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There's two ways this happens.
First, if you set roles near the end of a "Simulating" period, it might not stick. When the new download happens you lose any changes that weren't made in time to be propagated to everyone.
Second, there's a bug that requires where some players/cards lose their "strategy" settings between seasons. It's always the exact same ones, so once you identify them, you can fix them at the start of each season.
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All teams retired from human management
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