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Originally Posted by No Pepper
Did another test and it looks like my ammy draft was being skipped over. Only draft in 7 year history was after the first year. May have to do with the set date (December, league starts in April). At 7 years, I got my first illegal roster message. And in this test I had added another minor league level. In the "Auto-Play until Event" field, it would say: 2004 Amateur draft, December 1, 2005.
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Ah, yes, I think this is a problem when league dates for a specific season span over the new year. I think you just need to change it after that first year and it should update correctly from that point on.