Based on what @rossko57 says, I would suggest to send a postUpdate instead of a sendCommand to your Flag items.
Then I see in the rule “Evening time started” a Thread:sleep of 10 seconds! Use it only for max 500ms (see Why have my Rules stopped running? Why Thread::sleep is a bad idea)
And maybe a typo but sendCommand(gEveningLights, ON) won’t work, the action sendCommand only accept strings. My advise is to use Item.sendcommand → gEveningLights.sendCommand(ON) (see Textual Rules | openHAB)
The typo and the Thread:sleep can cause unpredictable outcomes, such as a Flag item which set its self 