I had the exact same issue today with Systems Manager, I tried removing the Meraki Server from AC2 and then re-added the server, and it magically started to work again.   Thanks for your help Jared. @jared_f wrote: AC2 can be a real pain. Here is usually the stuff that causes this error:   ~When you are going through setup make sure you disable the option to "Activate and complete enrollment".    ~Also, delete your server under "Apple Configurator 2" > "Preferences" > "Servers" and re-add.   ~Make sure you are grabbing the right Meraki link   ~Is the WiFi WPA2 Enterprise (user/pass & cert.)? -- that seems to not cooperate sometimes.   ~Purge AC2 program and files and re-start.   Jared   ... View more