No. of Recommendations: 0
If you bought a $100 stock at $85, your cost basis for determining capital gains or losses is $100. The $15 discount is taxable as ordinary income when you sell. Even if you sold at $100 after more than a year, your capital gain/loss is zero and you owe tax on $15 at ordinary income tax rates.

I do understand that. We have an ESPP. What I am referring to is any gain in the stock since time of purchase. Unless you are selling on the same day of purchase, there is a potential gain on the stock. With 26 paychecks where ESPP purchases are made, we tend to let the stock build.

If I had so little trust in the company's future that I would feel the immediate need to sell on each time of purchase, then I wouldn't make the purchase in the first place and would refresh the resume. Therefore, I evaluate the company's prospects and their stock like any other stock.

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