Email Delivery Failure

I have tried all of the various SMTP options for mail delivery, however, the server fails to properly send mail regardless of the method I use. It recognizes the method it is attempting to send with, but always fails with an error stating that there is no appropriate protocol.

org.simplejavamail.mailer.internal.MailerException: Third party error
	at org.simplejavamail.mailer.internal.SendMailClosure.executeClosure(SendMailClosure.java:91)
	at org.simplejavamail.mailer.internal.AbstractProxyServerSyncingClosure.run(AbstractProxyServerSyncingClosure.java:56)
	at org.simplejavamail.internal.util.concurrent.AsyncOperationHelper$1.run(AsyncOperationHelper.java:75)
	at java.base/java.util.concurrent.Executors$RunnableAdapter.call(Executors.java:515)
	at java.base/java.util.concurrent.FutureTask.run(FutureTask.java:264)
	at java.base/java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1128)
	at java.base/java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:628)
	at java.base/java.lang.Thread.run(Thread.java:829)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS
	at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1907)
	at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:666)
	at javax.mail.Service.connect(Service.java:317)
	at javax.mail.Service.connect(Service.java:176)
	at javax.mail.Service.connect(Service.java:125)
	at org.simplejavamail.mailer.internal.util.TransportRunner.runOnSessionTransport(TransportRunner.java:75)
	at org.simplejavamail.mailer.internal.util.TransportRunner.sendMessage(TransportRunner.java:48)
	at org.simplejavamail.mailer.internal.SendMailClosure.executeClosure(SendMailClosure.java:82)
	... 7 common frames omitted
Caused by: javax.net.ssl.SSLHandshakeException: No appropriate protocol (protocol is disabled or cipher suites are inappropriate)
	at java.base/sun.security.ssl.HandshakeContext.<init>(HandshakeContext.java:170)
	at java.base/sun.security.ssl.ClientHandshakeContext.<init>(ClientHandshakeContext.java:98)
	at java.base/sun.security.ssl.TransportContext.kickstart(TransportContext.java:221)
	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:443)
	at java.base/sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:421)
	at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:549)
	at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:486)
	at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1902)
	... 14 common frames omitted
05:17:06.349 [pool-24-thread-1] WARN  c.s.c.c.p.provider.EmailServiceImpl - Email cannot be delivered

It, however, properly reflects the options as I change them in the config.

DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTP)

DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTPS)

DEBUG o.s.m.internal.util.SessionLogger - starting async mail with session (host: smtp.<REDACTED>.com, port: 587, username: <REDACTED>, authenticate: true, transport: SMTP_TLS)

[matusfaro]

Try the different options for smtpStrategy config, options are SMTP, SMTP_TLS, SMTPS. This may be misconfigured.

com.smotana.clearflask.core.push.provider.EmailServiceImpl$Config.smtpStrategy=<SMTP, SMTP_TLS, SMTPS>

---

I am adding a config property for overriding the domain name, in a few hours check for version 1.5.9. Also you will be able to modify the local part as well (ie noreply@...).

com.smotana.clearflask.core.push.provider.EmailServiceImpl$Config.fromEmailLocalPart=noreply
com.smotana.clearflask.core.push.provider.EmailServiceImpl$Config.fromEmailDomainOverride=zandercraft.ca

---

There already is a config for overriding email sending name:

com.smotana.clearflask.core.push.provider.EmailServiceImpl$Config.emailDisplayName=ZanderCraft

All available configs for 1.5.8 are listed here: https://github.com/clearflask/clearflask/blob/1.5.8/clearflask-server/src/main/java/com/smotana/clearflask/core/push/provider/EmailServiceImpl.java

[matusfaro]

Hmm, the docker container has this under $JAVA_HOME/conf/security/java.security:

jdk.tls.disabledAlgorithms=SSLv3, TLSv1, TLSv1.1, RC4, DES, MD5withRSA, \
    DH keySize < 1024, EC keySize < 224, 3DES_EDE_CBC, anon, NULL, \
    include jdk.disabled.namedCurves

So it seems to be fine unless I’m misreading it.

Can you modify your docker-compose.yml file to include the following JAVA_OPTS:

  clearflask-server:
    ...
    environment:
      - ...
      - JAVA_OPTS="-Djavax.net.debug=ssl"

Then restart and look at the extra logs. You should see logs similar to the following:

Ignoring unavailable cipher suite: TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384
...

Please post the output including anything interesting around it.

The alternate option you have is to modify the docker container to comment out the jdk.tls.disabledAlgorithms in $JAVA_HOME/conf/security/java.security line and try it out. If it works, just keep using that modified container.