the end device works
the communications is solid and reliable
the hub is able to control that node
So this can fine tune you work towards something about the logic in the rule or (less likely) a bug in Hubitat that is preventing the rule from running properly.
To decompose further maybe you create two rules, one to turn on at sunset -20 and another separate one to turn off at 22:00 hrs.
I am like you and prefer to keep things under one rule just to organize things but while you are having troubles maybe best to divide and conquer. As your get more ideas on the root cause then you can think about merging them. I've been told before to not waste my time combining rules as rule machine can handle massive amounts of them but my old fashioned ways makes me think otherwise.
Here is an alternative way without delays and waits. Admittedly a bit busy but if the delays or waits are your problem this gets around that....
@CuriousB,
In Rule Machine 5.1 I built a Turn On at sunset-20 rule and then a Turn Off at 2200 for Su-Th and Turn Off at 2300 for Fr-Sa. They're working correctly, and the logs confirm it.
I had the Simple Auto rules running in tandem but they did not turn on the lights. I still don't know why.
I have them disabled now while I allow the Rule Machine rules to run for the next week or two.
It could be a bug in Simple Auto Rules (SAR). Although it's still available to use, SAR is no longer supported by staff. Basic Rules is the heir apparent to SAR.
Same is true for (old) Motion & Mode Lighting and its (newer) heir apparent, Room Lighting.
I had experimented with Room Lighting last year but had numerous issues and shelved that project.
So far, Rule Machine 5.1 is working as programmed and getting the job done. Does Room Lighting offer anything not available in RM-5.1?
SAR and Basic Rules were designed to be less intimidating (but also less powerful) rule engines compared to RM. Room lighting was designed to serve more specific purposes, so it's not apples-to-apples in that same way.