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Marklong wrote "My company has a stock purchase plan that deducts a fixed percentage from your pay check during the plan year, and at the end of the plan year takes the total amount deducted and purchases shares at 10% of the lower of the price of the stock on the first day of the plan year or the last day of the plan year. My question is this: at what point in time will the shares be considered long term vs. short term for capital gains treatment?"

The way you described it above, the stock is purchased at the end of the year after combining all your contributions throughout the year. Since stock is not actually purchased until the end of the year, this would be the date you start counting from for long and short term capital gains. You will have to wait at least a year in order to take advantage of long term capital gains.
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