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Published Sep. 10, 2025

"Unable to lookup mail/MailSession" error when sending emails

Written By

Jorge Diaz

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Issue

We have configured email delivery using the application server JNDI mail resource:

  1. Configuring in the context.xml of the application server: 
    • <Resource name="mail/MailSession" auth="Container" type="javax.mail.Session" mail.smtp.host="MY_HOST_VALUE" />
  2. And adding the following property to the portal-ext.properties file 
    • mail.session.jndi.name=mail/Session 

 But the following error appears in the logs when attempting to send emails:

2025-02-12 15:36:49.270 ERROR [liferay/mail-2][InfrastructureUtil:84] Unable to lookup mail/MailSession
javax.naming.NameNotFoundException: Name [java:comp/env/mail/MailSession] is not bound in this Context. Unable to find [java:comp].
	at org.apache.naming.NamingContext.lookup(NamingContext.java:520) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:155) ~[catalina.jar:9.0.98]
	at javax.naming.InitialContext.lookup(InitialContext.java:409) ~[?:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil._lookup(JNDIUtil.java:196) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil._lookup(JNDIUtil.java:214) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil.lookup(JNDIUtil.java:83) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.util.InfrastructureUtil._createMailSession(InfrastructureUtil.java:81) [portal-kernel.jar:?]
	at com.liferay.portal.kernel.util.InfrastructureUtil.getMailSession(InfrastructureUtil.java:36) [portal-kernel.jar:?]
	at com.liferay.mail.service.impl.MailServiceImpl.getSession(MailServiceImpl.java:97) [portal-impl.jar:?]
	at com.liferay.mail.service.impl.MailServiceImpl.getSession(MailServiceImpl.java:73) [portal-impl.jar:?]
	at jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[?:?]
	at jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) ~[?:?]
	at jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:?]
	at java.lang.reflect.Method.invoke(Method.java:566) ~[?:?]
	at com.liferay.portal.spring.aop.AopMethodInvocationImpl.proceed(AopMethodInvocationImpl.java:41) [portal-impl.jar:?]
	at com.liferay.portal.spring.transaction.TransactionInterceptor.invoke(TransactionInterceptor.java:60) [portal-impl.jar:?]
	at com.liferay.portal.spring.aop.AopMethodInvocationImpl.proceed(AopMethodInvocationImpl.java:48) [portal-impl.jar:?]
	at com.liferay.portal.spring.aop.AopInvocationHandler.invoke(AopInvocationHandler.java:40) [portal-impl.jar:?]
	at com.sun.proxy.$Proxy71.getSession(Unknown Source) [?:?]
	at com.liferay.mail.kernel.service.MailServiceUtil.getSession(MailServiceUtil.java:33) [portal-kernel.jar:?]
	at com.liferay.mail.internal.MailEngine.send(MailEngine.java:138) [portal-impl.jar:?]
	at com.liferay.mail.internal.MailEngine.send(MailEngine.java:283) [portal-impl.jar:?]
	at com.liferay.mail.messaging.MailMessageListener.doMailMessage(MailMessageListener.java:89) [portal-impl.jar:?]
	at com.liferay.mail.messaging.MailMessageListener.doReceive(MailMessageListener.java:95) [portal-impl.jar:?]
	at com.liferay.portal.kernel.messaging.BaseMessageListener.receive(BaseMessageListener.java:22) [portal-kernel.jar:?]
	at com.liferay.portal.kernel.messaging.InvokerMessageListener.receive(InvokerMessageListener.java:62) [portal-kernel.jar:?]
	at com.liferay.portal.messaging.internal.ParallelDestination$1.run(ParallelDestination.java:47) [bundleFile:?]
	at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128) [?:?]
	at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628) [?:?]
	at java.lang.Thread.run(Thread.java:829) [?:?]
Suppressed: javax.naming.NamingException: Could not create resource factory instance
	at org.apache.naming.factory.ResourceFactory.getDefaultFactory(ResourceFactory.java:74) ~[catalina.jar:9.0.98]
	at org.apache.naming.factory.FactoryBase.getObjectInstance(FactoryBase.java:87) ~[catalina.jar:9.0.98]
	at javax.naming.spi.NamingManager.getObjectInstance(NamingManager.java:341) ~[?:?]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:544) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:148) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:530) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:148) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:530) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:148) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:530) ~[catalina.jar:9.0.98]
	at org.apache.naming.NamingContext.lookup(NamingContext.java:155) ~[catalina.jar:9.0.98]
	at org.apache.naming.SelectorContext.lookup(SelectorContext.java:144) ~[catalina.jar:9.0.98]
	at javax.naming.InitialContext.lookup(InitialContext.java:409) ~[?:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil._lookup(JNDIUtil.java:196) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil._lookup(JNDIUtil.java:214) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.jndi.JNDIUtil.lookup(JNDIUtil.java:83) ~[portal-kernel.jar:?]
	at com.liferay.portal.kernel.util.InfrastructureUtil._createMailSession(InfrastructureUtil.java:81) [portal-kernel.jar:?]
	at com.liferay.portal.kernel.util.InfrastructureUtil.getMailSession(InfrastructureUtil.java:36) [portal-kernel.jar:?]
	at com.liferay.mail.service.impl.MailServiceImpl.getSession(MailServiceImpl.java:97) [portal-impl.jar:?]
	at com.liferay.mail.service.impl.MailServiceImpl.getSession(MailServiceImpl.java:73) [portal-impl.jar:?]
	at jdk.internal.reflect.NativeMethodAccessorImpl.invoke0(Native Method) ~[?:?]
	at jdk.internal.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:62) ~[?:?]
	at jdk.internal.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43) ~[?:?]
	at java.lang.reflect.Method.invoke(Method.java:566) ~[?:?]
	at com.liferay.portal.spring.aop.AopMethodInvocationImpl.proceed(AopMethodInvocationImpl.java:41) [portal-impl.jar:?]
	at com.liferay.portal.spring.transaction.TransactionInterceptor.invoke(TransactionInterceptor.java:60) [portal-impl.jar:?]
	at com.liferay.portal.spring.aop.AopMethodInvocationImpl.proceed(AopMethodInvocationImpl.java:48) [portal-impl.jar:?]
	at com.liferay.portal.spring.aop.AopInvocationHandler.invoke(AopInvocationHandler.java:40) [portal-impl.jar:?]
	at com.sun.proxy.$Proxy71.getSession(Unknown Source) [?:?]
	at com.liferay.mail.kernel.service.MailServiceUtil.getSession(MailServiceUtil.java:33) [portal-kernel.jar:?]
	at com.liferay.mail.internal.MailEngine.send(MailEngine.java:138) [portal-impl.jar:?]
	at com.liferay.mail.internal.MailEngine.send(MailEngine.java:283) [portal-impl.jar:?]
	at com.liferay.mail.messaging.MailMessageListener.doMailMessage(MailMessageListener.java:89) [portal-impl.jar:?]
	at com.liferay.mail.messaging.MailMessageListener.doReceive(MailMessageListener.java:95) [portal-impl.jar:?]
	at com.liferay.portal.kernel.messaging.BaseMessageListener.receive(BaseMessageListener.java:22) [portal-kernel.jar:?]
	at com.liferay.portal.kernel.messaging.InvokerMessageListener.receive(InvokerMessageListener.java:62) [portal-kernel.jar:?]
	at com.liferay.portal.messaging.internal.ParallelDestination$1.run(ParallelDestination.java:47) [bundleFile:?]
	at java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128) [?:?]
	at java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628) [?:?]
	at java.lang.Thread.run(Thread.java:829) [?:?]
Caused by: java.lang.NoClassDefFoundError: javax/mail/Authenticator
	at java.lang.Class.forName0(Native Method) ~[?:?]
	at java.lang.Class.forName(Class.java:315) ~[?:?]
	at org.apache.naming.factory.ResourceFactory.getDefaultFactory(ResourceFactory.java:62) ~[catalina.jar:9.0.98]
... 39 more
Caused by: java.lang.ClassNotFoundException: javax.mail.Authenticator
	at java.net.URLClassLoader.findClass(URLClassLoader.java:476) ~[?:?]
	at java.lang.ClassLoader.loadClass(ClassLoader.java:594) ~[?:?]
	at java.lang.ClassLoader.loadClass(ClassLoader.java:527) ~[?:?]
	at java.lang.Class.forName0(Native Method) ~[?:?]
	at java.lang.Class.forName(Class.java:315) ~[?:?]
	at org.apache.naming.factory.ResourceFactory.getDefaultFactory(ResourceFactory.java:62) ~[catalina.jar:9.0.98]
... 39 more

We followed this Liferay documentation to configure it:

Environment

  • DXP 2024.Q4

Resolution

According to the tomcat JDNI installation documentation here: https://tomcat.apache.org/tomcat-9.0-doc/jndi-resources-howto.html#JavaMail_Sessions
 
In the "4. Install the JavaMail libraries" sections, it is said:

Unpackage the distribution and place mail.jar into $CATALINA_HOME/lib so that it is available to Tomcat during the initialization of the mail Session Resource. Note: placing this jar in both $CATALINA_HOME/lib and a web application's lib folder will cause an error, so ensure you have it in the $CATALINA_HOME/lib location only.

So in order to solve the issue you have to:

  1. Shutdown the application server
  2. Copy the mail.jar and activation.jar files from the [LIFERAY_HOME]/tomcat-9.x.x/webapps/ROOT/WEB-INF/shielded-container-lib folder to the [LIFERAY_HOME]/tomcat-9.x.x/lib folder.
  3. Delete the mail.jar from the shielded-container-lib folder
  4. Do not delete the activation.jar file from the shielded-container-lib folder. Liferay DXP may require this library.
  5. Start the application server

The activation.jar must be copied to the tomcat lib folder because mail.jar has some class dependencies with that JAR file.

Additional Information

 

 

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