Unable to communicate with secure web proxy on iOS 8 I am attempting to connect to a web proxy server using the Charles proxy application installed on Windows.

I have two iPhones - an iPhone 5 running iOS 8.0.2 and an iPhone 4 running iOS 7.1.2.

I have used both of these phones to connect to my proxy server (both HTTP and HTTPS) for a while now, but this is the first time I have tried to connect the iPhone 5 following the iOS 8 update.

I can connect to secure and insecure on my iPhone 4, but my iPhone 5 does not allow HTTPS and gives me this error:


I have tried installing the SSL certificate again on my iPhone 5, but this has had no effect.

Both phones have identical network configuration and I can communicate with the proxy on the iPhone 5 - just not over SSL.

The Charles error is:
SSLHandshake: Remote host closed connection during handshake
For me, Charles Proxy 4.1 works better across iOS devices.


https://www.charlesproxy.com


You might want to reset all network settings on any iOS device you have issues with and potentially do a clean wipe if you have pinned / trusted certificates that are conflicting with the ones you need for the man in the middle proxy to work.