If you have the free cash to tie up in an ESPP, I generally think they are worth doing. They usually let you buy shares at a 15% or so discount of the lower of

If you have the free cash to tie up in an ESPP, I generally think they are worth doing. They usually let you buy shares at a 15% or so discount of the lower of the price on the vesting date, or the price on the initial offer date. This is typically over either a 2-year or 6-month look-back period, although I've seen other time periods as well. Some programs even let you automate that automatic-sell rule. So... if you're playing it conservatively, you can just sell the shares on the day that they are granted to you, thus realizing a guaranteed 15% increase on whatever percentage of your salary you can put in the program. There is some risk that if the company goes bankrupt, you could lose the amount invested. But I'd guess that ESPP programs are pretty senior in the debt pool, and generally management doesn't want to piss off its employees any more then absolutely necessary during a bankruptcy proceeding.