Quote:
Originally Posted by chassis
You can sell "lots", in other words you can choose which shares you sell.
When you sell the 300 shares, you can choose whether or not to sell shares held long term or short term, given your example.
As an experiment, log into your brokerage account and go through the steps necessary to sell shares. You should come to a screen or selection where you choose "lots". This is how Fidelity's trading platform works. Schwab's appears to be similar.
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vanguard also allows you to choose which stocks to sell by buy groupings, or even FIFO