I've been following this discussion as someone who went through a similar wash sale nightmare with Robinhood last year, and I wanted to add some practical insights that might help. The most important thing to understand about your $5,000 in disallowed wash sales is that these losses aren't lost forever - they're added to the cost basis of your replacement securities. However, to actually claim these deferred losses, you need to completely exit ALL positions in those underlying securities (both stock and options) and stay out for 30+ days. For your PYPL situation showing $0.00 profit/loss, this is almost certainly a display glitch in their system. I experienced the exact same issue where Robinhood's system couldn't properly calculate or display wash sale adjustments for complex options transactions. What likely happened is you sold PYPL options at a loss and then bought PYPL stock (or different PYPL options) within 30 days, triggering the wash sale rule. Here's what I recommend based on what actually worked for me: 1. **Create a comprehensive transaction timeline**: Download your complete CSV history and map out every single trade (not just the flagged ones) for each security showing wash sales. Look for ANY stock or options purchases within 30 days before or after your loss transactions. 2. **Use specific language with support**: Instead of general inquiries, say "I need to review incorrect wash sale calculations on my 1099-B with your tax reporting department." This usually routes you to someone who understands options taxation rather than script-reading general support. 3. **Consider strategic position exits**: If you want to recover the deferred losses this tax year, you'll need to sell all positions in those securities and avoid them for 30+ days. Weigh this against the value of holding those positions. 4. **Plan better for next year**: Use different but correlated securities during wash sale periods. For example, trade SPY options when you have QQQ losses, or use sector ETFs instead of individual stocks. The wash sale rules are particularly tricky with options because the IRS considers options and their underlying stock to be "substantially identical" securities. Even different strike prices and expiration dates can trigger wash sales if they're on the same underlying asset. Don't panic about the money being gone - it's just temporarily deferred until you make clean breaks from those positions. The key is understanding exactly what triggered each wash sale so you can avoid similar issues going forward.

I've been dealing with wash sale issues on options for a couple years now, and one thing that's helped me avoid this headache is keeping a simple "cooling off" calendar. Whenever I close an options position at a loss, I mark that ticker on my calendar and don't touch it (stock OR options) for 31 days minimum. It sounds basic, but after getting burned by wash sales my first year of active trading, I realized the tax complexity just isn't worth trying to optimize around. The peace of mind knowing I won't accidentally trigger wash sales has been huge. For your current situation with the $5,000 in disallowed losses - everyone's right that they're deferred, not lost. But here's something to consider: if those losses are spread across multiple securities, you might want to prioritize which positions to exit based on your actual investment thesis. Don't let the tax tail wag the investment dog. One more tip for dealing with Robinhood: if their tax department gives you the runaround, you can also request your complete transaction data and work with a tax professional to override their calculations on your return. Sometimes that's faster than fighting for a corrected 1099, especially this late in tax season.

Be careful with the advice about "selling at a loss isn't taxable." While that's generally true for personal items, if you're regularly selling stuff online, the IRS might consider you to be running a business, which has different rules. The frequency of sales, whether you're buying items to resell, and your intent all factor in.

Great question Sofia! The confusion is totally understandable since the rules have been changing. For 2024 tax year, the 1099-K threshold is $5,000 - the IRS postponed the planned reduction to $600. Since you're just clearing out personal items (clothes, electronics, collectibles), most of what you're selling probably won't be taxable income anyway. If you're selling items for less than what you originally paid, that's considered a personal loss and isn't reportable income. Only if you sell something for more than your original purchase price would you potentially have taxable capital gains. Keep basic records of your sales and what you originally paid for items (even rough estimates are okay for personal belongings). The 1099-K threshold is just about when platforms must send you a form - you're technically supposed to report all taxable income regardless, but again, most personal item sales at a loss aren't taxable anyway. Don't stress too much about it - sounds like you're just doing normal decluttering, not running a business!

Based on your income levels, you're right to think strategically about this. Here's what you need to know: You CANNOT file as Head of Household without claiming at least one qualifying dependent - that's a hard IRS requirement. So your idea of filing HOH while letting your partner claim both kids won't work. Your best option is likely for each of you to claim one child and both file as HOH. This gives you both the better tax brackets and higher standard deductions that come with HOH status. Even though you're over the income limit for child tax credits, the HOH filing status itself provides significant tax savings compared to filing Single. Your partner will get the full child tax credit and likely EITC for their claimed child, while you'll still benefit from the HOH tax brackets and standard deduction for yours. Just make sure you document who pays for what household expenses throughout the year. The IRS does scrutinize unmarried couples who both claim HOH, so keep records of rent/mortgage, utilities, groceries, and childcare costs to show you're both legitimately supporting the household. One more thing - definitely coordinate clearly about who claims which child before filing. I've seen too many people accidentally both claim the same kid, which triggers an automatic IRS review and major delays.

As a tax professional, I want to emphasize a few key points that haven't been fully addressed yet: First, you're absolutely correct that you cannot file as Head of Household without claiming at least one qualifying dependent. The IRS is very strict about this requirement. However, there's an important nuance about the "support test" that others haven't mentioned. For unmarried parents living together, each child can only be claimed by one parent, and that parent must provide more than half of the child's total support for the year. This includes housing, food, clothing, medical care, education, and other necessities. Given your income difference ($190k vs $32k), you're likely providing more than half the support for both children through housing costs, insurance, and general living expenses. This means you might actually be the only one who can legally claim either child as a dependent, even if your partner is the primary caregiver. I'd strongly recommend getting professional advice or using the IRS Interactive Tax Assistant tool to determine who actually qualifies to claim each child based on the support test. The "tiebreaker rules" only apply when both parents equally meet all the dependency tests. Also, keep in mind that even if splitting the dependents is allowed in your situation, you'll want rock-solid documentation of how expenses are divided, especially since both filing as HOH with your income levels will likely trigger IRS scrutiny.

Just a heads up - if you decide to estimate your income, be VERY careful about tips. The IRS watches server income closely because underreporting tips is common. Remember that Denny's would have reported your credit card tips, and they've likely already submitted that info to the IRS.

Dylan, I went through this exact situation a few years back with a restaurant job! Here's what worked for me: First, try to reconstruct your income using any records you have - bank deposits, credit card statements showing tip deposits, even text messages about your schedule. For the W-2 issue, you have two main paths: 1) File Form 4852 with your best estimates, or 2) Try to get your wage transcript from the IRS first (either online or by calling). The transcript will show exactly what Denny's reported. One thing to keep in mind - restaurants are required to report all credit card tips to the IRS, so they definitely have records of at least that portion of your income. Your estimate needs to be reasonably close to what they reported, especially for tips. If you're running out of time before the deadline, don't panic about filing an extension (Form 4868). It gives you until October 15th to file, though you still need to pay any taxes owed by the original deadline to avoid penalties. The key is don't skip reporting this income entirely - that will cause bigger problems than filing with reasonable estimates and correcting later if needed!

Welcome to the community! I'm in a very similar situation - started playing social casinos about 6 months ago and now trying to navigate this tax maze. This thread has been incredibly educational. One thing I wanted to add based on my recent experience: when requesting transaction records from customer service, also ask specifically about their "coin conversion rates" if your platform uses multiple types of virtual currency. My platform has gold coins, sweep coins, AND bonus coins, each with different redemption rules. Understanding these distinctions helped me realize that some of my "big wins" were actually just bonus coins that can't be cashed out. Also, for anyone using multiple social casino platforms (like I do), make sure you're tracking each one separately. The tax reporting requirements are the same, but each platform has different policies about record retention and customer service responsiveness. I learned this the hard way when one platform was super helpful with detailed records while another basically told me to figure it out myself. The advice about starting fresh with better record-keeping for 2025 resonates strongly. I've set up a simple system where I take a screenshot before and after each session, and immediately log the key details in a shared Google Sheet that my spouse can access too (in case something happens to me). It takes literally 2 minutes but will save hours of reconstruction work next tax season. Thanks everyone for sharing your real experiences - it's so much more helpful than the generic tax advice you find elsewhere!

As someone who just discovered this community while frantically googling "social casino tax help," I can't thank everyone enough for this incredibly detailed discussion! I'm in almost exactly the same boat as the original poster - got into social casinos about 8 months ago and now staring down tax season with about $3,200 in cashouts and roughly $800 in coin purchases. Reading through all these experiences has been both reassuring and eye-opening. I had no idea about the sweep coin vs. gold coin distinction for tax purposes, or that I could request detailed transaction histories from customer service. I literally thought I was going to have to piece everything together from my credit card statements alone. The consensus seems crystal clear: report the cashouts as "Other Income" and don't try to hide anything from the IRS. The advice about checking whether itemizing actually makes sense versus taking the standard deduction is huge - I was automatically assuming I should try to claim my losses without doing the math on total deductions. I'm definitely going to contact my platform's customer service this week to get those complete records before they potentially get purged. And starting that screenshot + spreadsheet system for 2025 is now at the top of my to-do list. For other newcomers stumbling across this thread - the practical advice here is worth its weight in gold. Thanks to everyone who shared their real experiences dealing with this relatively new tax situation. It's clear this community really looks out for each other!