The wash sale rule and stock compensation
Selling company stock at a loss and receiving new shares within 30 days can disallow the loss.
The rule
A loss is disallowed if you acquire substantially identical stock within 30 days before or after the sale. The disallowed loss is added to the basis of the replacement shares.
Why equity holders trip it
RSU vests, ESPP purchases and option exercises all count as acquisitions. A regular vesting schedule can create a wash sale automatically every time you harvest a loss.
Avoiding it
Time loss sales outside the 30-day window around any vest or purchase, or suspend ESPP contributions in the quarter you plan to harvest losses.
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