Auto Tagging being able Retro already existing bookings
Auto tagging doesn't do this today only works with new bookings.
Thanks for writing up this request!
We have some plans in the works that should accomplish this for you. Tag automations will apply to new bookings and existing bookings as they change.
We'd like to build out a Batch Update tool for Tag Automations in the future, but the above will get us a step closer in that direction. As a change occurs on an existing booking that was created prior to the Tag Automation, that booking will be updated with a relevant tag at that time.