I set up a similar rule to turn on a bulb at 4 pm and off at 11:59 pm. This is still due to the scheduler not being able to handle past midnight conditions. It light turned on at the proper tine, but didn’t turn off. I had put the end time in the same rule as the start time. That works for a couple of other rules I have. In this case it didn’t. So I removed the rule end time and created a second schedule to just turn off the light at midnight.
Another method would be to create an “inverse” rule. That is where you turn OFF a light or plug at 1 am, for example, and end the “off” time at 7 pm. I am doing that type of schedule for my porch light and a plug that lights a couple of sculptures. They seem to work perfectly for me.
I use 7 schedule rules and 18 trigger rules. They have been working for me through all of the recent updates and changes over to the new “rules format”. I do not mean to imply the current implementation is perfect. As a former programmer, I know there is always room for improvement. But, as @Loki mentioned, your best approach is to open a service ticket and work with the tech staff to resolve your issue.
If you want help from this forum too, please post screen shots of your rules. Those are helpful to those of us who like pictures. Reading is hard.