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The game will let you know when it is time to choose the All-Stars and the Award Winners.
You can do it manually yourself when you see the All-Stars notification and the Awards notifications.
The All-Star notice comes around midseason... and the Awards notice comes at the end of the playoffs.
I allow the AI to take care of all roster decisions... I let the AI do all of the managing except when I play the All-Star Game and the postseason playoff games.
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