So we figured out the issue. The WSA was the culprit. According to TAC: Once an MR is upgraded to firmware version 28.1 or higher, it requires TCP port 443 to be open on any upstream firewalls for Meraki Device-to-Cloud connectivity.   This issue was not impacting our older model AP's due to the highest firmware they are able to update to is MR 26.8.3. Those older AP's communicated over 7351 UDP.  ... View more