User experience issue with always-on feature

[jordankrueger]

This is a usability problem, not a technical issue. The always-on feature is causing people to not be able to connect to new WiFi networks that require sign on.

For example, a user’s OutlineVPN client is on and activated. They get onto a plane and when they’re in flight, they attempt to connect to the plane’s WiFi network. They’re able to connect to the network but not able to get the sign up/sign in for something like GoGo to connect because GoGo won’t allow the connection to the VPN before you authenticate.

I have a team of ten using Outline and numerous people have had this issue despite training on what the VPN is and how it works. Because hotel and airplane WiFi are so unreliable, the users often believe that the issue is with the WiFi network sign in before thinking about Outline, so they repeatedly connect and disconnect from the network, restart their computer, and get frustrated when others around them are able to connect or they contact the hotel support and they say everything is working properly. It’s only when they the turn off Outline (“it’s broken!”) that they can connect.

I think this is a significant deterrent to appropriate use because it results in a loss of confidence in the tool or frustration with it to the point of refusing to use it.

[bemasc]

Thanks for this detailed report. Do you know which client operating systems have exhibited confusing behavior? Each OS has different captive portal detection behavior.

[jordankrueger]

Mac OS

[trevj]

@pandemicsoul Thanks for the excellent bug report.