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I sold a stock in 2007 in a company I previously worked for. I bought it through a stock purchase plan over the course of several years. So I purchased small quantities at various prices through payroll deductions.

Publication 550 says “If you buy and sell securities at various times in varying quantities and you cannot adequately identify the shares you sell, the basis of the securities you sell is the basis of the securities you acquired first”. Does this apply to my situation?

Having read ahead, yes, but not the way you think. This is the standard FIFO rule if you don't identify the specific shares you sold. in your case it's moot since you sold everything.

I sold all the shares of stock, so I can identify the shares I sold. I just don’t know the cost of all the individual purchases. Do you think I can use the basis of my first purchase? Using the cost of the first purchase will result in a much larger capital loss because the stock steadily lost value.

Nice try, but no. Of course you know, or more precisely, your records know how much you paid. You just need to dig it up. Most plans provide an annual statement which would show you the totals for the year. If you can't find anything, maybe the plan can help.

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