A down year in the market can still work in your favor. Tax-loss harvesting lets you put investment losses to use against your gains, but timing, wash-sale rules, and your long-term plans all matter. This checklist walks you through the questions to ask first, from your tax bracket to whether you plan to give or pass down a security someday. See how it fits into our tax strategies and investment planning, and if you plan to give securities to causes you care about, explore our approach to charitable planning.