Thanks for sharing all this detailed QSBS information! As someone new to this community, I'm finding this thread incredibly helpful. I'm in a similar situation with a startup I joined 4 years ago that's now looking at potential exits. One question I haven't seen addressed yet - does the company need to formally certify that it qualifies as QSBS, or is this something we determine ourselves when filing? Our company lawyer mentioned something about getting a QSBS election or certification, but I'm not sure if that's required or just recommended for documentation purposes. Also, for those who have successfully claimed the exclusion - did you face any additional IRS scrutiny or audits? I'm wondering if claiming such a large exclusion automatically triggers more review from the IRS.

Great thread on QSBS! I'm new to this community but have been following startup tax issues closely. One aspect I haven't seen mentioned yet is the importance of tracking the "active business" requirement throughout your entire holding period - not just at the time of stock issuance. The 80% active business test under Section 1202(e) needs to be met during substantially all of your holding period. I've seen cases where companies started as qualifying businesses but later failed this test due to passive investments or real estate holdings growing too large relative to their active operations. For anyone holding QSBS long-term, it's worth requesting annual confirmations from your company's finance team that they're still meeting this requirement. The last thing you want is to discover at sale time that your stock lost QSBS status in year 3 due to the company's investment strategy. Also, keep in mind that if you're planning a sale in the near future, you may want to consider the timing relative to potential tax law changes. While QSBS has been relatively stable, it's always been subject to political discussions about reform.

This is exactly the situation I found myself in two years ago! Yes, unfortunately your capital gains DO count toward determining which bracket you fall into. With your $337.5K salary plus $1.01M in gains, you'll definitely be pushed into the 20% capital gains bracket for most of those gains. Here's how it works: Your ordinary income gets taxed first at regular rates, then your capital gains get "stacked" on top. The portion of gains that fits between your salary and the $492,300 threshold (about $154,800) gets the 15% rate, and everything above that gets hit with 20%. But here's what really caught me off guard - don't forget about the 3.8% Net Investment Income Tax that kicks in at your income level. So you're looking at an effective rate of 23.8% on most of those gains (20% + 3.8%). My advice: definitely make sure you're doing quarterly estimated payments if you haven't already. The underpayment penalties on gains this large can be brutal. I learned that lesson the hard way!

I went through this exact same situation last year with large capital gains from company stock, and yes, unfortunately the gains do push you into the higher bracket. The way it works is your ordinary income gets taxed first, then capital gains get "stacked" on top to determine which rates apply. With your $337.5K salary plus $1.01M in gains, you'll be well into the 20% capital gains bracket for most of those gains. Only about $155K of your gains (the portion that fills the gap from your salary to the $492,300 threshold) will qualify for the 15% rate. One thing that really helped me was using tax-loss harvesting to offset some gains. If you have any losing positions, consider realizing those losses this year to reduce your overall tax burden. Also, don't forget about the 3.8% Net Investment Income Tax that applies at your income level - so you're really looking at 23.8% effective rate on most gains. Definitely recommend making quarterly estimated payments if you haven't already. The penalties on underpayment for gains this large can be significant. The safe harbor rule (paying 110% of last year's tax) might be your best bet to avoid penalties while you figure out the exact amount owed.

Based on all the helpful responses here, it sounds like your broker is correct and you just missed the mark by one day. The "more than one year" rule is really strict - it has to be the day after the anniversary of your purchase date. For future reference, I've found it helpful to set calendar reminders a few days before the one-year mark so I don't accidentally sell too early. Even though it seems like 365 days should be enough, that extra day makes all the difference for tax purposes. Since your broker already reported it as short-term on the 1099, you'll need to report it that way on your return to avoid any IRS matching issues. It's frustrating when you're off by just one day, but at least now you know the exact rule for next time!

This is such a common mistake that catches so many investors off guard! I learned this the hard way a few years ago with some Apple stock I thought I'd held long enough. One thing that might help going forward is to think of it as needing to hold until the day AFTER the anniversary of your purchase date. So if you buy on November 15th, you need to hold until at least November 16th of the following year to qualify for long-term treatment. The tax difference can be significant too - short-term gains are taxed as ordinary income (potentially up to 37% for high earners), while long-term rates max out at 20% for most assets. That one extra day of holding could have saved you quite a bit depending on your tax bracket. Unfortunately, since your broker has already issued the 1099 reporting it as short-term, you'll need to report it that way on your return. But definitely keep this rule in mind for future trades!

Got through this exact situation. Filed February 3rd. Return stuck for verification. Former employer never sent W-2 info to SSA. Called IRS April 12th. Submitted Form 4852 with final paystub. Refund received May 9th. Total 95 days. Worth the wait.

Based on my experience helping clients through similar situations, I'd recommend taking a proactive approach while you wait. First, gather all supporting documentation - final paystubs, direct deposit records, offer letter, anything that shows the wage amounts on your W-2 are accurate. This will be crucial if the IRS needs additional verification. Second, consider preparing Form 4852 (Substitute for Form W-2) as a backup plan, though don't file it yet since you have the actual W-2. The IRS often resolves these cases faster when they can see comprehensive documentation that supports the reported wages. Also, keep calling periodically (every 2-3 weeks) to check status - sometimes cases move through the system faster than the quoted timeframes, especially if the employer eventually does submit their data. The 120-day timeline is worst-case scenario, not typical resolution time.

Did your son have enough income to even need to file? If he made less than $12,950 in 2024, he wasn't required to file at all unless he had self-employment income over $400.

This is such a common mistake with teenage filers! I went through the exact same thing with my daughter two years ago. The good news is that it's totally fixable, though it requires some patience. From my experience, you have three realistic options: 1. **Wait for your son to file Form 1040X** - This is the "correct" way but takes 8-16 weeks to process. Your son would amend his return to indicate he can be claimed as a dependent. 2. **File your return without claiming him this year** - You'll get a smaller refund now, but you can file your own 1040X later to claim him once his amendment processes (adding even more waiting time). 3. **File for an extension** - Gives you until October to file, but delays your refund. Honestly, if you need the refund money soon, option 2 might be your best bet despite the hassle. You'll at least get some money now rather than waiting months for the full amount. One tip: Make sure your son understands the dependency rules for next year! The software questions can be confusing, but if he's still in high school and you're supporting him, you should be claiming him. Good luck!