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Old 07-21-2013, 03:00 PM   #2
Fyrestorm3
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Join Date: Aug 2011
Location: Tampa Bay, Massachusetts
Posts: 2,928
I'm guessing you have the Update/Generate Player Pictures option set to "Every Jan. 1" instead of "Always if Needed."

League Menu -> Player and Picture Options -> Update/Generate Player Pictures on the right-hand side

Optionally, you can go to each team's Edit Colors & Uniforms page and do it team-by-team with the "Update this team's pictures NOW" button.
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