In some cases Umbrella support may request that you disable DNS encryption to see the DNS traffic between the Roaming Client and Umbrella cloud. You should have already configured your iptables as per the guide above for masquerading client connections.In normal circumstances the traffic between the Roaming Client and Umbrella is encrypted and not human readable. Double check that your iOS device can connect to the VPN and that it can access the Internet. Install OpenVPN as per DigitalOcean's guide. Set up a Linux VM of your choice (I used Linux Mint, but Ubuntu and Debian based distros work just as well with the rest of the tutorial), and download Burp Suite, preferably the JAR version as it is more portable. To contribute back to the community, here's a tutorial on how to MITM a proxy-unaware iOS >10 app! Guide on MITM'ing a proxy-unaware iOS app for iOS 10 and above Setting up the VM
This has been a rather interesting turn of events, apparently, the issue with VPN/Burp Suite method had to do with my configuration of the Burp Suite's invisible proxying (in which I neglected after troubleshooting a few times) as answered in the ServerFault question I posted previously. How does one effectively and (hopefully relatively easily) intercept HTTP(S) traffic from an iOS mobile app that does not respect system proxy settings? Attempts to replicate with OpenVPN yielded unsatisfactory results (another post on ServerFault here). Problem: I partially followed a tutorial that describes a PPTP VPN with Burp Suite, but iOS 10 and above has dropped support for PPTP. The VPN is set up on a Linux Mint VM with its network adapter bridged to my Mac's Wi-Fi card. Setup: By making a VPN that the iOS device connects to, all traffic will be routed through that VPN and into Burp Suite. Problem: All requests are HTTPS and can't be decrypted. Setup: iOS device connected via USB cable to the Mac, made a network interface on the Mac per this guide so as to capture packets direct from the iOS device by letting Wireshark read from that network interface. Problem: Only intercepts certain requests not made by Xamarin's native HttpClient API, such as Google Analytics, which is not useful in analyzing the API of interest.
The iOS device is configured to use an HTTP proxy. Setup: Burp Suite/Charles Proxy running on a Mac, with the proxy's CA certificate installed on the iOS device. I have tested the following strategies with various degrees of success (but never full success): Burp Suite and Charles Proxy The current tools I have available is a Mac with a Linux Mint VM, Xcode and iOS developer tools, Burp Suite Community Edition, Charles Proxy and Wireshark. I am trying to capture HTTP(S) traffic from a proxy-unaware Xamarin iOS application.
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