I had been using Charles to proxy traffic from my iPad (iOS 9.0.1) on Chrome and Safari for some time but for some reason it has stopped working.
I recently updated Charles to the latest version and regenerated the SSL certificate (as it warns you must be done) so am now running version 3.11.2.
Safari works just fine - it seems to recognise the certificate. But with Chrome pulling the option to navigate to a link even if the connection is not private in a recent update to their browser(s), I am left unable to proxy anything.
Interestingly, using Chrome on my Samsung Galaxy S5 still allows for proxying through Charles. The Samsung and iPad are both using the same proxy, and same cert, so I know it's not a config issue. It's something to do with Chrome on iOS.
Has anyone figured out a way around this?
To answer it in short: Chrome on iOS ignores root CA certificate.
You could find more information here (the latest update said that it was fixed on M-48, which is using WKWebView on iOS 9+).