Steven Zahm@ Matt
Generally when an admin has trouble, it has to do with their testing process. Have you followed the guidance given in the FAQ I linked to in my previous reply?
If you are certain you have and the user and the entry were linked correctly, Link is functioning correctly. There is nothing more for you as an admin to do. It is designed like this so the admin does not have to worry about the process. The only way to have Link do its thing is to have the user you wish to have linked is to have them logout and back in.
If you as an admin want to “force” the process, install the User Switching plugin. Link was made specifically to be compatible with it. You can use it to “log in” as the user and the entry will be linked as if the user had logged in themself.
If you are finding that the directory entry is not being linked, the first thing to check is the email addresses. The second thing to check is if that directory entry has already been linked to another user. If it has been linked to another user, it can not be linked to another — even if you change the email address of both the entry and the user. The link between the two is persistent.
If at this point the entry is still not being linked to the user, click the Copy action for the entry on the Connections : Manage admin page, do not save the copy yet. Open the Manage page in another tab and delete the original entry. Now Save the copy. After this, you can repeat the User Switching for “force” a link.
Hope that helps!