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If the very first scenario changes a bit the Broker A 500 shares sold on Dec 1 are all long term covered loss, whereas Broker B purchase 75 shares were on Nov 1.  If one sells the 75 shares in Broker B today, does the match still get you to the same place i.e., is there any short term vs long term gain/loss issue?  Is my understanding correct on the following:

 

"Losses on your investments are first used to offset capital gains of the same type. So, short-term losses are first deducted against short-term gains, and long-term losses are deducted against long-term gains. Net losses of either type can then be deducted against the other kind of gain." as per quoted on this message board.