If you want to monitor every e-mail that leaves your company, try Silent BCC for Outlook. Once installed, the plug-in will deliver you BCC copies of all messages sent from all user accounts of a PC. E-mail senders will never know that a BCC copy was sent from their machines. They will not find Silent BCC in their Outlook, nor will they ever see a BCC address in Sent Items. The Silent BCC for Outlook leaves no traces of its work at all. It is absolutely invisible in Outlook and everywhere else in the system, there is no user interface for the user to switch off the plug-in or alter your monitoring settings. You can tweak the add-in to be copied on every outgoing e-mail or allow exceptions.