SocketTimeoutException when sending email With STARTTLS
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Support for Server* products ended on February 15th 2024. If you are running a Server product, you can visit the Atlassian Server end of support announcement to review your migration options.
*Except Fisheye and Crucible
Problem
When sending a test email via an STARTTLS connection mail won't be sent and the following error message is displayed:
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com.atlassian.mail.MailException: javax.mail.MessagingException: Exception reading response;
nested exception is:
java.net.SocketTimeoutException: Read timed outThe following appears in the atlassian-confluence.log
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An error has occurred with sending the test email:
com.atlassian.mail.MailException: javax.mail.MessagingException: Exception reading response;
nested exception is:
java.net.SocketTimeoutException: Read timed out
at com.atlassian.confluence.jmx.JmxSMTPMailServer.doSendWithMessageIdSupport(JmxSMTPMailServer.java:143)
at com.atlassian.confluence.jmx.JmxSMTPMailServer.send(JmxSMTPMailServer.java:88)
at com.atlassian.confluence.admin.actions.mail.SendTestEmailAction.execute(SendTestEmailAction.java:60)
Diagnosis
Environment
If you unsure you had STARTTLS mail server or SSL mail server, you can you below's tool to identify it
http://www.checktls.com/perl/TestReceiver.pl
Resolution
Since STARTTLS upgrades the connection to TLS after it has been established, the standard way of retrieving SSL certificates will not work.
Additional argument "-starttls smtp" is required in the openssl call.
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openssl s_client -debug -connect mail.mycompany.com:587 -starttls smtp < /dev/null | sed -ne '/-BEGIN CERTIFICATE-/,/-END CERTIFICATE-/p' > public.crt
jre/bin/keytool -import -alias tomcat -keystore jre/lib/security/cacerts -file public.crtℹ️ Standard certificate store password is "changeit".
Repeating this for all required certificates
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