Steven Zahm@ Ian
The issue is the cache plugin. You need to make sure the Connections page is excluded from the cache… or make sure the cache of that page is cleared after every change.
I installed User Switching for testing as other users. I left it installed as it is super handy to be able to bounce into user accounts to see what they see when troubleshooting.
I also changed the menu item for the directory from a page to a link. I linked to the directory page but added ?nocache=true the to link. That should help a little if you do not exclude the directory page from the cache. Two areas adding this link will not help is with pagination and filtering the list by character. Those links are generated dynamically and can not have the nocache query string added to the URL. The cache plugin should ignore switching categories and search because of query variables in the URL being used.
I also noticed that most your users are a custom role named “Teachers” I added the add/edit entry capabilities in Connections for that role.
I hope that makes sense and helps.