After a call with the very helpful @MacD it was determined that proceeding down the Azure AD Conditional Access [1] to be a much simpler way to achieve Office 365 without requiring a DAG. I didn’t know that was even an option from looking at the do...
I’ve got the exact same error in dag.log as reported in Patrick’s original post, and subsequent follow-up reporting that https://fqdn/dag gives a 404 despite this being an actual shortcut put in the start menu by the installer.
I have verified that t...