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Let's say I have a wash sale in which I sell 5000 shares for a $100 loss. I then buy 3000 shares back. Do I prorate the loss (in this case $60 of the $100), or can I carry the entire loss over (the full $100) even though I bought fewer shares?

Dusty gave you the correct answer, but let me restate it in the same way you asked the question. You prorate the loss. Each share sold keeps its piece of the loss ($.02). The shares which are washed (3000) have their cost basis increased by $.02/share ($60). The remaining "unwashed" shares generate a reportable loss of 2000 * $.02 = $40.

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