How do you handle automation when adding existing resource to helm chart?

I'm deploying a pretty simple helm chart for some resources that get managed by an operator I have running on the k8s cluster. Updates to these resources is just a simple update to the values file and then pipeline runs helm upgrade to make changes.

I need to change some configuration of the operator which is going to bring a resource that was created and managed by the operator to being something I manage. I added this resource to my helm chart, and testing the upgrade shows that (expectedly) helm complains that it doesn't own this resource.

The fix is simple enough, which is to annotate the resource with what helm is expecting. But I'm curious about the best approach for how to do this. Would you:

  1. Manually annotate the resource then run the updated helm chart via usual automation?
  2. Update the pipeline to check the annotations and annotate as needed via kubectl, then run the rest as normal
  3. Make a separate pipeline just for this one time upgrade
  4. Another approach?

Right now things are mostly in a test environment, so doing the annotations manually is an option, but this seems like it wouldn't be a feasible approach in the future. Any advice welcome.