I had the SIM DFA two players on my team b/c I was over the roster limit when the season started (thought I had an extra cycle to fix but my team played on the official day 2 of the season but that is a different story). It has been 19 "days" and I can't do anything with the players. If I try to assign to the minors then I get an error saying that they have Major League contracts and if I try to assign them back to the majors then I get a message that they have to clear waivers first. However it has been long enough that they would have cleared. They are just stuck in limbo and I don't want to release them. Any ideas?

I haven't ever had Simmy auto designate for me, but maybe he DFAs without waivers. Check to see if they actually cleared (on the player card). You may have to manually waive them.

That would actually my guess add to how it works, because people would be even more upset if Simmy automatically waived ML players.