Issues With Schedules That Cross Midnight

So, I’d have thought that this would be easy, but there is clearly a logic flaw in the software somewhere.

The desired result is simple, the plug comes on at 5:30 PM and goes off at 1:30 AM (technically the next day.)

Reading suggested that this should be easy, and that it was preferable to create a single rule for both the on and off actions. So I did.

The plug always comes on. But then it never shuts off.

I have deleted and recreated the rule, several times.

Testing indicates that as long as I keep both times on same side of midnight (5:30 PM until 11:59 PM ), the on and off happen just fine.

I am now testing split events (one rule for on and a different rule for off) to see if that works.

How does one get this to work?