much clearer than the IRS about where to send everything.

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Harold Oh

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The confusion about mailing addresses is totally understandable - the IRS has been consolidating processing centers and the information online isn't always updated consistently. For California residents filing prior year returns without payment, the current address should be: Department of the Treasury Internal Revenue Service Ogden, UT 84201-0002 However, this can vary depending on the specific tax year you're filing for. For returns older than 2019, you might need to use the Austin, TX center instead. My advice: Before you mail anything, try calling the IRS at 1-800-829-1040 to confirm the correct address for your specific situation and tax year. Yes, the wait times are brutal, but it's worth the peace of mind to know you're sending it to the right place. Make sure to send it certified mail with return receipt so you have proof of delivery. Also, definitely include a cover letter clearly stating which tax year you're filing for and write the tax year prominently on your Form 1040. This helps prevent processing delays.

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Yuki Ito

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This is really helpful, thank you! I've been going in circles trying to figure this out. One quick question - when you say "returns older than 2019" go to Austin, does that mean 2018 and earlier, or does 2019 itself go to Austin? I'm filing for 2019 specifically and want to make sure I get the right address. Also, any tips for getting through to that IRS phone number faster? I've tried calling a few times but the wait times are crazy long.

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Emily Sanjay

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Random question but related - does anyone know if unemployment benefits count toward the income that's measured against the standard deduction? I got laid off for a few months last year and wondering how that affects all this.

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Yes, unemployment benefits are considered taxable income by the IRS, so they do count toward your total income that's measured against the standard deduction. Many people don't realize this and get surprised when filing taxes! One thing to watch out for - sometimes unemployment doesn't withhold enough federal tax (or any at all if you didn't opt in), so you might end up owing money even if your total income is just slightly above the standard deduction. And like others have said, you'll still pay SS and Medicare taxes regardless.

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Just want to add one more important point that might help you plan for next year - if you're going to be in a similar income situation, you might want to consider adjusting your withholdings so you don't have as much federal income tax taken out of each paycheck. Since you'll only owe federal income tax on about $50 of your income, you're probably having way more federal tax withheld than necessary. You could use Form W-4 to reduce your withholdings and get more money in each paycheck instead of waiting for a big refund. Just remember that SS and Medicare taxes (7.65% total) will always be taken out regardless. This way you'd have more cash flow throughout the year instead of essentially giving the government an interest-free loan. Just make sure to set aside a small amount for that ~$50 in federal tax you'll actually owe!

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This is really smart advice! I never thought about adjusting withholdings when you're barely above the standard deduction. @Noah Ali this could be perfect for your situation - instead of waiting for a big refund, you could have that extra money in your paychecks throughout the year. Just make sure you understand how to fill out the W-4 correctly so you don t'end up owing money at tax time. The IRS has a withholding calculator on their website that can help you figure out the right amount.

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