Thanks for the replies. Maybe I'm doing this wrong or not selecting the right options. This is what I'm doing(we'll use 2 extensions, 1 line and an evening time of 5 pm):

Setting ring group 1 to have operator ext, ring group 2 to have night extension. Set evening schedule for line 1 to use ring group 2 and set it to automatic (trunk answer was on yes). Set a daytime schedule for 9 am - 5 pm using ring group 1. If I remove the line appearance for the operator extension and call the line it just keeps ringing and never appears at operator. If I have the lines appear and ring on the operator extension and set the system time to 540 to test it still rings at the operator.

Am I missing something obvious?