You can do multiple S2S VPNs from Azure, the VPNs just have to be to different Meraki networks/sites. I'm not sure what you'd achieve with multiple S2S VPNs to the same site, unless you're looking at redundancy to different Azure regions? You can also achieve the HA configuration across regions with the vMX now, so that's an alternative. Have a look at these two documents.   https://documentation.meraki.com/MX/Site-to-site_VPN/Configuring_Site_to_Site_VPN_tunnels_to_Azure_VPN_Gateway   https://documentation.meraki.com/MX/Other_Topics/Deploying_Highly_Available_vMX100s_in_Azure   ... View more