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.

Tax-loss harvesting lets investors turn market downturns into a potential tax benefit by selling losing investments and using those losses to offset taxable gains. Done carefully, it can lower your tax bill while keeping your long-term investment plan on track.