Hi Sagi,
do you still want to continue the "Check for DB flag" job to continue running and checking, even if the yellow step starts running after 3 hours?
If no, define a maximum runtime of 3 hours at the "Check for DB flag" job and cancel it after 3 hours.
If yes, try using MODIFY_TASK with REMOVE_DEPENDENCY in the "Wait for 3 hours" event to remove the line between the yellow job and the "Check for DB flag" job.
"at least one status matches" does not work in this scenario, because it always waits for all it's predecessors to finish.
Regards, Markus