Are there triggers that are not shown? This rule will only run at 07:55 and 15:55, both of which are before 16:00 and after 06:00 so that if should not run.
You could improve the rule trigger too. I think the Time is <item> rule trigger was added by 3.3. But you could put a DateTime Item, or a few DateTime Items on your MainUI where you can have a nice date/time picker (see DateTime Standalone Widget and DateTime List Item) where you enter the times and then your rule will trigger based on the state of that Item(s).
That would be a bit more user friendly than manually adding constantly changing cron expressions to a text based rule.