SSL with javamail not working

Question

Trying to connect to gmail with TSL, I am stuck on some error msgs. Given below code:

import java.util.*;
import java.util.logging.*;
import javax.mail.*;
import javax.mail.internet.*;

public class MailHandler extends Handler {
    public void publish(LogRecord record) {
    try {
        String host = "smtp.gmail.com";
        int port = 587;
        String username = "[email protected]";
        String password = "cookiepassword";

        Properties props = new Properties();
        props.put("mail.smtp.auth", "true");
        props.put("mail.smtp.starttls.enable", "true");
        //props.setProperty("mail.smtp.ssl.trust", "smtpserver");
        props.put("mail.debug", "true");

        Session session = Session.getInstance(props);

        Message message = new MimeMessage(session);
        message.setFrom(new InternetAddress("[email protected]"));
        message.setRecipients(Message.RecipientType.TO,InternetAddress.parse("[email protected]"));
        message.setSubject(record.getMessage());
        message.setText("Auto");

        Transport transport = session.getTransport("smtp");
        transport.connect(host, port, username, password);

        Transport.send(message);
    } catch (MessagingException ex) {
        Logger.getLogger(MailHandler.class.getName()).log(Level.SEVERE, null, ex);
    }
  }
    @Override
    public void close() {}
    @Override
    public void flush() {}
}

I get

run:
DEBUG: JavaMail version 1.4.4
DEBUG: successfully loaded resource: /META-INF/javamail.default.providers
DEBUG: Tables of loaded providers
DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], com.sun.mail.smtp.SMTPTransport=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc], com.sun.mail.imap.IMAPSSLStore=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3SSLStore=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], com.sun.mail.imap.IMAPStore=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3Store=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc]}
DEBUG: Providers Listed By Protocol: {imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], imap=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], smtps=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], pop3=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc], pop3s=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], smtp=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]}
DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP b5sm13118062wbh.4
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO FloWorkLinux
250-mx.google.com at your service, [95.146.161.196]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
09-Dec-2011 17:05:32 smsalertor.MailHandler publish
SEVERE: null
javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    java.net.SocketException: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.DefaultSSLContextImpl)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1880)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:648)
    at javax.mail.Service.connect(Service.java:295)
    at smsalertor.MailHandler.publish(MailHandler.java:33)
    at smsalertor.SMSAlertor.main(SMSAlertor.java:107)
Caused by: java.net.SocketException: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.DefaultSSLContextImpl)
    at javax.net.ssl.DefaultSSLSocketFactory.throwException(SSLSocketFactory.java:196)
    at javax.net.ssl.DefaultSSLSocketFactory.createSocket(SSLSocketFactory.java:216)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:432)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1875)
    ... 4 more
Caused by: java.security.NoSuchAlgorithmException: Error constructing implementation (algorithm: Default, provider: SunJSSE, class: sun.security.ssl.DefaultSSLContextImpl)
    at java.security.Provider$Service.newInstance(Provider.java:1262)
    at sun.security.jca.GetInstance.getInstance(GetInstance.java:236)
    at sun.security.jca.GetInstance.getInstance(GetInstance.java:164)
    at javax.net.ssl.SSLContext.getInstance(SSLContext.java:142)
    at javax.net.ssl.SSLContext.getDefault(SSLContext.java:85)
    at javax.net.ssl.SSLSocketFactory.getDefault(SSLSocketFactory.java:119)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:427)
    ... 5 more
Caused by: java.io.EOFException
    at java.io.DataInputStream.readInt(DataInputStream.java:392)
    at sun.security.provider.JavaKeyStore.engineLoad(JavaKeyStore.java:645)
    at sun.security.provider.JavaKeyStore$JKS.engineLoad(JavaKeyStore.java:55)
    at java.security.KeyStore.load(KeyStore.java:1201)
    at sun.security.ssl.TrustManagerFactoryImpl.getCacertsKeyStore(TrustManagerFactoryImpl.java:221)
    at sun.security.ssl.DefaultSSLContextImpl.getDefaultTrustManager(DefaultSSLContextImpl.java:87)
    at sun.security.ssl.DefaultSSLContextImpl.<init>(DefaultSSLContextImpl.java:57)
    at sun.reflect.NativeConstructorAccessorImpl.newInstance0(Native Method)
    at sun.reflect.NativeConstructorAccessorImpl.newInstance(NativeConstructorAccessorImpl.java:57)
    at sun.reflect.DelegatingConstructorAccessorImpl.newInstance(DelegatingConstructorAccessorImpl.java:45)
    at java.lang.reflect.Constructor.newInstance(Constructor.java:532)
    at java.lang.Class.newInstance0(Class.java:372)
    at java.lang.Class.newInstance(Class.java:325)
    at java.security.Provider$Service.newInstance(Provider.java:1238)
    ... 11 more
BUILD SUCCESSFUL (total time: 10 seconds)

Uncommenting props.setProperty("mail.smtp.ssl.trust", "smtpserver"); changes this to

run:
DEBUG: JavaMail version 1.4.4
DEBUG: successfully loaded resource: /META-INF/javamail.default.providers
DEBUG: Tables of loaded providers
DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], com.sun.mail.smtp.SMTPTransport=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc], com.sun.mail.imap.IMAPSSLStore=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3SSLStore=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], com.sun.mail.imap.IMAPStore=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], com.sun.mail.pop3.POP3Store=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc]}
DEBUG: Providers Listed By Protocol: {imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], imap=javax.mail.Provider[STORE,imap,com.sun.mail.imap.IMAPStore,Sun Microsystems, Inc], smtps=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport,Sun Microsystems, Inc], pop3=javax.mail.Provider[STORE,pop3,com.sun.mail.pop3.POP3Store,Sun Microsystems, Inc], pop3s=javax.mail.Provider[STORE,pop3s,com.sun.mail.pop3.POP3SSLStore,Sun Microsystems, Inc], smtp=javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]}
DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 587, isSSL false
220 mx.google.com ESMTP em4sm13086182wbb.20
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO FloWorkLinux
250-mx.google.com at your service, [95.146.161.196]
250-SIZE 35882577
250-8BITMIME
250-STARTTLS
250 ENHANCEDSTATUSCODES
DEBUG SMTP: Found extension "SIZE", arg "35882577"
DEBUG SMTP: Found extension "8BITMIME", arg ""
DEBUG SMTP: Found extension "STARTTLS", arg ""
DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""
STARTTLS
220 2.0.0 Ready to start TLS
09-Dec-2011 17:09:37 smsalertor.MailHandler publish
SEVERE: null
javax.mail.MessagingException: Could not convert socket to TLS;
  nested exception is:
    java.io.IOException: Can't create MailSSLSocketFactory
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1880)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:648)
    at javax.mail.Service.connect(Service.java:295)
    at smsalertor.MailHandler.publish(MailHandler.java:33)
    at smsalertor.SMSAlertor.main(SMSAlertor.java:107)
Caused by: java.io.IOException: Can't create MailSSLSocketFactory
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:421)
    at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTransport.java:1875)
    ... 4 more
Caused by: java.security.KeyStoreException: problem accessing trust storejava.io.EOFException
    at sun.security.ssl.TrustManagerFactoryImpl.engineInit(TrustManagerFactoryImpl.java:75)
    at javax.net.ssl.TrustManagerFactory.init(TrustManagerFactory.java:247)
    at com.sun.mail.util.MailSSLSocketFactory$MailTrustManager.<init>(MailSSLSocketFactory.java:333)
    at com.sun.mail.util.MailSSLSocketFactory$MailTrustManager.<init>(MailSSLSocketFactory.java:323)
    at com.sun.mail.util.MailSSLSocketFactory.<init>(MailSSLSocketFactory.java:115)
    at com.sun.mail.util.MailSSLSocketFactory.<init>(MailSSLSocketFactory.java:94)
    at com.sun.mail.util.SocketFetcher.startTLS(SocketFetcher.java:413)
    ... 5 more
BUILD SUCCESSFUL (total time: 7 seconds)

Anyone seen this before?

Edit:

Talk about turning a 10 minute copy paste tutorial into a full day head ache. I still haven't solved this, however, I have been reading more and more. Apparently, I need a store of public ssl signatures to compare against. This are supposed to be in a path along the lines of /usr/lib/jvm/java-6-sun-1.6.0.26/jre/lib/security. Using sudo update-alternatives --config java I am pointing this at /usr/lib/jvm/java-6-sun/jre/bin/java which in turn points at that folder, however, there exists also a /usr/lib/jvm/default-java symlink unaffected by this, currently pointing to java-6-openjdk, and if I look into that folder, it was missing security certificates. And just that is being used by NetBeans. Oh joy.

Following this recommendation, I did sudo apt-get install libbcprov-java which gave me my security folder in the openjdk (after mucking about with the sun-jdk for a while, which presumably now is installed, but who knows where, since it isn't showing up in /usr/lib/jvm/).

This still produces the same error msg. Hence I moved it all over to Windows, tried to compile, turns out above code isn't quite working (doesn't matter for our purpose as the non working bits come after the SSL bit) (hey and thanks for all the incorrect tutorials out there by now, what a mess). Anyway, finally got something working with this solution (although there is a fair amount of redundancy in there, and although it is not TLS but SSL, but hey, ...). In any case, all working fine and smooth, so back to Ubuntu, and ding dong, same error message as above again. Clearly looks like a problem surrounding the KeyStore. I am still at a loss as to how to fix it (current error is the first one mentioned above).

Answer 1

It took days to try hundreds of ideas according to keytool, truststore, cacerst etc. But finally I had to simply set the mail.smtp.ssl.trust property:

props.setProperty("mail.smtp.ssl.trust", "smtpserver");