Employee stock purchase plans can make buying company stock feel like an easy win, especially when a discount is involved. But before you enroll, it’s important to understand the tax rules, holding periods, and risks that can turn a promising perk into a costly mistake.

The wash-sale rule can turn what looks like a smart tax move into a missed deduction if you repurchase the same or a substantially identical investment too quickly. Learn how the rule works so you can avoid surprises and make better tax-loss harvesting decisions.