That's not how it works. Wavier claim are only processed during the "midweek" sim. So you will know whether you won the claim or not before the game. Once processed, you can make the corresponding cut during the "game" sim. The one that's trickier is signing free agents during the "game" sim. In that case, if you sign someone and are over the limit, then yes, the AI will make a cut, because there is no way for you to do it, unless, as you said you do it preemptively on the assumption you will be successful with the signing. But here's the thing: if you sign someone during the "game" sim, there is no way to insert that player into your lineup anyways. So the best advice, and the reason the game is set up this way, is to sign players during the midweek, so you can add them to your depth chart before the game sim.