SmartThings Hub and WeMo outlet...curious behavior

I have four WeMo smart plugs that all work perfect-- two mini, two switch. I can control all four through the SmartThings app without a problem, as well as the routines that I have setup, well almost, and this is the where I am looking for some help.

Two lights upstairs are on the two WeMo mini plugs and are scheduled M-F in the mornings to go on and off…works every time without issue. Then I have a second routine in the evening that comes on ~20-min before sunset and it turns on the same two, plus one WeMo switch plug in the family room with another light… 7-days a week. This is the routine where I am having an issue. I command the two upstairs lights to turn off at 10:30pm and the family room light off at 11:30pm. The upstairs lights will not turn off, but the family room light does. I have checked the settings, etc and cannot find anything awry in the setup. So last night I decided to remove the upstairs lights from their routine and then move them onto the family room lights routine…and right at 11:30pm… they all turned off as commanded. From looking at the history the routine to turn off the upstairs lights never is executed. If I execute it manually, it turns them off.

So that is the issue… I cannot come up with a reason that I shouldn’t be able to turn the three on at once and then turn the two upstairs off first and then the family room off on its own later. It seems redundant and not so streamlined if I have to create separate routines for the on command from the family room to the upstairs? It will be something I will try later tonight. Any thoughts?