If you could buy something at a discount and immediately sell it for the full price without much effort, would you do it? Participation in an ESPP could end up working out just like that. But as with all tax-related and benefit-related things, the devil is in the details. We are going to go through ESPP timelines, limits on salary deferrals and buying, and tax rules for dispositions of ESPP shares.
Wash Sale Rule and Equity Compensation: Options, RSUs, and ESPP
If you sell an asset at a loss, you might be entitled to either claim the loss as a deduction or use it to offset eligible gains. However, the wash sale rule sometimes comes into play, and it can be particularly pesky for those with multiple types of equity compensation from the same company (say, when you have those pre-IPO ISOs, there are RSUs vesting, and you also participate in the ESPP).