Recently on a flight, I had some major frustrations with the in-flight wi-fi experience. The damn thing just would not work. The culprit? I had hard-coded the DNS servers on my laptop to Cloudflare's 184.108.40.206 and 220.127.116.11. Removing these let the in-flight wi-fi experience work. I would still suggest setting up a vpn whose DNS servers are hard-coded to Cloudflare and using that once you're connected. The additional latency should be marginal, especially if you choose a server to host your VPN that is near Chicago -- GoGo's home base and presumably the point packets get routed through on their way back to your seat in the sky. Legal ramifications aside, it would be pretty easy to spoof Gogo's network on aircraft and man-in-the-middle things as the network is unsecured and uses captive-portal garbage like starbucks.