Why https request fails on Charles Proxy if SSL proxying is turned on

Question

I have installed and configured Charles proxy in my mac.

I am able to browse all http sites and see the requests in Charles but I am not able to browse https sites I get unable to connect

Safari cannot open the page because it could not establish a secure connection.

I have installed the SSL certificate as it is mentioned in Charles but all the https connections are failing

Answer 1

I had to do few extra steps to make Charles work in my Mac+iOS setup

The device which I was using was the shared between team and had multiple certificate installed for Charles, to solve the issue I tried fresh install of the certificate and it worked

Step 1 : Remove all exiting certificate

Settings > General > Profiles Check the certificate list for name starting with Charles Proxy CA Click on the Charles certificate and Remove one by one using Remove profile option

Step 2 : Install new Charles certificate

2.1 : Charles (from Mac system) Documentation -> Help -> SSL Proxying -> Install Charles root certificate on a Mobile Device or Remote browser

Capture the IP and Port details

2.2 : Go to iOS device -> Settings ->Wi-Fi -> Click on the Connected network -> Select Configure Proxy in HTTP Proxy option -> Add IP in Server and Port as 8888 with Authentication off in device

2.3 : Open safari and browse chls.pro/ssl Download the Certificate and install

2.4 : trust certificate in Settings > General > Profiles

2.5 : Toggle on the General > About > Certificate Trust Settings

Now, restart Charles. You should be able to see the traffic in Charles

Answer 2

If you are on iOS 10.3 or later, open the Settings.app and navigate to General > About > Certificate Trust Settings, and find the Charles Proxy certificate, and switch it on to enable full trust for it

Now you should be able to access SSL websites with Charles using SSL Proxying.

Look into iOS Devices section in the Charles SSL documentation for reference