This might be relevant:

https://discussions.apple.com/thread/3415814

Seems some people have had luck by shortening the beacon interval on their iPhone (to something very short like 50ms!).

Alex

2014-09-25 12:44 GMT-07:00 Max B <maxb.personal@gmail.com>:
I just double checked and the captive portal isn't running on the exit node.

Very confusing....

On 09/24/2014 08:21 PM, Marc Juul wrote:
> I am running iOS 5.0.1 on my iphone. It's connected to peoplesopen.net from
> sudo room and has
>
>  IP: 10.1.1.192
>  Gateway and DNS: 10.42.0.99
>
> I'm not getting any connectivity, web or otherwise.
>
> However, my laptop is also connected to peoplesopen.net from sudoroom and
> has the same gateway and dns and has IP 10.1.1.246 and works perfectly.
>
> I can even ping 10.1.1.192 from my laptop and I can connect to the iphone
> via ssh and I can even connect out to the internet from my iphone from the
> command line using ssh and DNS resolve works!
>
> But when I try to do anything from the phone's GUI, web browser, or even
> IRC, it just sits there loading, trying to connect.
>
> Could this be something to do with the captive portal?
>
> Hrummm. Max if you want to borrow my phone to test you totes can.
>
>
>
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