Hi UFO
For the first question, if you are just monitoring then DCM, VML, IDM and EDM will work (two tier detection for IDM and EDM). If you wish to respond (notify or block) we only support DCM and VML policy rules. (single tier detection on the agent itself)
IE(HTTPS) and Firefox(HTTPS) install a small plugin into the browser in order to get visibility of the secure traffic. Browser versions are critical - an older DLP agent will not work with the new browser versions. For example IE 8 support came in agent version 11. ie v9 support came in 11.6.3
The release notes for your version should provide supported browser verions.
If you are on a supported browser for your agent , can you try :
- sending via a website other than gmail
- sending over HTTP
this at least will narrow down the possible issues
Steve Randall