Thermostat controller with portable A/C

So one more issue that I’m realizing I haven’t solved. My time restriction turns the AC off at 6am each morning, but it doesn’t turn the AC on at 9pm each night. Is this an issue with the AC driver or how I’ve configured the controller?

Here are screenshots of the time restriction from the controller, logs of the controller and driver, and events from the driver (showing when I turned it on manually at 3am on 10/22 (3rd image) and when the controller turned it off at 6am on 10/20 (4th image)).