I am trying to add similar functionality. I have a checkbox field (Review Required) with 2 values (yes, no). I want to automatically transition the issue to Review if that field has a value of 'Yes' selected, however when I add logic similar to the logic above, I still have to click a button rather than it automatically transitioning at the step in the workflow I need it to.
Field to be checked: Review Required Target field to be set: Issue status (delayed writing)
Yes (In Review) No (Close)