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Published Sep. 10, 2025

Unable to send message: Could not convert socket to TLS

Written By

Dávid Hegedüs

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Issue

  • In Fix Pack 92 we add the mail.session.mail.smtp.starttls.enable property to the portal.properties file to successfully configure the outlook mail server.
  • After installing this Fix Pack or a higher one you might receive the following error:
     
    2021-01-18 20:39:05.590 ERROR [default task-18][MailEngine:128] Unable to send message: Could not convert socket to TLS 
    sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target 
    at sun.security.provider.certpath.SunCertPathBuilder.build(SunCertPathBuilder.java:141) 
    at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:126) 
    at java.security.cert.CertPathBuilder.build(CertPathBuilder.java:280) 
    at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:392) 
    at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:302) 
    at sun.security.validator.Validator.validate(Validator.java:260) 
    at sun.security.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:324) 
    at sun.security.ssl.X509TrustManagerImpl.checkTrusted(X509TrustManagerImpl.java:229) 
    at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:124) 
    at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1596) 
    at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:216) 

Environment

  • Liferay DXP 7.0

Resolution

  • Set the following property in the portal-ext.properties file:
    mail.session.mail.smtp.starttls.enable=false

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