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A dumb question from a novice investor: What date does the IRS use in calculating how long you've held something and/or what year the transactions took place? For example, I bought and sold some stocks on 12/29/98. Those transactions didn't settle until 1/4/99. So how does it work?
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You have to go by the trade date, not the settlement date.
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TMFTaxes writes (in part):

As pointed out, the settlement date controls for tax purposes.

I reply:

Um, Roy, have you been getting enough sleep lately? I think you meant to say that the trade date controls. --Bob
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As pointed out, the settlement date controls for tax purposes.

Gee, Roy, here we've all been telling them it was the trade date, not the settlement date.
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<<As pointed out, the settlement date controls for tax purposes.

Gee, Roy, here we've all been telling them it was the trade date, not the settlement date.>>

WHERE THE HELL IS THAT UN-REPLY BUTTON!!!!!

As Bob and RooCat have pointed out, it's the trade date that controls.

So....Bob....how was it again that you got various posts removed again? I think that this is one that should be pulled.

Thanks again for the clarification from both of you. And thanks for being kind for such a bone-headed error.

TMF Taxes
Roy
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