Yes, I understand that this is not supported, but I really appreciate the assistance of walking through it to see if there is any obvious sign why it is not working. I'm also prepared to wipe my computer and start over if any problems happen along the way.
I made the appropriate registry entry, and clicked on a non-encrypted e-mail. I did not receive the message indicated. I then tried to send both an encrypted and non-encrypted e-mail as a test. I was able to send a message unencrypted, but the Outlook buttons to encrypt and/or sign disappeared in debug mode so I could not send an encrypted message. This is the result of the log:
11:16:25 Email Verbose Connection accepted
11:16:25 Email Debug Queueing socket 0x9F8 for worker
11:16:25 Email Debug Socket 0x9F8 dequeued by worker
11:16:25 Email Debug Received OIPCINIT
11:16:25 Email Debug >> PGPocInitIndirectSession
11:16:25 Email Debug Session-type: LSP
11:16:25 Email Debug Email port redirection enabled
11:16:25 Email Debug << PGPocInitIndirectSession
11:16:25 Email Debug PGPocInitIndirectSession succeeded
11:16:25 Email Debug Sending OIPCINITRESP
11:16:25 Email Debug Closed client socket: 0x9F8
11:16:25 Email Verbose Connection accepted
11:16:25 Email Debug Queueing socket 0x9FC for worker
11:16:25 Email Debug Socket 0x9FC dequeued by worker
11:16:25 Email Debug Received OIPCINIT
11:16:25 Email Debug >> PGPocInitIndirectSession
11:16:25 Email Debug Session-type: MAPI
11:16:25 Email Debug << PGPocInitIndirectSession
11:16:25 Email Debug PGPocInitIndirectSession succeeded
11:16:25 Email Debug Sending OIPCINITRESP
11:16:25 Email Debug Received OIPCCONNECT
11:16:25 Email Debug >> PGPocInitIndirectConnection
11:16:25 Email Debug << PGPocInitIndirectConnection
11:16:25 Email Debug PGPocInitIndirectConnection succeeded
11:16:25 Email Debug >> PGPocProxyConnection
11:16:25 Email Verbose Processing plugin requests
11:16:25 Email Debug >> sPluginIPC
11:16:25 Email Debug >> PGPocTrayCopyLocalKeyCachesToWorker
11:16:25 Email Debug << PGPocTrayCopyLocalKeyCachesToWorker
11:16:25 Email Debug PlugIn: first event
11:16:25 Email Verbose Outlook Plugin: Loaded successfully.
11:16:25 Email Debug Received testconnection request
11:16:25 Email Debug Outlook Plugin: Version 15.0.0.4420
11:17:06 Email Verbose Connection accepted
11:17:06 Email Debug Queueing socket 0xA00 for worker
11:17:06 Email Debug Socket 0xA00 dequeued by worker
11:17:06 Email Debug Received OIPCINIT
11:17:06 Email Debug >> PGPocInitIndirectSession
11:17:06 Email Debug Session-type: LSP
11:17:06 Email Debug Email port redirection enabled
11:17:06 Email Debug << PGPocInitIndirectSession
11:17:06 Email Debug PGPocInitIndirectSession succeeded
11:17:06 Email Debug Sending OIPCINITRESP
11:17:06 Email Debug Closed client socket: 0xA00