I just wanna say it's crazy we even have to worry about this stuff. Like if I lose $10k one year and make $10k the next, I've made ZERO dollars over two years, but the tax system is set up to potentially tax me anyway. Seems designed to confuse regular people. Even if you can carry forward losses, you still have to know that's a thing and file the right forms.

This is exactly why I think it's worth investing in proper tax software or professional help when dealing with capital losses. The rules are actually pretty straightforward once you understand them, but the IRS doesn't exactly make it easy to figure out. For anyone reading this thread who's still confused: the key takeaway is that if you're married filing jointly, you can deduct up to $3,000 of capital losses against ordinary income each year, and carry forward the rest indefinitely with NO LIMIT on how much you can use to offset future capital gains. So in the original example, that $10,000 loss would fully offset the $10,000 gain the following year - no taxes owed on those gains. The person who told you about the $1,500 limit was probably thinking of married filing separately status, which does have that lower limit. But even then, it's only for the annual deduction against ordinary income, not the carryover amount. Keep good records of your losses and carryovers - Form 8949 and Schedule D are your friends here. And don't let the complexity scare you away from investing. Once you understand these rules, they actually work in your favor by letting you smooth out gains and losses over multiple years.

Pro tip for everyone confused by box 14: Take a picture of your W-2 and email your HR department asking them to explain each item. I did this and got a detailed breakdown within a day. Much easier than trying to guess what these abbreviations mean! Employers use all kinds of weird internal codes and abbreviations that aren't standardized. My box 14 had "DCARE" which turned out to be dependent care FSA contributions, but I never would have guessed that.

I had a similar situation last year with multiple confusing codes in box 14. What really helped me was creating a spreadsheet with all the abbreviations from my W-2 and then systematically looking each one up. Some common ones I've encountered: "PARK" (parking benefits), "TRANS" (transit subsidies), "HLTH" (health insurance premiums), and "401K" (sometimes used for additional retirement plan info). One thing to keep in mind is that even if you select the wrong category in TurboTax, it usually won't cause major issues since most box 14 items are informational rather than affecting your actual tax calculation. The IRS mainly uses this box for tracking purposes and to ensure everything matches up with what your employer reported. If you're really stuck and don't want to contact HR, try looking at your benefits enrollment documents from the beginning of the year - they often use the same abbreviations that show up on your W-2.

Don't forget that HSA contribution limits are prorated if you don't have eligible HDHP coverage for the full year! Made that mistake once and had to withdraw excess contributions. Painful lesson.

Great question! Yes, you absolutely still get tax benefits from post-tax HSA contributions. Even though you're not getting the immediate FICA tax savings like you would through payroll deduction, you can still deduct the full contribution amount on your tax return as an above-the-line deduction. This reduces your adjusted gross income dollar-for-dollar. The key advantage over paying medical expenses directly out of pocket is that HSA funds grow tax-free and come out tax-free for qualified medical expenses. Plus, there's no "use it or lose it" rule - your money rolls over indefinitely. You can even invest HSA funds for long-term growth if your provider offers investment options. Just make sure to keep good records of your contributions and save all your medical receipts. You'll need to report contributions on Form 8889 when filing taxes. Your HSA provider will send you Form 5498-SA showing your total contributions for the year.

This is a complex situation that touches on several tax areas. Based on what you've described, here are the key considerations: **Interest Deductibility**: Unfortunately, the interest on your loan likely won't be deductible. Since your bonuses are paid through payroll as W-2 income, they're considered compensation rather than investment income. This means the interest won't qualify as "investment interest expense" under Section 163(d). **Alternative minimum tax (AMT) considerations**: Even if some portion were potentially deductible, you'd need to consider AMT implications, especially as a high-income earner in NY who itemizes heavily. **Documentation is crucial**: Whatever you decide, make sure you have clear documentation showing the business purpose of the share purchase. Keep your employment agreement, shareholder agreement, and loan documents organized in case of questions. **State vs Federal**: While federal deductions may be limited, some states have different rules. NY sometimes allows deductions that aren't available federally, so check with a local tax professional. Given the 8.75% interest rate and limited deductibility, you might want to run the numbers on alternative financing (HELOC, margin loan, etc.) before committing to the company financing. The potential bonus income sounds attractive, but make sure you're not overpaying for the privilege due to non-deductible interest costs. Have you calculated what your effective after-tax return would be considering the loan interest and your marginal tax rate?

Great question about employee stock purchase plans! Unfortunately, the special tax rules for ESPPs (like those under Section 423) only apply to publicly traded companies, so your situation wouldn't qualify for those benefits. However, there's another angle worth exploring that I haven't seen mentioned yet - the potential for Section 1244 treatment if things go south. Since this is a closely-held C-corp, if the shares ever become worthless or you sell them at a loss, you might be able to claim up to $50,000 ($100,000 if married filing jointly) as an ordinary loss rather than a capital loss under Section 1244. This requires the corporation to meet certain requirements (generally small business stock issued for money or property), but it could provide better tax treatment than the capital loss carryforward situation that Nia mentioned. The ordinary loss deduction would be fully deductible against your income in the year of the loss, rather than being limited to $3,000 annually. You should verify with the company whether their stock qualifies as Section 1244 stock - many closely-held corporations structure their stock issuances to meet these requirements specifically for this tax benefit. Also, regarding your HELOC idea - that's smart thinking. Just make sure you can handle the payment obligations on both the HELOC and your regular expenses if the bonus income doesn't materialize as expected. The share-based compensation sounds promising, but it's still tied to company performance.

As a former payroll specialist who dealt with these Section 125 configuration issues regularly, I'd recommend being very specific in your initial communication with HR/payroll. Don't just say "my W-2 is wrong" - that could mean anything and often gets put in a pile. Instead, try something like: "My HSA contributions made through payroll deduction under our Section 125 cafeteria plan are incorrectly included in Box 5 (Medicare wages) on my W-2. Per IRS Publication 969 and IRC Section 125, these contributions should be excluded from all FICA taxes including Medicare. This appears to be a payroll system configuration error that may affect other employees as well." The key phrases that usually get immediate attention are "Section 125 cafeteria plan," "IRS Publication 969," and especially "may affect other employees." That last part is crucial because it signals this could be a systemic issue requiring broader correction, which makes it a priority for the payroll department rather than a one-off employee complaint. Also, if you have access to your pay stubs, include one that shows the HSA deduction coded as pre-tax. This gives them concrete documentation to reference when they're troubleshooting their system setup.

I wanted to add a few practical tips for anyone dealing with this HSA/Medicare tax issue based on my experience as a benefits administrator: 1. **Timeline matters**: If you're filing your 2024 taxes soon, don't wait for the employer to fix the W-2c. You can file correctly using the adjustment method mentioned by others and still pursue the corrected W-2 separately. 2. **Document everything**: Keep copies of all communications with your employer about this issue. If they're slow to respond, this documentation helps if you need to escalate to the IRS. 3. **Check multiple years**: This type of payroll system error rarely happens in isolation. If they got it wrong for 2024, check your 2023 and 2022 W-2s too. You can still get refunds for prior years within the statute of limitations. 4. **Know your numbers**: Calculate exactly how much you overpaid before contacting HR. For HSA contributions, it's simply your total annual HSA contribution × 1.45% (Medicare tax rate). Having the specific dollar amount makes your case more compelling. The silver lining is that once employers realize this affects their own matching tax obligations, they tend to fix these issues pretty quickly!