Tearing my Hair out GogoInflight to work (part trois) on my MacBook Pro and iPhone

OK, last month, the big victory was getting Gogo Inflight to finally work on my iPhone 12 Pro Max with Alaska Airlines (I don’t know if it will work elsewhere, but it does work now). Now, the next confusing mix of solutions, but I finally got it to work by turning off NordVPN and most crucially requesting a mobile site on the phone so Gogo knew it was a phone.

iPhone set to Mobile Site and Forget the Network

The other confusing part when trying to get a phone running is that if you:

From the tips before, make sure that your VPN is off and that you have the magic site, https://alaskawifi.com set to Mobile Site Requested
Do not set AlaskaAir as your default network because on your phone skips the step that gets you to the magial Alaska WiFi network.
When you click on this, you should get the dialog that says click on Other and the Use without Internet
We actually found this incredibly unreliable to make work. Sometimes you would get the dialog and sometimes you wouldn’t. The magical thing happening is the redirection from the friendly name to sometime like https://captive.gogoinflight.com or https://airbornemedia.gogoinflight.com

On your MacBook Check your DNS Settings

OK, I was even more frustrated on my MacBook, but the steps are:

Turn off or VPN or trust it the network
Turn off DNS overrides. The way the system works is that there is a local DNS which spoofs and automatically rewrites requests like alaskawifi.com, so it turns out that something in all my configuration actually went and hard set the DNS address (is that scary), so you don’t get the default so make sure to go to System Preferences/Network/Advanced DNS and make sure you only have greyed DNS Servers which means that these are the default set by the network.

Note that often times as a security measure, various applications will override the DNS setting because some ISPs (cough, Comcast) will actually hijack the DNS and send you to the site it wants (like its own custom search engine which is very confusing). But this was the last hack that worked for me.