I don't know of a way to see when a tag was added, but can you post some screenshots of the challenges you're having so we can try to see what's going on?
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There is a way with DES to see who, when, where tags are added. Use a filter for Action and select for ACTIVITY_TAG_DOCUMENT (or whatever content type the user created). Click on preview data, then download the content csv for document and user information.
Available content tag actions are:
Note that this does not show which tags were added but this might help you with troubleshooting.
Thank you. I haven't had much success with DES, but I will try again.