Il 02/07/20 19:54, Selva Nair ha scritto:

 1. The DNS of my LAN (i.e. my home router's IP) has been set as
    default gateway for the OpenVPN interface. But I'll need to
    remember changing it if I connect from elsewhere.

That looks like a strange setting but probably doesn't hurt.

I'm not sure I understand myself how this setting is involved, but it is actually required: if I remove it I'm back at the starting point with the failed NCSI check.

I also captured network traffic to investigate, and with the gateway setup I can see a successful DNS query to the VPN DNS (not my gateway) for dns.msftncsi.com, while without it I see no trace of this query.

Such weakening of the server-side firewall shouldn't be required as you are not sending any traffic to those IPs via the VPN.  When you use block-outside DNS, the DNS server pushed must be ready to do all name resolutions for you. If it's doing that, and in particular resolving those dns.msftncsi.com <http://dns.msftncsi.com/> etc involved in ncsi, you should be good.

Probably Windows is doing something weird behind our backs. Have you tried setting a direct route via your router to those two IPs on your machine (instead of on the server-side firewall)? "route add 131.107.255.255 mask 255.255.255.255 192.168.1.1" etc.

Indeed this is weird.
I tried adding the routes (and deleted the equivalent ones to the other gateway, pushed by the server), but it didn't work.

Marco
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