When I try to connect to public WiFi networks that have a pop-up window to finish connecting, a notice comes down saying “A problem occurred. The webpage could not be loaded” and I am unable to fully connect.
Are there any tips on how to authenticate to a WiFi network when the authentication/authorization page won't load like that?
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Since you have a pop up, it’s almost certain the WiFi link is connecting and you are dealing with the networking side / captive portal.
One thing that sometimes helps is opening a web browser and going to http://captive.apple.com or just any web page.
Typically the security / registration / portal then lets you answer whatever questions / accept any EULA and then give you a proper IP address / DNS server / connection to the internet.
Past that, you’ll need to look at DHCP response or contact the person that supports that network to check their side.
