Network configuration to access wifi on planes

I am never able to connect to wifi on planes with my MacBook (or iPhone, but that's less of a problem for me). This is always frustrating because it feels like everyone around me is able to connect their phones and laptops with no issues, so I suspect my settings or configurations are to blame.

For example, on my most recent plane journey, I attempted to connect. It is listed as 'connected', but no page loaded ('err_fail'), and while the Wifi is listed as 'Connected', the LPSS server adaptor is listed as 'not connected'. I can't say I'm terribly tech savvy but while on the ground I am almost always able to connect, so I'm wondering if there is some configuring to be done to enable wifi in the sky. Google and searching here hasn't turned up anything so I appreciate any support you all can provide!