By default, "Emails" monitoring is turned off.
To start monitoring e-mails, please navigate to SYSTEM - Monitoring profiles, and make sure that the checkbox next to "Emails" is ticked.
After enabling the monitoring of e-mails, try sending/receiving an e-mail on the monitored PC. if the records of these sent/received emails do not appear within 10 minutes, please consider submitting MS Outlook tracking debug log to help us identify the issue.