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Alfresco 5.1 Configure Outbound email with Office 365

Question asked by rmeske on May 3, 2016
Latest reply on Nov 11, 2016 by travisr
Hello,

I have reviewed a variety of posts regarding configuring Outbound mail to use Office 365. One implied it can't be done, and another a user was able to get it working, however I have tried the settings and am getting an error.

My settings alfresco-global.properties:
mail.host=smtp.office365.com
mail.port=587
mail.protocol=smtps
mail.from.default=test@mydomain.com
mail.username=test@mydomain.com
mail.password=mypassword
mail.encoding=UTF-8
mail.smtps.starttls.enable=true
mail.smtps.auth=true

I can telnet to smtp.office365.com 587 successfully, so I know the port is not blocked.

The error in the alfresco log is:
2016-05-03 12:18:37,864 ERROR [org.alfresco.repo.action.executer.MailActionExecuter] [ajp-apr-8009-exec-5] Failed to send email to someuser@mydomain.com : org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  nested exception is:
        javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?. Failed messages: javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  nested exception is:
        javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?; message exceptions (1) are:
Failed message 1: javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;
  nested exception is:
        javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

What else can I look at?

Regards,
Ron

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