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It looks like you may have two pieces of information to deal with. I'm assuming that your employer is using qualified options as part of its ESPP. The enrollment date essentially corresponds to the option grant date. The purchase date corresponds to the exercise date of the options, and the sell date is what it is.

It looks like there were about 6 months between the grant date and the exercise date and about 8.5 months between the exercise date and the sell date.

If I've interpreted all of this correctly, then you have 2 pieces of information to deal with. First of all, if these shares did come from qualified options, then you have some income to report since you did not appear to hold the shares long enough to qualify for the tax break. This income amount should have been included in your W-2. This income represents the difference between the FMV of the shares and the price you paid when you exercised (purchased) the shares (the option price). Make sure this income is on your W-2 (somewhere).

Now that you've verified your income is there and properly reported, then you increase the cost basis in the shares by the amount of the income. This essentially raises your cost basis of the shares up to FMV on the exercise (purchase) date. I can't make the numbers in your post work out (85% of $105.81 does not equal $50.63) for your cost on the purchase date, so either I'm misreading or they are wrong. You're on your own to make the numbers work.

From there, the sell is treated just like a capital gain or loss (appears to be short term in your case). More detailed information is contained in publication 525 starting on page 7 (statutory, or qualified, options are discussed on page 8, which is what probably applies to you). The example given in the publication performs the math a little differently that I learned it, but the result is the same.

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