Many organizations have varying levels of network security. Understanding how the network traffics from your device to Apple and Jamf is key to seeing what roadblocks are getting in the way. This 2019 Jamf Nation User Conference video covers device communication and how things like proxies and SSL inspection can prevent a seamless and positive experience.
Link:
https://www.jamf.com/resources/videos/mdm-not-working-was-it-the-proxy-its-always-the-proxy/
Slides link:
https://speakerdeck.com/jamf/mdm-not-working-was-it-the-proxy
