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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 '14 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. – Karl von Randow Oct 10 '14 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 '14 at 13:18
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    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 '14 at 17:15
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    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...) – Walty Yeung Feb 4 '15 at 10:30
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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.

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protected by Community Oct 30 '14 at 13:19

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