Use Live UI to see just what the "attachments" section is looking at, and then see if that page is present. You'll probably need to run Tracer when you create the attachment to see if it successfully gets created, and then run Tracer again when rendering the screen. I don't know the actual code involved, but probably there is some sort of obj-browse (or the like) operation which is looking into all attachments and filtering only those appropriate for your work object. If the attachment is getting successfully created, then finding that filter condition and observing why your attachment is being rejected for display will probably deliver the info you need to make it render.
1. In your screenshot2, can you select a different source and see if the file is attached?
2. Does the attachment work in the Pega Platform layer? You can run OOTB flow "BasicProcess" under PegaSample-Task class and do attachment. If it works, then attachment feature is broken in Care Management framework.
3. Follow Ron's suggestion to do the debug. If you cannot find anything about the root cause, you can raise a SR. Pega GCS will further help you.
As I debugged, I came to know that the Data page that pulls the results of the attachments has a report definition sourced and that report definition has a class join. I had to change this class to our implementation class and that fixes the problem.
One question - This report definition is in Pega's Link-Attachment class. To customize this rule, should I extend the class to our implementation layer?