We have an AWS JasperServer instance, but cannot get report emailing to work successfully. We've searched this forum and StackOverflow and tried many different combinations of options. The gmail account is used by our other servers to send outgoing mail, so we know the account setup is correctly. (The submission form spam filter is rejecting my post so I'm going to start trimming content. If something seems to be missing that is important, let me know). Any pointers would be appreciated. CONFIGURATION /usr/share/tomcat7/webapps/jasperserver-pro/WEB-INF/js.quartz.propertiesreport.scheduler.web.deployment.uri=http://localhost/jasperserver-pro report.scheduler.mail.sender.host=smtp.gmail.comreport.scheduler.mail.sender.username=username@gmail.comreport.scheduler.mail.sender.password=mypasswordreport.scheduler.mail.sender.from=username@gmail.comreport.scheduler.mail.sender.protocol=smtpreport.scheduler.mail.sender.port=587 /usr/share/tomcat7/webapps/jasperserver-pro/WEB-INF/applicationContext-report-scheduling.xml <property name="host" value="${report.scheduler.mail.sender.host}"/> <property name="username" value="${report.scheduler.mail.sender.username}"/> <property name="password" value="${report.scheduler.mail.sender.password}"/> <property name="protocol" value="${report.scheduler.mail.sender.protocol}"/> <property name="port" value="${report.scheduler.mail.sender.port}"/> <property name="javaMailProperties"> <props> <prop key="mail.smtp.auth">true</prop> <prop key="mail.smtp.starttls.enable">true</prop> <prop key="mail.smtp.starttls.required">true</prop> <!-- Tried with and without this line --> </props> </property> Port 587:2014-08-12 17:46:47,862 ERROR ReportExecutionJob,quartzScheduler_Worker-1:311 - The job error notification was not completed. An error occurred while sending it.org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Can't send command to SMTP host; nested exception is: javax.net.ssl.SSLException: Server key. Failed messages: javax.mail.MessagingException: Can't send command to SMTP host; nested exception is: javax.net.ssl.SSLException: Server key; message exception details (1) are:Failed message 1:javax.mail.MessagingException: Can't send command to SMTP host; nested exception is: javax.net.ssl.SSLException: Server key at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:1420)<snip>Caused by: javax.net.ssl.SSLException: Server key at sun.security.ssl.Handshaker.throwSSLException(Handshaker.java:1202)<snip> at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:1418) ... 14 moreCaused by: java.security.spec.InvalidKeySpecException: key spec not recognised at org.bouncycastle.jcajce.provider.asymmetric.util.BaseKeyFactorySpi.engineGeneratePublic(Unknown Source) at org.bouncycastle.jcajce.provider.asymmetric.ec.KeyFactorySpi.engineGeneratePublic(Unknown Source) at java.security.KeyFactory.generatePublic(KeyFactory.java:334) at sun.security.ssl.HandshakeMessage$ECDH_ServerKeyExchange.<init>(HandshakeMessage.java:1057) at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:218) ... 24 more -------------------------Port 465:2014-08-12 17:54:44,413 ERROR ReportExecutionJob,quartzScheduler_Worker-1:311 - The job error notification was not completed. An error occurred while sending it.org.springframework.mail.MailSendException: Mail server connection failed; nested exception is javax.mail.MessagingException: Exception reading response; nested exception is: javax.net.ssl.SSLException: Server key. Failed messages: javax.mail.MessagingException: Exception reading response; nested exception is: javax.net.ssl.SSLException: Server key; message exception details (1) are:Failed message 1:javax.mail.MessagingException: Exception reading response; nested exception is: javax.net.ssl.SSLException: Server key