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I participate in an ESPP which purchases company stock at a 15% discount every 6 months.  I have accumulated a few thousand shares of company stock this way.  (It is a small percentage of my portfolio.)  For the last few years, the stock has steadily declined, so I have been selling the stock as soon as it is purchased to lock in the 15% profit.  This is taxed as regular income.  Would it be better to sell an equal amount of previously accumulated stock to claim a long term loss on my taxes instead?  If I do, have I lost the 15% profit?  As a side note, I've already sold a mutual fund this year and will max out the losses I can take for this year and probably have some to carry forward. 

Maxine,

You should check this with your tax accountant but I believe you can do transactions by share lot and possibly do both. In other words, you can realize a short-term (ordinary income) profit on an immediate sale of discounted shares. You can also realize a long-term loss (capital gains income) on a sale of shares purchased over a year ago. You can do this so that the long term loss offsets the short term gain so there is zero tax liability. You could also sell more of your long term shares and realize a maximum net loss of $3,000 for the current year.

Scott