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Apparently, retry handling for the "connetion refused" case does not yet work properly.
I do observe the following stack trace whenever the SMTP server is unreachable:
javax.mail.MessagingException: Could not connect to SMTP host: mail.example.net, port: 25;
nested exception is:
java.net.ConnectException: Connection refused
at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1934)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:638)
at javax.mail.Service.connect(Service.java:295)
at javax.mail.Service.connect(Service.java:176)
at javax.mail.Service.connect(Service.java:125)
at javax.mail.Transport.send0(Transport.java:194)
at javax.mail.Transport.send(Transport.java:124)
at hudson.plugins.emailext.ExtendedEmailPublisher.sendMail(ExtendedEmailPublisher.java:305)
...but I can never see a "Socket error sending email, retrying once more in 10 seconds" message.
I suspect that the root cause is that Transport.send() will not throw a SendFailedException in this case, but rather a MessagingException. However, the plugin code only catches SendFailedException.
(Tested with version email-ext-2.37.2.2, but exception type handling is identical on master.)
Could you please check?