Have you enabled diagnostic logging for Outlook ?
Open Outlook ==> Click file "options" ==>Clicl "advanced"==>Scroll down to Other, and check the box to enable troubleshooting logging. Restart Outlook.
Once enabled, several log files are generated. Most of them are found in c:usersusernameAppDataLocalTempOutlook Logging. Logging will include details for MAPI, SMTP, IMAP, and POP3 connections in cleartext.
Alternatively, have you tried thunderbird ?