Not to go too deep on the why, we have a separate site in our O365 tenant that is enabled for external sharing. This is done to ensure no accidental sharing of content.
When a user or groups wants to have an external resource, we create a LIbrary for them and break inheritance, giving the individuals access to the Library.
The Tenant allows sharing to specific domains and the external share site has the Organization settings. In all cases, this process has functioned correctly.
What we are seeing in one case is that a user is taking content that existed elsewhere and copying it to their shared library. When they do that, that content is unable to be shared with the external users, while other files from the desktop are able to be shared.
Is there a smart way to decouple the previous sharing limitations of the files and treat them as if there were new files in the sharing library.
