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Incoming Mail Server and Mail Handler Not Authenticating with O365

Jasun Aubert May 16, 2022

I am in the process of getting our ticketing system switched over (we were using OSTicket). It was easy enough to link our current help desk email address (helpdesk@domain.com). I was also setting up the incoming mail server with the help desk account creds, IMAP, port 995 (secure IMAP), host name of outlook.office365.com. When I go to create the mail handler that essentially turns incoming emails into tickets, I’m getting an authentication error. When I test, the error states “javax.mail.AutheticationFailedException: AUTHENTICATE failed. While connecting to host ’outlook.office365.com’ as user helpdesk@domain.com via protocol ‘imaps” Of course I’ve googled it. Vague results with nothing I’ve tried working. I can obviously login to the account with the creds I have. IMAP and POP3 are both enabled for the account in question. I can provide more details if needed, I’m just stuck at the moment.

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