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Published Jul. 2, 2025

Could not connect to the SMTP host exceptions

Written By

Pooja Bhambani

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Issue

  • When sending emails, the error "unable to send message: Could not connect to SMTP host: smtp.office365.com, port: 587" occurs.
  • Steps to reproduce:
    1. Configure the outlook mail server to send email notifications in Liferay
    2. Sometimes, the following errors occurred while sending emails.
    unable to send message: Could not connect to SMTP host: smtp.office365.com, port: 587
    javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

Environment

  • Liferay DXP 7.3

Resolution

  • Check the email configuration options carefully first because there could be several different causes for this issue.
  • Add the below property under 'Manually specify additional JavaMail properties to override the above configuration field' in mail server configurations to establish the connection. 
    mail.smtp.socketFactory.port.fallback=true

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