One important thing nobody's mentioned: if you've been filing extensions, the statute of limitations on assessment hasn't started running. The IRS generally has 3 years from the date you file a return to assess additional tax. Since you haven't filed, that clock hasn't started. But here's the good news - the IRS typically only looks back 6 years for unfiled returns unless they suspect fraud. If you voluntarily come forward and file your back returns before they contact you, you're in a much better position than if they find you first. Also, self-employed people often overestimate what they'll owe because they forget about all the legitimate business deductions they qualify for. A good tax pro might find you qualify for things like home office deduction, health insurance deduction, SEP IRA contributions, business mileage, etc.

I'm a tax professional and want to reassure you that your situation, while stressful, is more common than you think. The fact that you've been filing extensions each year actually shows the IRS that you haven't disappeared - you're still engaging with the system, which works in your favor. Regarding your passport concerns: Since you haven't received any formal notices and there's no assessed tax debt on record, your passport renewal will likely be processed normally. The State Department only gets involved when there's a certified seriously delinquent tax debt over $59,000, which requires formal assessment first. Here's my recommended action plan: 1. **Immediate steps**: Gather all income documents (1099s, bank statements, PayPal records) for the last 6 years. Don't worry about perfection - estimates based on bank deposits work initially. 2. **Find the right help**: Look for an Enrolled Agent or CPA who specializes in unfiled returns. Many offer free consultations and can give you a realistic estimate of what you'll owe. 3. **Start with recent years**: File the last 3-6 years first. The IRS is most concerned with recent compliance. 4. **Consider voluntary disclosure**: Coming forward voluntarily before the IRS contacts you puts you in the best possible position for penalty abatements and payment plans. You're not a bad person - you're someone who got overwhelmed by a complex system. The anxiety you're feeling is actually your conscience telling you to make this right, which is admirable. Take it one step at a time.

Just went through this exact situation last month! They absolutely will take the full $750 regardless of how small it seems. I owed $680 in back child support and was expecting a $2,100 refund. Got a letter from the Bureau of Fiscal Service about a week before my refund date explaining the offset. They took exactly $680 and I received the remaining $1,420 about 10 days later than my normal refund timing. The process is completely automated once your name hits their database - there's no human reviewing whether the amount is "worth it" or not. If you haven't received a Pre-Offset Notice yet, definitely update your address with both the IRS and your state child support agency because those notices are crucial for understanding your options.

The $750 will definitely be taken - there's no minimum threshold for child support offsets. I work in tax preparation and see this constantly during filing season. The Treasury Offset Program is completely automated, so once you're in their system, any refund gets intercepted regardless of the amount. What many people don't realize is that you should have received a Pre-Offset Notice around December or January explaining this would happen. If you didn't get one, check that your address is current with both the IRS and your state child support enforcement agency. The good news is if your refund is larger than $750, you'll get the difference back - it just takes an extra 2-3 weeks to process after the offset. The key thing to remember is that disputing the amount needs to be done through your state child support agency, not the IRS. The IRS is just the middleman collecting the money.

Another important consideration - make sure you understand the difference between a "rollover" and a "transfer" when dealing with your distribution. What you received is considered an "indirect rollover" (also called a 60-day rollover) because the check was made out to you personally. The 60-day clock starts ticking from when you received the distribution, not when you cash the check. And you only get ONE indirect rollover per 12-month period across all your IRAs, so if you've done any other rollovers recently, this could be an issue. If you're feeling overwhelmed by the timeline, consider calling your intended IRA provider ASAP. Many can help walk you through the process and some will even accept the deposit over the phone with overnight delivery of paperwork to beat the 60-day deadline. Don't wait until the last minute - financial institutions can sometimes take a few days to process these transactions properly.

Just want to add one more critical timing consideration that could save you some stress - if you're getting close to the 60-day deadline, make sure to document EVERYTHING. Keep records of when you received the distribution check, when you deposited it into your IRA, and get confirmation from your IRA provider that they've processed it as a rollover contribution. I've seen situations where people met the 60-day deadline but the IRA provider didn't code the transaction correctly, leading to unnecessary headaches with the IRS later. Most reputable providers will give you a confirmation letter stating the rollover was completed within the required timeframe - definitely ask for this! It's your proof that you followed the rules if any questions come up during tax season. Also, remember that weekends and holidays don't extend the 60-day deadline - it's calendar days, not business days. So if day 60 falls on a weekend, you need to complete the rollover by the Friday before. Better to get it done with a few days to spare than risk missing the deadline by a technicality.

I actually had issues with my EIP going to a closed bank account. If that happened to you, the bank would have rejected it and the IRS should have mailed you a paper check instead. Did you move during the pandemic? That could explain why you never got it.

The good news is that you're not alone in this situation! Many people missed their EIP payments due to various processing issues during the pandemic. Based on your income level ($27,500), you were definitely eligible for all three payments totaling $3,200. Here's what I'd recommend doing in order: 1. **Check your IRS online account first** - Log into IRS.gov and look at your tax transcripts to see if any EIP payments show as issued to you. This will tell you if the problem was on the IRS side (they never sent it) or delivery side (sent to wrong address/account). 2. **File amended returns ASAP** - You'll need to file Form 1040-X for 2020 (for the first two payments) and 2021 (for the third payment). The 2020 deadline is coming up fast in April 2024, so prioritize that one. 3. **If you discover payments were issued but never received** - You'll need to request payment traces instead of filing amendments. Don't beat yourself up about this - the whole EIP rollout was chaotic and lots of eligible people fell through the cracks. The important thing is you're addressing it now while you still can. Those tools others mentioned (taxr.ai for document analysis and Claimyr for IRS phone support) could definitely help speed up the process if you get stuck.

Just a warning - our company tried to avoid reporting gym memberships as taxable and got audited. The IRS specifically looked at our wellness benefits and we ended up having to amend W-2s, pay back taxes, plus penalties. Not worth the risk in my opinion.

Thanks for sharing all these perspectives! As someone who's been dealing with payroll compliance for years, I want to emphasize that proper W-2 reporting really is the safest approach here. Nick, for your $65/month benefit, you're looking at adding about $780 annually to each employee's taxable income. While that might seem like a lot, many employees still find significant value in employer-sponsored gym benefits even when taxable - especially if you can negotiate group rates that are better than what they'd pay individually. One approach I've seen work well is being completely transparent about the tax implications upfront, but also highlighting the total value they're receiving. For example, if you can get gym memberships that would normally cost $80/month for $65 through group purchasing power, employees are still getting a $15/month discount even after paying taxes on the benefit. The key is clear communication - don't let it be a surprise on their first W-2. Include the tax impact in your initial rollout materials so employees can make informed decisions about participation.