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: enter image description here

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

  • We are seeing the exact same thing with out Blue Coat proxies that perform SSL interception. We do not have a resolution.
    – user93183
    Oct 1, 2014 at 18:19
  • I am unfortunately successfully using my iOS 8 with SSL through Charles. Can you try SSL Proxying on https://*.facebook.com/ and see whether that works in Safari on your iOS 8 device? I'm wondering if it's particular sites that are problematic. When it doesn't work on your iOS 8 device, are there any messages in Charles about what is failing? Perhaps also check the Error Log screen. Oct 10, 2014 at 1:28
  • I have just tried going to facebook.com and I get the same message, this time I am using my iPad with iOS 8. Where is the Error Log screen in Charles?
    – crmpicco
    Oct 21, 2014 at 13:18
  • 1
    After zero response from Charles support channel I ditched it and moved to Fiddler and followed the instructions here (docs.telerik.com/fiddler/configure-fiddler/tasks/…) to configure it for iOS 8 and it works well.
    – crmpicco
    Nov 26, 2014 at 17:15
  • 2
    For me, the problem is solved by resetting the settings (General > Reset > Reset Settings). It reset ALL settings, but keep the data (apps, text messasges, etc...) Feb 4, 2015 at 10:30

1 Answer 1


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.

You must log in to answer this question.

Not the answer you're looking for? Browse other questions tagged .