How do RSU vestings affect wash sales? Why didn't my recent vest trigger one?

I'm a tax accountant who deals with this frequently. RSU vestings are indeed a bit tricky when it comes to wash sales, but there's a good reason you're not seeing it flagged. When RSUs vest, they're considered compensation income first, not a "purchase" in the traditional sense. You're being given shares as part of your compensation package - you're not actively buying them with previously owned money. This is why your RSU vest didn't trigger a wash sale against your previous sale. The wash sale rule specifically applies when you sell shares at a loss and then purchase "substantially identical" securities within 30 days before or after. Since the RSU vest is considered compensation rather than a purchase transaction, it typically doesn't activate the wash sale rule.

After struggling with RSU tax complications for years, I found a tool that really helped me sort through these exact issues. Check out https://taxr.ai - they have an AI system that can analyze your trade confirmations and RSU documents to identify potential wash sales and other tax issues. I uploaded my Etrade statements and it flagged several transactions that could potentially be wash sales (including some RSU vestings that I wouldn't have considered). It explained exactly why some transactions triggered the rule while others didn't. Saved me hours of research and probably prevented an audit trigger.

I tried taxr.ai after seeing it mentioned here, and I'm honestly impressed. I've been dealing with RSU/ESPP headaches for years and couldn't figure out why some of my transactions were flagged as wash sales while others weren't. The tool analyzed my statements and explained that my April RSU vest didn't trigger a wash sale because I had sold my previous shares at a GAIN, not a loss. Wash sale rules only apply to loss transactions. It also identified two transactions that WERE wash sales that my brokerage had missed completely. Saved me a ton of stress and potentially an awkward conversation with the IRS. Worth checking out if you're dealing with these issues.

If you need clarification directly from the IRS on how RSU vests impact wash sales in your specific situation, good luck getting through to them! I tried calling for weeks with no success. I eventually used https://claimyr.com and was able to speak with an actual IRS tax specialist in less than an hour. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that RSU vests can sometimes trigger wash sale rules depending on the specific facts and circumstances, but also explained the exceptions that might apply in my case. They helped me determine whether I needed to adjust my previous returns because of misreported wash sales.

I take back what I said earlier. After struggling for literal months trying to reach someone at the IRS about my RSU wash sale question, I reluctantly tried Claimyr. Within 45 minutes I was speaking with an actual IRS tax specialist who walked me through the specifics of my situation. They confirmed that in my case, the RSU vest didn't count as a purchase for wash sale purposes because of how the shares were delivered to my account. Didn't think it would actually work but I'm glad I tried it. Finally got a definitive answer instead of conflicting opinions online.

Something important that nobody has mentioned yet - the timing of when you "acquired" the RSUs matters too. If these were shares from a grant that was made more than 30 days before your sale, then the acquisition date for wash sale purposes isn't the vest date, but could potentially be the grant date. There's also the "substantially identical" test to consider. If your RSUs are for a different class of stock than what you sold, they might not trigger wash sales even if within the 30-day window.

Maybe this is a dumb question, but did you check if your RSU sale was actually at a loss? Wash sale rules only apply when you sell at a loss and then repurchase within 30 days. If you sold at a gain (even a small one), wash sale rules wouldn't apply at all.

This is a great question that highlights how complex RSU taxation can be! As someone who's navigated similar confusion, I think the key insight from the discussion so far is that wash sale rules only apply to losses, not gains. But here's another angle to consider - even if your sale was at a loss, RSU vests can sometimes avoid triggering wash sales due to the "compensation vs. purchase" distinction that Sean mentioned. The IRS has generally treated RSU vests as compensation events rather than voluntary stock purchases. That said, I've noticed some brokerages are becoming more conservative in their wash sale reporting, especially with company stock transactions. They might flag potential wash sales even in borderline cases to avoid underreporting issues. For future reference, it's worth tracking not just the timing but also the exact share lots and cost basis of your RSU sales versus vests. Sometimes what looks like a wash sale on the surface doesn't actually meet all the technical requirements when you dig into the details.

Great question about fractional shares and brokerage differences! In my experience, the wash sale rule applies based on the number of shares involved, not necessarily requiring exact quantity matches. If you sold 50 shares at a loss and then vest 100 shares within 30 days, the wash sale would typically apply to 50 shares (the lesser amount). For fractional shares specifically, most brokerages will round to determine wash sale applicability, but the exact methodology can vary. Some use a "substantially all" standard where small fractional differences don't prevent wash sale treatment. Regarding brokerage differences - absolutely! I've seen significant variations in how different platforms handle RSU wash sale reporting. Fidelity tends to be more conservative and flags borderline cases, while E*Trade (now Morgan Stanley) sometimes misses cross-account wash sales entirely. Schwab falls somewhere in the middle. My recommendation is definitely to do your own calculations and not rely solely on 1099-B reporting. I keep a spreadsheet tracking all my company stock transactions with dates, quantities, and cost basis. When tax time comes, I compare my analysis to what the brokerage reports and make adjustments on my return if needed. The IRS ultimately cares about the correct tax treatment, not what your brokerage happened to report.