

Free RSU Gap Risk Checklist
Jumpstart checklist to protect yourself from surprise taxes
A practical guide to protect yourself from surprises when your Restricted Stock Units (RSUs) vest on or around weekends/market holidays.
Why a “Weekend Cushion” Matters When RSUs vest on a holiday, the actual release, tax withholding, and any sell-to-cover trades typically happen the next market day (often Monday). That delay can create risks:
Price gap risk: Your stock can open significantly higher or lower on Monday.
Withholding mismatch: Employers often withhold at flat supplemental rates (e.g., 22% up to a wage cap, 37% above), which may be lower than your true marginal tax rate.
Sell-to-cover shortfalls: If the stock drops between the vest valuation and the sale, more shares may be sold than expected, or you can end up with a cash or margin debit.
Blackout windows and plan rules: You may be restricted from selling when you thought you could.
Settlement timing: Proceeds from sell-to-cover may arrive after taxes are recorded in payroll.
A weekend cushion is a cash buffer plus a clear plan to handle these scenarios.
What This Checklist Helps You Do
Map your vesting calendar to market holidays and blackout periods.
Confirm how your plan handles weekend/holiday vests and tax withholding.
Estimate a practical cash cushion to cover tax gaps and price moves.
Set instructions (sell-to-cover, net-settle, or scheduled sells) ahead of time.
Avoid margin surprises and ensure a smooth Monday.



