Although I'm trying to send an email on port 25 without SSL, I'm getting an SSLHandshakeException. Below you can see debug messages printed by javax.mail.Session and the SSLHandshakeException.
Can you help me understand what's going on?
22 Dec 2009 15:13:21,054 INFO root:197 - DEBUG: setDebug: JavaMail version 1.4ea 22 Dec 2009 15:13:21,059 INFO root:197 - DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc] 22 Dec 2009 15:13:21,103 INFO root:197 - DEBUG SMTP: useEhlo true, useAuth false 22 Dec 2009 15:13:21,103 INFO root:197 - DEBUG SMTP: trying to connect to host "mail.abcdef.com", port 25, isSSL false 22 Dec 2009 15:13:21,338 INFO root:197 - 220 mail.uvwxyz.com ESMTP abcdef Mail Server v8.0; Tue, 22 Dec 2009 15:12:10 -0700 22 Dec 2009 15:13:21,338 INFO root:197 - DEBUG SMTP: connected to host "mail.abcdef.com", port: 25 22 Dec 2009 15:13:21,342 INFO root:197 - EHLO fsb160 22 Dec 2009 15:13:21,383 INFO root:197 - 250-mail.uvwxyz.com Hello fsb160 [65.124.157.54], pleased to meet you. 250-ENHANCEDSTATUSCODES 250-SIZE 250-EXPN 250-ETRN 250-ATRN 250-DSN 250-CHECKPOINT 250-8BITMIME 250-AUTH CRAM-MD5 DIGEST-MD5 LOGIN PLAIN 250-AUTH=LOGIN 250-STARTTLS 250 HELP 22 Dec 2009 15:13:21,383 INFO root:197 - DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg "" 22 Dec 2009 15:13:21,383 INFO root:197 - DEBUG SMTP: Found extension "SIZE", arg "" 22 Dec 2009 15:13:21,384 INFO root:197 - DEBUG SMTP: Found extension "EXPN", arg "" 22 Dec 2009 15:13:21,384 INFO root:197 - DEBUG SMTP: Found extension "ETRN", arg "" 22 Dec 2009 15:13:21,384 INFO root:197 - DEBUG SMTP: Found extension "ATRN", arg "" 22 Dec 2009 15:13:21,384 INFO root:197 - DEBUG SMTP: Found extension "DSN", arg "" 22 Dec 2009 15:13:21,385 INFO root:197 - DEBUG SMTP: Found extension "CHECKPOINT", arg "" 22 Dec 2009 15:13:21,385 INFO root:197 - DEBUG SMTP: Found extension "8BITMIME", arg "" 22 Dec 2009 15:13:21,385 INFO root:197 - DEBUG SMTP: Found extension "AUTH", arg "CRAM-MD5 DIGEST-MD5 LOGIN PLAIN" 22 Dec 2009 15:13:21,385 INFO root:197 - DEBUG SMTP: Found extension "AUTH=LOGIN", arg "" 22 Dec 2009 15:13:21,386 INFO root:197 - DEBUG SMTP: Found extension "STARTTLS", arg "" 22 Dec 2009 15:13:21,386 INFO root:197 - DEBUG SMTP: Found extension "HELP", arg "" 22 Dec 2009 15:13:21,389 INFO root:197 - STARTTLS 22 Dec 2009 15:13:21,430 INFO root:197 - 220 2.0.0 Ready to start TLS 22 Dec 2009 15:13:21,809 INFO root:197 - EHLO fsb160 22 Dec 2009 15:13:21,886 WARN E:314 - Failed to send email javax.mail.MessagingException: Can't send command to SMTP host; 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.sendCommand(SMTPTransport.java:1420) at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:1408) at com.sun.mail.smtp.SMTPTransport.ehlo(SMTPTransport.java:847) at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:384) at javax.mail.Service.connect(Service.java:275) at javax.mail.Service.connect(Service.java:156) at java.lang.Thread.run(Unknown Source) 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 com.sun.net.ssl.internal.ssl.Alerts.getSSLException(Unknown Source) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.fatal(Unknown Source) at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Unknown Source) at com.sun.net.ssl.internal.ssl.Handshaker.fatalSE(Unknown Source) at com.sun.net.ssl.internal.ssl.ClientHandshaker.serverCertificate(Unknown Source) at com.sun.net.ssl.internal.ssl.ClientHandshaker.processMessage(Unknown Source) at com.sun.net.ssl.internal.ssl.Handshaker.processLoop(Unknown Source) at com.sun.net.ssl.internal.ssl.Handshaker.process_record(Unknown Source) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.readRecord(Unknown Source) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.performInitialHandshake(Unknown Source) at com.sun.net.ssl.internal.ssl.SSLSocketImpl.writeRecord(Unknown Source) at com.sun.net.ssl.internal.ssl.AppOutputStream.write(Unknown Source) at com.sun.mail.util.TraceOutputStream.write(TraceOutputStream.java:101) at java.io.BufferedOutputStream.flushBuffer(Unknown Source) at java.io.BufferedOutputStream.flush(Unknown Source) at com.sun.mail.smtp.SMTPTransport.sendCommand(SMTPTransport.java:1418) ... 7 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(Unknown Source) at sun.security.validator.PKIXValidator.engineValidate(Unknown Source) at sun.security.validator.Validator.validate(Unknown Source) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.validate(Unknown Source) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source) at com.sun.net.ssl.internal.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source) ... 19 more Caused by: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target at sun.security.provider.certpath.SunCertPathBuilder.engineBuild(Unknown Source) at java.security.cert.CertPathBuilder.build(Unknown Source) ... 25 more
The code used to create the session and to connect to the server:
Session session = EmailUtilities.createSession(smtpServer, smtpPort, smtpSSL, smtpAuthentication); Transport transport = session.getTransport(); transport.connect(smtpServer, smtpUser, smtpPassword); try { MimeMessage message = EmailUtilities.createMessage(Main.APPLICATION_NAME + " " + Main.APPLICATION_VERSION, session, to, from, subject, body, attachmentName, attachment, "application/pdf"); transport.sendMessage(message, message.getAllRecipients()); } catch (Exception e) { throw new Exception(e); } finally { transport.close(); } public static Session createSession(String smtpServer, Integer smtpPort, boolean ssl, boolean authenticate) { String protocol = "smtp"; //$NON-NLS-1$ if (ssl) { protocol = "smtps"; //$NON-NLS-1$ } // -- Attaching to default Session, or we could start a new one -- Properties props = new Properties(); props.put("mail.transport.protocol", protocol); props.put("mail." + protocol + ".host", smtpServer); props.put("mail." + protocol + ".port", smtpPort.toString()); props.put("mail." + protocol + ".starttls.enable", Boolean.TRUE.toString()); if (authenticate) { props.put("mail." + protocol + ".auth", Boolean.TRUE.toString()); } Session session = Session.getDefaultInstance(props, null); session.setDebug(true); return session; }