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I purchased shares of company at several different points in time within the past year. I have lost money on all three purchases. However, I have sold only a percentage of these shares and still own 50% of the shares.

My calculate my losses (which I would like to maximize for tax purposes), can I first "sell" the shares that cost the most per share - independant of the when date/sequence when I purchased these shares. Or, do I have to use a FIFO approach to calculate my cost per share.

Lose those quotation marks and the answer is "yes." Now the details.

You're stuck with FIFO for the shares you already sold since you didn't identify them at the time of sale. You may specify the shares you sell in the future. You can read about specific identification in the FAQ over there------------------------------->

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