Outlook crash immediately with an error message <...gpg4win does not operate correctly...Outlook will close automatically...>.
After re-start of Outlook the YOURSELF addressed encrypted message sent out correctly over the Exchange server.
Encrypt and Sign an outgoing message with BCC=YOURSELF
Windows 7 Professional SP1, EN
Office Outlook 2010 Professional SP2, DE
Exchange Server 2007 installed on Windows Server Enterprise 2008 SP2, EN