Even with a solid RSU strategy in place, there are a few overlooked tax and compliance details that can complicate things. Here are the core points from the lesson:
Insider trading policies may limit your ability to auto-sell or manually sell RSUs immediately upon vesting, leading to short-term gains or losses you can’t always control
Wash sale rules can disallow losses if you repurchase the same stock within 30 days of a sale, which can easily happen with monthly vesting schedules
Incorrectly reporting RSU-related wash sales on your taxes may go unnoticed, but technically violates IRS rules and can affect your cost basis going forward