I'm actually curious how anyone not a geek gets on Wifi at many coffee shops etc. Many captive portals don't seem to do anything and chrome just says "can't connect" or "cert bad". I used to go to test.com, now I go to foo.com. But I'm geek. What do all the non-geeks do?
Most operating systems have started detecting captive portals and presenting a notification. All of the modern consumer ones (OS X, Windows, Android, iOS) appear to have this detection. (I don't use it so not sure how well it works, though.)
I used to stay a lot at a hotel that would "helpfully" exempt a good number of domains from the captive browser, including whatever macs and androids use to detect connectivity...
There should really be a standard for dealing with this, like a flag on DHCP saying "O HAI you need to login here", and providing a REST endpoint that will tell the OS the status of the connection at any given time.
Bugs will happen, but it's a very simply operation, they simply load an HTTP URL that has an expected response (Google's is just a 204 No Content) and check if it matches.
1. Complain that the internet isn't working.
2. Talk to friendly geek who explains going to non Secure site forces pop-up
3. Forget that this work around applied in all cafe and not just the one were problem solved. Goto 1.