I am attempting to connect to a web proxy server using the Charles proxy application installed on Windows. I have two iPhones - a 5 running iOS 8.0.2 and a 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 4, but my 5 does not allow HTTPS and gives me this error: I have tried re-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.