I am currently looking for ideas to test my application for Man in the middle (MITM) vulnerabilities. I was thinking about using Fiddler or Cain to examine the network traffic to see if a MITM attack is even possible.
Here's a quick background: I have two applications that use the same stack, one runs on an external network and the other runs on an internal network and accepts authenticated connections from the external application.
I would like to test the connection to ensure that nothing can be sent over in plain text (which is where Fiddler and Cain come into play).
I wanted to see if anyone out there has done any similar testing and if you had any suggestions for testing MITM attacks. It should be noted that both applications are not web based.