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
Best Answer
For me, Charles Proxy 4.1 works better across iOS devices.
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.