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The "Automatically Schedule All-Star Game" option is intended for schedules without an All-Star Game or break. The option when enabled will make OOTP select the approximate mid-point of the schedule and insert a three-day break and schedule an All-Star Game for the middle day of the break.
If a schedule file already has an All-Star Game and break in it, then when the option is enabled OOTP gets mixed up over what exactly to do.
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