Wash sale planner Plan around a future date
An option expiring, shares vesting, a sale you have in mind? See the last safe day to sell at a loss before it, and when it would be safe again after. Free, no signup.
Your safe days show here
Pick what happens and when.
How it works
Plan around the wash sale window before it opens
Any buy of a stock counts against a loss sale of it in the 30 days before or after. When you know a buy is coming, the window is already set around that date.
Sell at a loss on or before the last safe day, 31 days ahead of the event, or wait until day 31 after it. Weekends and market holidays count as days. When the last safe day lands on one, it moves to the trading day before. When the first safe day after does, it moves to the next trading day.
Questions
Planner questions
Does a short option that expires worthless trigger a wash sale?
No. When an option you sold expires worthless, you keep the premium. That is a gain, and only losses can be washed. The risk is assignment: if a put you sold is assigned, you buy the shares that day, and that buy can wash a loss sale of the same stock in the 30 days before or after it. A call you sold that is assigned sells your shares instead.
What is the last safe day to sell at a loss before a future buy?
Count back 31 calendar days from the buy. A loss sale 30 days before still counts, so day 31 before is the last one outside the window. If that day is a weekend or a market holiday, the last day you can trade is the trading day before it. Example: for a buy on Fri Jan 15, 2027, the last safe day is Tue Dec 15, 2026. After the buy, the first safe day is Tue Feb 16, 2027 (Feb 15 is Presidents' Day).
Do a dividend reinvestment or a stock vest count as a buy?
Yes. A dividend reinvestment, shares that vest, or an automatic buy is a purchase, even a small one. If it lands in the 30 days before or after a loss sale of the same stock, it washes the loss on that many shares. Turn off reinvestment on that ticker in every account before you sell at a loss.
Can I plan around an option I bought that will expire worthless?
Yes. An option you bought that expires worthless is a loss on the expiry day. Buying the same option again, and likely the shares, in the 30 days before or after could wash that loss. Pick "An option I bought expires" and "Buy" in the planner to see the last safe day to buy before it and the first safe day after.