This is a really frustrating situation, but you're definitely not alone in dealing with this backup withholding issue. I went through something similar with TD Ameritrade a couple years ago when they suddenly started enforcing the W-9 certification requirements more strictly. The key thing to understand is that this 24% backup withholding is essentially the IRS holding your money as collateral until you can prove you've properly reported your income. It's not a penalty - it's more like an overpayment that you'll get back when you file your taxes. Here's what I'd recommend based on my experience: 1. **Fix the W-9 immediately** - Log into your Robinhood account and complete the tax certification process. This won't get your current money back, but it will prevent future withholding. 2. **Keep detailed records** - Screenshot everything showing the withholding amounts, save all emails from Robinhood about this, and keep copies of your W-9 submission. 3. **Wait for your 1099-B** - Robinhood will send you a 1099-B form early next year that shows both your trading activity and the backup withholding amount. This is what you'll use to claim the credit on your tax return. 4. **File your taxes promptly** - The sooner you file, the sooner you can get your refund if you're owed one. The reason different brokers handle this differently is that they have varying levels of automation and verification systems. Some are more proactive about getting your tax info certified upfront, while others (like Robinhood apparently) are more reactive and impose withholding when issues arise. I know it's frustrating to have that money tied up, but at least it's earning you a guaranteed credit on your taxes rather than sitting in a low-interest account somewhere.

I went through this exact same situation with Robinhood last year and it's incredibly frustrating! The backup withholding caught me completely off guard too since I'd never had issues with other brokers. What helped me was understanding that this is actually a pretty common issue when transferring between brokers. Each brokerage has their own system for verifying tax information, and sometimes things don't transfer over properly even if you had everything set up correctly at your previous broker. A few things that might help: **Immediate steps**: Log into your Robinhood account right now and look for their tax documents section. You'll need to complete a new W-9 form with them. Don't assume they have your info just because Schwab did - treat it like a completely fresh setup. **Documentation**: Take screenshots of everything showing the backup withholding amounts and save all communications about this issue. You'll want this paper trail when tax season comes. **Timeline expectations**: Unfortunately, there's no way around waiting until you file your 2025 taxes to get that money back. The IRS has already received it from Robinhood, so it's essentially an advance payment on your taxes. **Silver lining**: If you don't end up owing much in taxes, you'll likely get most or all of that $2k back as a refund. The backup withholding often ends up being more than people actually owe. The good news is that once you get the W-9 properly submitted and verified, this shouldn't happen again on future trades. Just make sure to confirm with Robinhood that they've processed it before making any more significant transactions. Hang in there - I know it's frustrating to have that money tied up, but you will get it back!

Great question about timing limitations! Generally, most counties allow property tax refund requests for 3-5 years back, but this varies significantly by jurisdiction. Some are more generous (up to 7 years) while others are stricter (only 2-3 years). You'll need to check your specific county's policy. For IRS amended returns, you typically have 3 years from the original filing date or 2 years from when you paid the tax, whichever is later. So there can definitely be timing mismatches where you might recover some years but not others. Here's the strategy I'd recommend: Start with the most recent tax years first since those are most likely to be within both the county refund period and the IRS amendment window. Work backwards from there. Even if you can't recover everything, getting the recent years corrected is better than nothing. Also, document your good faith effort to correct the situation - if you can show the IRS you're proactively fixing an honest mistake, they're often more lenient about penalty waivers, even if some of the corrections fall outside normal time limits.

This is such a frustrating situation, but you're definitely not alone - I see property tax mix-ups like this more often than you'd think, especially when autopay is involved. The good news is that this is absolutely fixable, though it will require some persistence. One thing I haven't seen mentioned yet is to check if your mortgage company was involved in the original closing. If you had an escrow account for taxes, they should have notified the county about the ownership change. If they failed to do this properly, they might bear some responsibility for the ongoing payments and could help expedite the correction process. Also, when you contact the county offices, ask specifically about their "erroneous payment refund process" - most counties have a formal procedure for exactly this situation. Don't just explain the problem; ask for their standard form for property tax refunds due to ownership errors. This often moves things along faster than trying to explain the whole situation from scratch each time. The tax implications are definitely something to address proactively. Since you've been claiming deductions you weren't entitled to, filing amended returns voluntarily (before the IRS discovers the issue) usually results in much more favorable treatment. You'll likely face interest on any additional taxes owed, but penalties are often waived for voluntary corrections of honest mistakes. One last tip - if you run into bureaucratic roadblocks, ask to speak with a supervisor or property tax specialist rather than general customer service. They're usually much more familiar with resolving these types of ownership transfer issues.

Check if you might qualify for the IRS Fresh Start program too. It helps people who owe back taxes with payment plans and might even reduce penalties. I owed about $3k from 2016 and was able to set up a monthly payment plan of just $85. The most important thing is to be proactive and contact them before they start more aggressive collection actions.

I went through something very similar with a 2016 tax debt that I discovered years later. That transcript format can be really confusing at first! The key thing to understand is that your original debt was $2,750.35, but it's now grown to over $3,700 with interest and penalties. Here's what I'd recommend based on my experience: First, call the IRS to get your current balance since that transcript is from 2022 and more interest has accumulated. Second, ask about penalty abatement options - you might qualify for first-time penalty abatement if you had clean tax history before 2017. Third, don't panic about paying it all at once - the IRS offers payment plans even for older debts. The most important thing is to address this proactively. I waited too long and ended up with a tax lien that took months to resolve. But once I called and set up a payment plan, the stress went away and I was able to handle it with manageable monthly payments. You've got options, so don't let the anxiety overwhelm you!

I've been following this thread closely as I'm in a similar situation with employer-paid disability premiums. One thing I wanted to add that might help others - if you're still unsure about your specific situation after reviewing your plan documents, you can also request a written clarification from your benefits administrator or payroll department. I did this last year when I couldn't determine from my paystub whether the premiums were being treated as taxable income. I sent a simple email asking: "Are the disability insurance premiums paid by the company included in my taxable wages, and if so, in what amount?" They responded with the exact dollar amounts and confirmed the tax treatment. This documentation became really valuable when I was preparing my taxes, and it also helped me understand that I had the option to change my election during the next open enrollment period. Sometimes the most direct approach - just asking your employer's benefits team - can save a lot of confusion and research time. The key is asking for the information in writing so you have it for your tax records, rather than relying on a verbal explanation that you might misremember later.

As a newcomer to this discussion, I'm really grateful for all the detailed explanations here! I'm dealing with a similar situation where I just started a new job that offers disability insurance, and I had no idea there were different tax treatments depending on how the premiums are structured. One question I have after reading through all these responses - if my employer gives me the choice between having them pay the premiums (making future benefits taxable) versus having the premiums deducted from my after-tax pay (making future benefits tax-free), how do I decide which option is better? Is there a rule of thumb for evaluating whether it's better to pay tax on the smaller premium amount now versus potentially paying tax on larger benefit payments later if I ever become disabled? I imagine it depends on factors like my current tax bracket, expected future tax rates, and the likelihood of actually needing the benefits, but I'm not sure how to weigh all of that. This thread has already taught me so much about disability insurance taxation that I never knew before!

make sure u file those kids as dependents correctly tho. IRS be clownin people who mess that up 🤡

Just wanted to add - definitely file for the Child Tax Credit and Additional Child Tax Credit if you qualify! With 4 kids and that income level, you could be looking at up to $2,000 per child. Also, since you're doing gig work, make sure you're tracking business expenses like phone bills, car expenses, etc. for next year. The standard mileage deduction is usually the way to go for delivery drivers. Don't stress too much - sounds like you'll probably come out ahead with those credits!