When setting up WebHelpDesk to work with Office 365 you get the following error when setting up the smtp outgoing mail connector.
Encountered error while attempting to send email: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.1 Client was not authenticated
Tickets would get created correctly but the auto reply of ticket status would return the error and no emails would be sent. The resolution that I came up with was adding the following to the advanced email properties on the outgoing mail connector was to add the following:
mail.smtp.starttls=true.
Once I added this everything started to flow just fine.
I am publishing on the forums site in case anyone has the same issue went back and forth between Microsoft and Solarwinds on the issue. If anyone knows of a better solution let me know.