I use a lot the automation with "when start date arrives" with recurrent tasks to change the status tu "next" and update a custom field.
This automation always gave me problems but marking the box "creating new task" in the recurrence solved it.
In the last week I having already a lot of problems. The task keeps stuck in "To Do" and the start date in red. I can change manually it to Next but the next day will fail again.
To fix it I need to delete de recurrence completly and create again and wait until it fails again. I'm not sure what's the reason that makes it start failing (maybe solving it after two days?) but is extremly annoying because I use a filter with my "Next" tasks and I failed doing work because I haven't see the task.