I mean the "in VPN" Checkbox which you can mark by adding a route. So by adding the route you say the meraki over which router it can reach this specific network. For example you got a router A and router B, router A has a route to B and knows which subnets are behind this specific router. Let's suppose your Meraki is behind router A. You need to let the Meraki know which subnets can be reached through router A, otherwise it only knows about the directly connected ones. I've made a little drawing to hopefully clear things up a little 🙂 If you take my drawing your routing table would look like this (with static routing): Meraki: 192.168.10.128/25 -> Router A 192.168.0.0/24 -> Router A 172.16.0.0/16 -> Router A 10.0.0.0/8 -> Router A 192.168.20.128/25 -> directly connected Router A (the left one): 192.168.10.128/25 -> directly connected 192.168.0.0/24 -> Router B 172.16.0.0/16 -> Router B 10.0.0.0/8 -> Router B 192.168.20.128/25 ->Meraki Router B (the right one): 192.168.10.128/25 -> Router A 192.168.0.0/24 -> directly connected 172.16.0.0/16 -> directly connected 10.0.0.0/8 -> directly connected 192.168.20.128/25 -> Router A And then you should be able to reach the Server 🙂 Have you already tried to ping the Server from the Meraki connected to the network of it? If the ping is possible you can add the Network to the Site-2-Site Firewall rules and this will create the route described above 🙂 Also your daily dose of kb and routing https://documentation.meraki.com/MX/Networks_and_Routing/MX_Routing_Behavior#Route_Priority
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