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In my experience the problem with roaming mode is it blocks the login page for wireless networks. IE: in a coffee shop. Maybe that's been fixed recently, but it was a giant PITA in the past.

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You could run a portal login helper in a network namespace that doesn't go through the vpn. https://www.chromium.org/chromium-os/chromiumos-design-docs/...

I suppose because of DNS servers. Shops give you own "correct" dns for showing you adds on any first request.

You can use iodine for those wi-fi hotspots that charge for access. It tunnels TCP-over-DNS

I never even thought about using a DNS based tunnel for this problem. Amazing.

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