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Question by Oleksandr M. · Sep 07, 2017 at 12:45 PM · appmon 6.5 alerting agent plugins database server administration collector

Could not convert socket to TLS [EmailSender] WARNING

Hi,

Could anyone tell what does it mean those errors in Server.log?

"Could not convert socket to TLS WARNING [EmailSender]"

How to avoid it?

2017-09-03 06:41:47 WARNING [StringTable] A string could not be found in server side StringTable. Suppressing this warning for another 60000 ms.
2017-09-03 06:41:57 WARNING [EmailSender] Delaying 1000ms before starting retry 1 of 1, error: org.apache.commons.mail.EmailException: Sending the email to the following server failed : email.domain.net:25
2017-09-03 06:41:58 WARNING [EmailSender] Sending email caused an exception: Sending the email to the following server failed : email.domain.net:25
Could not convert socket to TLS
sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
unable to find valid certification path to requested target: com.dynatrace.diagnostics.server.shared.email.EmailSender a:207
org.apache.commons.mail.EmailException: Sending the email to the following server failed : email.domain.net:25
at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1421)
at org.apache.commons.mail.Email.send(Email.java:1448)
at com.dynatrace.diagnostics.server.shared.email.ImageHtmlEmail.resend(SourceFile:106)
at com.dynatrace.diagnostics.server.shared.email.EmailSender.a(SourceFile:322)
at com.dynatrace.diagnostics.server.shared.email.EmailSender.sendEmailSub(SourceFile:163)
at com.dynatrace.diagnostics.server.shared.email.EmailSender.sendEmailSub(SourceFile:110)
at com.dynatrace.diagnostics.server.ServerAccessController.sendEmail(SourceFile:5178)
at com.dynatrace.diagnostics.core.incidents.IncidentMailSender.a(SourceFile:489)
at com.dynatrace.diagnostics.core.incidents.IncidentMailSender.a(SourceFile:516)
at com.dynatrace.diagnostics.core.incidents.IncidentMailSender.a(SourceFile:410)
at com.dynatrace.diagnostics.core.incidents.IncidentMailSender.a(SourceFile:65)
at com.dynatrace.diagnostics.core.incidents.IncidentMailSender$BulkIncidentMailTask.run(SourceFile:525)
at java.util.TimerThread.mainLoop(Timer.java:555)
at java.util.TimerThread.run(Timer.java:505)
Caused by: javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
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: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 org.apache.commons.mail.Email.sendMimeMessage(Email.java:1411)
... 13 more
Caused by: javax.net.ssl.SSLHandshakeException: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.ssl.Alerts.getSSLException(Alerts.java:192)
at sun.security.ssl.SSLSocketImpl.fatal(SSLSocketImpl.java:1949)
at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:302)
at sun.security.ssl.Handshaker.fatalSE(Handshaker.java:296)
at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1509)
at sun.security.ssl.ClientHandshaker.processMessage(ClientHandshaker.java:216)
at sun.security.ssl.Handshaker.processLoop(Handshaker.java:979)
at sun.security.ssl.Handshaker.process_record(Handshaker.java:914)
at sun.security.ssl.SSLSocketImpl.readRecord(SSLSocketImpl.java:1062)
at sun.security.ssl.SSLSocketImpl.performInitialHandshake(SSLSocketImpl.java:1375)
at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1403)
at sun.security.ssl.SSLSocketImpl.startHandshake(SSLSocketImpl.java:1387)
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)
... 20 more
Caused by: sun.security.validator.ValidatorException: PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:387)
at sun.security.validator.PKIXValidator.engineValidate(PKIXValidator.java:292)
at sun.security.validator.Validator.validate(Validator.java:260)
at sun.security.ssl.X509TrustManagerImpl.validate(X509TrustManagerImpl.java:324)
at sun.security.ssl.X509TrustManagerImpl.checkTrusted(X509TrustManagerImpl.java:229)
at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(X509TrustManagerImpl.java:124)
at sun.security.ssl.ClientHandshaker.serverCertificate(ClientHandshaker.java:1491)
... 30 more
Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target
at sun.security.provider.certpath.SunCertPathBuilder.build(SunCertPathBuilder.java:141)
at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(SunCertPathBuilder.java:126)
at java.security.cert.CertPathBuilder.build(CertPathBuilder.java:280)
at sun.security.validator.PKIXValidator.doBuild(PKIXValidator.java:382)
... 36 more
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Answer by James K. · Sep 07, 2017 at 01:08 PM

Which minor version of 6.5 are you on? I see that there have been some updates over time that resolved errors that are the same as what you are seeing (>6.5.4) should have the relevant updates but you would install the latest release if it applies here.

Otherwise I see some reports that it was originally caused by your email server supporting StartTLS so when AppMon tries to connect using this it failed because of a certificate issue. Some possible fixes are listed below:

  • disable STARTTLS on your email server
  • wait until the 6.5.3 update where you can select plaintext SMTP session in the DT GUI (this can be set now in the 'connection type' field of the email services settings)
  • fix the certificate issue by importing the root certificate that signed your email server certificate into "DT_HOME/jre/lib/security/cacerts" (Oracle-provided default passphrase is "changeit")
  • edit the "<mailserver>" element in server.config.xml and set the attributes as follows: starttls="false" requirestarttls="false"

James

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Answer by Oleksandr M. · Sep 07, 2017 at 01:38 PM

HI James,

It means that the emails were sent all time no tls anyway ?

Version 6.5.16.1011

Now was set: StartTLS


tls.jpg (58.2 kB)
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avatar image James K. · Sep 07, 2017 at 01:50 PM 1
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I don't know how you had it set before, but normally this type of error would pop up after a major upgrade. If you started seeing this recently some other change most likely occurred wither in the AppMon settings or on the email server side. I'm not familiar enough to provide any details beyond what I have.

avatar image Oleksandr M. James K. · Sep 07, 2017 at 02:18 PM 0
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james,

I see that the emails come using tls:

in email headers : (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384)

Could it be problem with some clients

avatar image James K. Oleksandr M. · Sep 07, 2017 at 02:44 PM 1
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I'm not sure I understand, are you seeing all of the emails now or are only some working? I would expect it would be completely working or completely failing - the communication that setting is for is between the AppMon server and your email server, the clients don't come into play apart from conifguration.

avatar image Oleksandr M. James K. · Sep 12, 2017 at 11:28 AM 0
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James,

Thanks, that was problem in Cetrificate. If turn off the TLS, and turn on Encripted - the events gone.

Oleksandr

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