"Shouldn't GP see that as part of the connection process and stop the connection vs. letting it connect?" Well, if the client can't reach the portal from inside the network, and the client connects from inside the network initially, it's not even going to get the portal config to tell it what the internal host check address is in the first place. You could also trigger this error if a users switches from an external to internal network (e.g. from mobile hotspot to corporate WiFi), and the client is configured to try to reconnect. This is also particularly problematic if you're using and "always on" connection method, as the client will attempt to reach the portal anytime. Rather than getting an error, you want it to connect to the portal to check for config updates, and then not connect to a gateway, at which point the client will say "Connected - Internal" instead of connected to a particular gateway. It's been awhile since I've done a new portal setup, so I don't recall the exact behavior, but I'm not sure you'll avoid getting the connection error if the portal isn't accessible. You should be able to experiment a little to determine what works though. Having setup portals a few different times now, I still suggest making them accessible from your internal network to avoid the most hangups and confusion to users. If you're not doing desktop SSO to pass the user's credentials to the client when they log into the OS, you can use cookies, and set the portal cookie timeout to a really high time (like a year), and use a much shorter time (like a few hours) on your gateway which is the more important thing to secure since it actually terminates the VPN tunnel. This will keep users from being prompted to authenticate to the portal when if GP tries to connect while on the corporate network.
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