I believe your pipeline is incorrect.
rule “Between 6 PM and 6 AM”
when
( to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) >= 0 AND to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) <= 6 ) OR
( to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) >= 18 AND to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) <= 0 )
then
set_field("trigger_workhours_off", true);
end
Greater then 6 and less then 6:30, see if that works.
Remember it military time.
( to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) >= 6 AND to_long(to_date($message.timestamp, "American/Chicago").hourOfDay) <= 6:30 )
EDIT: