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I need to debug some unsuccessful CalDAV synchronization requests. I have functioning clients, so I can compare working vs broken. The traffic is SSL-encrypted, but I have the key. I have root on a box, that sees this traffic.

I have previously used tools like tcpdump, ngrep, *shark, and others to debug similar problems. This time, the SSL comes into play, and the *sharks can decrypt SSL, but I haven't yet managed to build a suitable tshark command-line, and started wondering, if there aren't more specialized/adapted tools for "Debugging pretty-printed CalDAV XML over HTTPS" in a terminal.

For the record, the working devices are Androids(with recent DavDroid), and Outlook 201* (with Free/Open Plugin). The non-working are all iDevices on 9.3.2 current as of 07/2016.

How would you do it?

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It is possible to do this without having SSL keys using mitmproxy:

  1. Launch mitmproxy
  2. Go to Android's WiFi settings and configure the HTTP proxy to be your PC's IP plus the port 8080 (by default)
  3. Open the Android stock browser and go to mitm.it. Tap the Android logo and install the certificate for "VPN & apps".

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