Been dealing with the IRS for 15+ years as a tax preparer. This years 810 freezes are taking way longer than usual to clear. The new AI verification system they implemented is causing major backlogs. Your best bet is to keep checking your transcript weekly for changes. If you want a detailed analysis of your situation, use taxr.ai - it's been a game changer for understanding these delays and predicting resolution timeframes. The system can analyze patterns across thousands of cases to give you a pretty accurate timeline. I've been recommending it to all my clients stuck in verification.

Ugh, I feel you on this! I've been stuck with an 810 freeze since April and it's driving me absolutely insane. The daily transcript checking has become like a bad habit at this point. What's really frustrating is how the IRS phone system just hangs up on you after waiting hours. I tried that taxr.ai thing that people mentioned and honestly it was pretty helpful - gave me some peace of mind knowing what's actually happening with my case instead of just staring at cryptic codes. At least now I have a better idea of when this nightmare might end. Stay strong! 💪

One thing I wanted to add that might help with your planning - you mentioned assuming the stock will be at $119 when you sell in July 2025. Just remember that with ESPPs, you're essentially making two decisions: the tax optimization decision (qualifying vs disqualifying) and the investment decision (when to sell based on market conditions). I've found it helpful to set up price alerts on my ESPP shares so I can monitor if there are any major price movements that might influence my selling decision. Sometimes the tax savings from waiting for a qualifying disposition can be completely wiped out by a market downturn, so it's worth keeping an eye on the stock performance as you approach your decision dates. Also, since you're getting that supplemental statement from your benefits team, make sure to save a digital copy in addition to the physical one. I learned this the hard way when I needed to reference an old ESPP transaction for an amended return and couldn't find the paperwork anywhere!

Great question about ESPP taxation! I've been through this exact scenario with my company's plan. One additional consideration I'd mention is to check if your company provides any ESPP tax modeling tools or has partnerships with financial planning services. My employer actually offers free sessions with financial advisors who specialize in equity compensation during open enrollment periods. They walked me through scenarios comparing immediate sale vs waiting for qualifying disposition, factoring in both tax implications and market risk. It was incredibly helpful for making an informed decision. Also, regarding the W-2 reporting - make sure to ask your benefits team exactly when the compensation income will appear. Some companies report it in the year of purchase (even for qualifying dispositions), while others report it in the year of sale. This timing can affect which tax year you need to plan for, especially if you're close to year-end when making your selling decision. The peace of mind from having official guidance from both your company and the IRS (as others mentioned) is definitely worth the effort when you're dealing with thousands of dollars in potential tax implications!

Don't forget that worthless securities are still subject to the capital loss limitations. You can only offset up to $3,000 of ordinary income per year after you've used the losses to offset any capital gains. Had to learn this the hard way when I tried to claim $12,000 in losses from some penny stocks that went to zero in 2022. I offset about $2,500 in gains from other stocks, then could only use $3,000 against my regular income. The remaining $6,500 had to be carried forward to future tax years.

I went through this exact situation last year with some defunct crypto mining stocks that got delisted. Here's what worked for me: First, contact your broker's tax department (not regular customer service) and specifically request a "worthless securities letter" or "abandonment letter." Most major brokers have a standard process for this. If your broker won't cooperate, you can still claim the loss but need to document everything yourself. Save screenshots of your account showing the securities, any emails with your broker, and find public records of when the companies went bankrupt or were delisted. For the tax filing, you'll use Form 8949 and Schedule D. Mark the transaction with code "W" for worthless, use December 31st of the tax year as the "sale" date, $0 as the sale price, and your original cost basis as the loss amount. One important thing - make sure you're claiming these in the correct tax year. Securities become "worthless" when there's no reasonable hope of recovery, which is usually when the company files bankruptcy or is officially dissolved, not necessarily when they stop trading. Keep all your documentation for at least 7 years in case the IRS has questions. The key is being able to prove you actually owned the securities and that they truly became worthless during the tax year you're claiming.

This thread has been absolutely incredible - thank you to everyone who shared their experiences and strategies! I'm actually an enrolled agent who specializes in wage and hour tax issues, and this discussion covers pretty much every viable option available under current law. A couple of additional technical points that might help: **IRS Notice 2018-83** provides some guidance on how to handle these cross-year repayment situations. While it doesn't change the $3,000 threshold, it does clarify documentation requirements that could be helpful if you're ever audited. **Consider the timing of your 2024 tax filing** - if your employer might still issue a corrected W-2 for 2023, you may want to file an extension to give yourself more time to pursue that option. Once you file your 2024 return showing the full repayment with no deduction, it becomes harder to argue for the corrected W-2 approach. **State-specific research is crucial** - I've seen cases where state tax savings from wage repayment deductions offset 20-30% of the federal double-taxation impact. States like California, New York, and several others have provisions that might help. The employer accountability issue everyone's discussing is spot-on. I regularly advise clients to get any promises about tax handling in writing before agreeing to repayment plans. Most HR departments don't understand the tax implications of their own payroll errors, which is why they make promises they can't keep. This really should be a standard resource for anyone dealing with employer payroll mistakes across tax years!

This situation is absolutely maddening and unfortunately very common! I went through something almost identical last year - employer overpaid me about $2,200 in 2022, I repaid it throughout 2023, and despite promises that they'd "handle the tax adjustments," I ended up in the exact same double-taxation trap you're describing. The most frustrating part is how HR departments seem to routinely make these promises without understanding the actual tax implications. They either don't know about the $3,000 threshold rule or they're just kicking the can down the road hoping you won't follow up. Here's what I learned from my experience: Don't give up on getting your employer to issue a corrected W-2 for 2023. While they're not legally required to do this for cross-year repayments, some will do it as a courtesy if you escalate high enough and frame it as a fairness issue. I had to go three levels up from my initial HR contact, but eventually got someone who understood that their payroll error was costing me real money through no fault of my own. Also, definitely check your state taxes - many states didn't adopt all the TCJA provisions and still allow these repayments as deductions. I was able to save about $180 on my state return even though I got no federal relief. Document absolutely everything - dates, amounts, and especially any communications where they promised to adjust your taxable wages. Even if it doesn't help immediately, you'll want that paper trail if you decide to escalate further or if the miscellaneous deduction rules change after 2025. The whole system is incredibly unfair to employees who are just trying to do the right thing by repaying money that wasn't rightfully theirs. Hang in there and don't let them dismiss this as "just a tax issue" - it's the financial consequence of their mistake!

Just wanted to add something important that I learned the hard way - even if you're selling personal items at a loss, you still need to keep good records to prove that to the IRS if they ever ask. I got a letter from them last year questioning some of my eBay sales because they had records from PayPal but I couldn't document my original purchase prices. Now I take photos of receipts when I buy anything valuable, even personal stuff, and store them in a folder on my phone labeled "Tax Records." For older items where I don't have receipts, I research what similar items sold for during the time period I bought them and keep screenshots as documentation. It's a pain but way better than dealing with IRS correspondence! Also, don't forget that if you use part of your home for storing inventory or photographing items, you might be able to deduct a portion of your home expenses on Schedule C. Every little deduction helps when you're self-employed!

Great question and you're smart to ask early in the year! I went through this exact situation a couple years ago. Here are the key points: 1. **Yes, you must report the income** even without a 1099. The IRS requires all income to be reported regardless of forms received. 2. **Where to report it:** If this is occasional selling of personal items, you might not need Schedule C. If you sold personal collectibles for less than you originally paid, that's actually a personal loss (not deductible, but also not taxable income). However, if you made a profit or this is becoming a regular business activity, you'll need Schedule C. 3. **Documentation is key:** That spreadsheet you mentioned is perfect! Include the item, original cost (estimate if needed), selling price, and any fees paid to eBay/PayPal. 4. **Don't forget deductions:** eBay fees, PayPal fees, shipping costs you paid, and packaging materials are all deductible business expenses if you're filing Schedule C. The fact that you're asking now instead of scrambling at tax time shows you're on the right track. I'd recommend consulting with a tax professional if your total sales were significant or if you plan to continue selling regularly - the rules can get tricky when you're mixing personal item sales with potential business activity.