Overview

This article addresses an issue where the on-premise Jive application fails to send emails after the implementation of a new email server, and the following error message is generated:

ERROR com.jivesoftware.community.mail.outgoing.EmailManagerImpl - Email senders are still failing javax.mail.MessagingException: Could not convert socket to TLS   nested exception is:                 javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target                 at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1230)                 at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:378)                 at javax.mail.Service.connect(Service.java:291)                 at com.jivesoftware.util.SmtpProxy.connectToSmtpServer(SmtpProxy.java:296)                 at com.jivesoftware.util.SmtpProxy.send(SmtpProxy.java:228)                 at com.jivesoftware.community.mail.outgoing.EmailSender.run(EmailSender.java:80)                 at com.jivesoftware.community.mail.outgoing.EmailManagerImpl$EmailHandlerThread.run(EmailManagerImpl.java:421) Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target                 at sun.security.ssl.Alerts.getSSLException(Alerts.java:192)                 at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1959)                 at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:302)                 at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:296)                 at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1514)                 at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:216)                 at sun.security.ssl.Handshaker.processLoop(Handshaker.java:1026)

Additionally, the email server configuration causes the application to crash with the below exception:

Error message "Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target"

Root Cause

The issue is related to the SSL handshake, where Jive cannot find a valid certificate for the email server configured.

Resolution

To resolve this issue, you need to upload the certificate to the Java KeyStore. The default location for the Java KeyStore is $JAVA_HOME/jre/lib/security/cacerts.