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Published Sep. 10, 2025

Unable to configure Outlook

Written By

Amit Tiwari

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Issue

Steps Followed:

1. portal-ext. properties: 

mail.session.mail.smtp.auth=true
mail.session.mail.smtp.starttls.enable=true​

 2. Navigate to Server Administration -> Mail

Outgoing SMTP Server: smtp.office365.com
Outgoing Port: 587
Use a Secure Network Connection: Uncheck
Enable StartTLS: Check
Provide the outlook credentials and Save

3. Navigate to Instance Settings-> Email-> Email Sender and provide the same outlook account given in step 2 

4. Create a new user and check for the email.

Expected Behaviour: Email should be triggered at password update or user creation etc.

Actual Behaviour: Email is not getting triggered with the below error in server logs

2022-03-22 05:49:45.971 ERROR [liferay/mail-1][MailEngine:74] Unable to send message: 451 5.7.3 STARTTLS is required to send mail [BMXPR01CA0009.INDPRD01.PROD.OUTLOOK.COM]_ [Sanitized]
com.sun.mail.smtp.SMTPSendFailedException: 451 5.7.3 STARTTLS is required to send mail [BMXPR01CA0009.INDPRD01.PROD.OUTLOOK.COM]_ [Sanitized]
	at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:1388)
	at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:959)
	at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:583)
	at com.liferay.petra.mail.MailEngine._send(MailEngine.java:605)
	at com.liferay.petra.mail.MailEngine.send(MailEngine.java:386)
	at com.liferay.petra.mail.MailEngine.send(MailEngine.java:461)
	at com.liferay.mail.messaging.MailMessageListener.doMailMessage(MailMessageListener.java:99)
	at com.liferay.mail.messaging.MailMessageListener.doReceive(MailMessageListener.java:114)
	at com.liferay.portal.kernel.messaging.BaseMessageListener.receive(BaseMessageListener.java:26)
	at com.liferay.portal.kernel.messaging.InvokerMessageListener.receive(InvokerMessageListener.java:74)
	at com.liferay.portal.kernel.messaging.ParallelDestination$1.run(ParallelDestination.java:52)
	at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask._runTask(ThreadPoolExecutor.java:752)
	at com.liferay.portal.kernel.concurrent.ThreadPoolExecutor$WorkerTask.run(ThreadPoolExecutor.java:664)
	at java.lang.Thread.run(Thread.java:748)

Environment

  • Liferay DXP 7.2

Resolution

  • The observed behavior is a known issue and is fixed in fixpack dxp-5.
  • Installing Fix Packs and Hotfixes on Liferay DXP will guide you to install the Fixpack in your environment.
  • If the hotfix is required for this issue, please create a support ticket requesting the hotfix by attaching the patch details.

Additional Information

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