Overnight time-range doesn't seem to work as advertised?

Hi - maybe someone smarter than me can help as I’m having no luck.
I have a simple plug-switch (Jasco) and I have one of those radiator-heaters plugged into it.
I’m trying to setup logic to leave the heater on during the daytime (8:30am-10:30pm).
Between 10:30pm and 8:30am - I’m trying to setup an automation routine to turn the plug-switch on for 15 minutes and then off for 15 minutes. This would cut the usage by 50% overnight - and I can vary the off-time as needed if I want it warmer or cooler overnight.
I can get the start/stop logic to work pretty simply in the automation-routine.
But once I add logic to have the time limited to 10:30pm-8:30am - everything seems to stop working.
I have 3 routines setup to try to accomplish this:
1 - at 8:31am - turn on the plug-switch.
2 - at 10:31pm - turn off the plug-switch.
3 - If 10:30pm-8:30am (next day) - every day precondition.
and if plug-switch is off for 15 minutes
then turn on plug-switch and set turn-off after 15 minutes.
The code works fine turning it on/off every 15 mins - but once I add in the 10:30-8:30 time constraint it never wakes up.
Unsure what to do next on this - I could have written a Groovy smart-app to handle this but now prefer (need to) use the supplied automation-routine interface.

This should work fine.
I have tested it with 1 minute on and another off.

check that in the third automation, that the plug condition off for 15 minutes, it is not a precondition.

You can also try turning off the plug a little later than 10:31 p.m. since the shutdown time starts counting from the first shutdown after 10:30 p.m. or try period 10:25 p.m. to 8:30 a.m. next day

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Or try fast Automations. I have selected random times.

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Hi - thanks very much for the replies and suggestions - however it seems my hub may have needed to be restarted or something similar. We had a hard power-failure here which took us offline for a long time. After power was restored and the hub came back up - the automation now seems to be working just fine.

Maybe there was something residual in the hub from earlier attempts at trying this?
Either way - I’ll know to restart my hub before I throw up the white-flag when what should work doesn’t.

Thanks again.