Yes — once, and it cost me ₹1.8 lakh in extra tax. My year-three lot vested at about $47,000 worth of AMZN. I needed money for a home renovation and sold a chunk. My CA called after I sent the details. "Karthik, you sold 6 days before the 24-month mark." The entire gain was taxed as STCG at 30% instead of LTCG at 12.5%. Six days.

Morgan Stanley at Work for the shares. A note in my phone with each vest date, and a mental model of when each lot would hit 24 months. It worked for the first two years when the lots were small. Amazon's vesting is back-weighted — 5% year one, 15% year two, 40% year three. So year three is when it actually matters, and that's exactly when my system failed.

The ₹1.8L mistake made it obvious I couldn't keep tracking LTCG windows manually. I came across Rovia through a blog post about LTCG tracking for US RSUs. The dashboard shows each lot with the exact calendar date it becomes long-term. That's the thing I needed and didn't have.

Hold until LTCG, then sell for a property down payment. That's the plan. My year-four lot is my second large Amazon vest — I know the exact date it qualifies. I'll sell after that and use it toward real estate. No more selling early.

Moderate. I have a specific goal — property — and I don't want to take more risk than needed to get there. I'm not trying to maximise returns, I'm trying not to lose money to bad timing or taxes. The ₹1.8L experience made me a lot more deliberate about that.