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.

This entire discussion has been absolutely phenomenal - what an incredible resource! As someone who's been lurking in this community for a while, I'm amazed by the depth of analysis and real-world experience everyone has shared. Reading through all these perspectives really highlights how marriage affects so many interconnected financial areas beyond just basic tax brackets. The systematic approach that's emerged here - using tax software for scenario modeling, the studentaid.gov calculator for loan projections, factoring in HSA limits, retirement account eligibility, employer benefits, and even mortgage qualification timing - seems like the gold standard for making this decision. What strikes me most is how the "right" answer really depends on your specific priorities and timeline. For some couples, minimizing student loan payments for another year might be worth more than the immediate tax benefits. For others, getting the mortgage documentation in place or maximizing long-term retirement account access might tip the scales toward an earlier wedding. The fact that @c6da548b9fab is thinking this through so thoroughly before the wedding puts them in such a strong position. Most couples don't discover these implications until they're already filing their first married tax return! One small addition: if you do end up with the December 2025 wedding timing for tax purposes, just make sure your venue and vendors can accommodate that date change if needed. The financial benefits are great, but logistics matter too! Thanks to everyone who shared such detailed experiences - this thread should be required reading for any couple planning marriage with similar financial considerations.

This thread has been absolutely incredible to read through! As a tax professional who's helped many couples navigate this exact decision, I'm impressed by the thoroughness of analysis everyone has shared. For your specific situation with similar incomes ($72k and $68.5k), you're likely looking at a modest marriage bonus rather than penalty - probably $500-1,200 in tax savings annually. The key factors working in your favor are the larger standard deduction and slightly lower effective tax rates when your incomes are combined. However, the student loan consideration is crucial. With $45k in loans on SAVE, your fiancé's payment could easily jump from ~$200-300/month to $500-700/month based on your combined income. That's $3,600-4,800 extra annually, which could outweigh the tax benefits in the short term. Here's what I'd recommend: Use the studentaid.gov calculator with your combined income to get the exact payment increase, then run your 2024 numbers through tax software both as singles and married filing jointly. This will give you real numbers instead of estimates. Also consider the long-term factors others mentioned - higher Roth IRA limits, better mortgage qualification, HSA contribution increases if you switch to family coverage, and future home sale exclusions. These often tip the scales toward earlier marriage timing even if there's a short-term student loan payment increase. The systematic approach this community has outlined is exactly what I use with clients - you're getting great advice here!

What an incredibly thorough discussion! As someone just starting to navigate these decisions with my college-bound senior, I'm realizing there are so many interconnected factors I hadn't even considered. One thing I'm curious about that hasn't been mentioned yet - what happens with state residency requirements for in-state tuition? My son will likely qualify for independent filing based on the support test, but I'm wondering if there are any state-specific rules that could affect his in-state tuition status if he files independently rather than as our dependent. Also, I've seen several mentions of keeping detailed expense records for the support test calculation. For those who have been through IRS audits or questions about this, what level of detail is actually required? Are we talking about keeping every receipt for textbooks and meals, or is it more about the major expense categories like tuition, housing, and general living costs? The health insurance angle that Omar brought up is definitely something I need to check with our HR department - I never would have thought that tax filing status could affect health coverage eligibility. These kinds of hidden connections between different financial decisions really highlight why this topic is so complex! Thanks to everyone for sharing such detailed experiences and insights. This thread should be required reading for any parent with college-age kids!

This entire discussion has been absolutely invaluable! As a newcomer to these college tax decisions, I had no idea there were so many interconnected factors to consider beyond just "who gets the bigger refund." A few key takeaways that really stand out to me: 1. **Health insurance verification is critical** - I never would have thought to check with HR about dependent coverage requirements before making tax filing decisions. That could be a very expensive oversight! 2. **The support test documentation needs to be thorough** - It sounds like keeping detailed records of major expenses (tuition, housing, scholarships) throughout the year is essential, not just at tax time. 3. **This isn't just a one-year decision** - Understanding how independent filing might affect future financial aid, work-study eligibility, and establishing patterns for remaining college years is crucial. 4. **State-specific benefits matter** - From additional education credits to 529 plan contribution deductions, there are state-level implications that could easily be missed. One question I still have: For families right on the edge of the support test (maybe 48-52% range), are there legitimate strategies to help push a student over the 50% threshold? For example, if my daughter could delay some personal expenses until December or accelerate certain education-related payments, would that be appropriate for meeting the support test requirements? The tools and services mentioned here (taxr.ai, Claimyr) sound helpful for getting professional guidance, but I appreciate the advice about having a CPA verify the results for such an important decision. Thank you all for sharing your real-world experiences - this is exactly the kind of practical insight you can't find in IRS publications!