Untrusted certificate warnings running guest VM from Oracle Virtualbox when WSS agent is running

Products

• Cloud Secure Web Gateway - Cloud SWG

Issue/Introduction

User is connecting to WSS using the WSS Agent

Oracle VM Virtual box running on the same Windows host

User can connect to Virtual box but but when trying to access internet from Ubuntu guest VM on Virtual box, they get certificate errors as shown below

Installing the WSS certificate in the root directory for Ubuntu did not fix the issue which still persisted

 

Environment

WSS Agent used to communicate with WSS

Oracle Virtual Box Windows Application to access guest VMs running on Oracle virtual platform

Cause

The Oracle Virtualbox Windows Application was detecting untrusted certs coming back from the Oracle guest VMs SSL communication and throwing certificate warnings.

Needed to disable SSL inspection for all IP addresses being communicated with - too large a task as no control over which back end was being accessed.

 

 

Resolution

Added WSS bypass for the following Applications from C:\Program Files\Oracle\VirtualBox\ directory :

VBoxHeadless.exe
VirtualBox.exe

Additional Information

Went through all the IP addresses that the App is talking to, and saw many failing SSL sessions.

Initially added SSL inspection bypass for the list of IP addresses being communicated with and warning disappeared, but they showed up as new sites were being accessed. 

in each case the c:\Program Files\Oracle\VirtualBox\VBoxHeadless.exe and c:\Program Files\Oracle\VirtualBox\VirtualBox.exe Apps were being SSL intercepted by WSS so we needed to add an APplication bypass for these EXE files.