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Since the entire holding was sold at one time, is there a way to avoid listing all of these fractional share purchases made over a 10 year period and simply average them and report the loss?

You don't average, you add all your purchases to come up with the total basis. Then you report the purchase date as "various" in accordance with the Schedule D insructions.

Accountant in a Box could tell you this if you could figure out how to ask it in a way that the programmer anticipated. It will, however, understand "various."

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