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Using JavaMail with a Self Signed Certificate

Tags:

java

ssl

self-signed

jakarta-mail

I have a servlet that contains the following code:

System.setProperty("javax.net.ssl.keyStore", getServletContext().getRealPath("keystore.jks"));
System.setProperty("javax.net.ssl.keyStorePassword", "123456");
System.setProperty("javax.net.ssl.trustStore",getServletContext().getRealPath("keystore.jks"));
System.setProperty("javax.net.ssl.trustStorePassword","123456");

SSLSocketFactory sslsocketfactory = (SSLSocketFactory) SSLSocketFactory.getDefault();
SSLSocket sslsocket = (SSLSocket) sslsocketfactory.createSocket("127.0.0.1", 606);

With this code I'm able to use SSL (what is mandatory for my case). Later in the same servlet I need to send an e-mail using JavaMail. When I try to send this e-mail without using my certificate in the other code, it works fine, but when I try using it the following message is returned: Using port 465 ->

DEBUG: setDebug: JavaMail version 1.4.7
DEBUG: setDebug: JavaMail version 1.4.7
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 465, isSSL false

Aaand get stuck on this =p.

Using port 587 ->

DEBUG: setDebug: JavaMail version 1.4.7
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth true
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 g66sm55412571yhd.11 - gsmtp
DEBUG SMTP: connected to host "smtp.gmail.com", port: 587

EHLO RAI-PC
250-mx.google.com at your service, [201.82.118.174]
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 ""
DEBUG SMTP: use8bit false
MAIL FROM:<[email protected]>
530 5.7.0 Must issue a STARTTLS command first. g66sm55412571yhd.11 - gsmtp
DEBUG SMTP: got response code 530, with response: 530 5.7.0 Must issue a STARTTLS command first. g66sm55412571yhd.11 - gsmtp

RSET
250 2.1.5 Flushed g66sm55412571yhd.11 - gsmtp
DEBUG SMTP: MessagingException while sending, THROW: 
com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. g66sm55412571yhd.11 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2108)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1609)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1117)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)
    at servlet.Main.service(Main.java:221)
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:728)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:305)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210)
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:222)
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:123)
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:472)
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:171)
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:99)
    at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:953)
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118)
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:408)
    at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1023)
    at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:589)
    at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:310)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
    at java.lang.Thread.run(Unknown Source)
QUIT
221 2.0.0 closing connection g66sm55412571yhd.11 - gsmtp
Jul 10, 2013 7:04:40 PM org.apache.catalina.core.StandardWrapperValve invoke
SEVERE: Servlet.service() for servlet [servletMain] in context with path [/servicotcc] threw exception
java.lang.RuntimeException: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. g66sm55412571yhd.11 - gsmtp

    at servlet.Main.service(Main.java:226)
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:728)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:305)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210)
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:222)
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:123)
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:472)
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:171)
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:99)
    at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:953)
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118)
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:408)
    at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1023)
    at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:589)
    at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:310)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
    at java.lang.Thread.run(Unknown Source)
Caused by: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.0 Must issue a STARTTLS command first. g66sm55412571yhd.11 - gsmtp

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(SMTPTransport.java:2108)
    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTransport.java:1609)
    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTransport.java:1117)
    at javax.mail.Transport.send0(Transport.java:195)
    at javax.mail.Transport.send(Transport.java:124)
    at servlet.Main.service(Main.java:221)
    ... 17 more

The Properties code:

Properties props = new Properties();
props.put("mail.smtp.host", "smtp.gmail.com");
props.put("mail.smtp.socketFactory.port", "465");
props.put("mail.smtp.socketFactory.class", "javax.net.ssl.SSLSocketFactory");
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.port", "465");

I can't send the e-mail like this (I'm not sure what is the exactly cause). What should I do?

-- EDIT --

After importing the google SMTP certificate to my keystore and changing the port and properties to:

Properties props = new Properties(); 
props.put("mail.smtp.host", "smtp.gmail.com");
props.put("mail.smtp.socketFactory.port", "465");
props.put("mail.smtp.socketFactory.class", sslsocketfactory);
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.port", "465");
props.put("mail.smtp.ssl.enable", "true");
props.put("mail.smtp.starttls.enable", "true");

My output changed to:

DEBUG: setDebug: JavaMail version 1.4.7
DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Oracle]
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: useEhlo true, useAuth true
DEBUG SMTP: trying to connect to host "smtp.gmail.com", port 465, isSSL true
Jul 10, 2013 8:26:46 PM org.apache.catalina.core.StandardWrapperValve invoke
SEVERE: Servlet.service() for servlet [servletMain] in context with path [/servicotcc] threw exception
java.lang.RuntimeException: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 465;
  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 servlet.Main.service(Main.java:229)
    at javax.servlet.http.HttpServlet.service(HttpServlet.java:728)
    at org.apache.catalina.core.ApplicationFilterChain.internalDoFilter(ApplicationFilterChain.java:305)
    at org.apache.catalina.core.ApplicationFilterChain.doFilter(ApplicationFilterChain.java:210)
    at org.apache.catalina.core.StandardWrapperValve.invoke(StandardWrapperValve.java:222)
    at org.apache.catalina.core.StandardContextValve.invoke(StandardContextValve.java:123)
    at org.apache.catalina.authenticator.AuthenticatorBase.invoke(AuthenticatorBase.java:472)
    at org.apache.catalina.core.StandardHostValve.invoke(StandardHostValve.java:171)
    at org.apache.catalina.valves.ErrorReportValve.invoke(ErrorReportValve.java:99)
    at org.apache.catalina.valves.AccessLogValve.invoke(AccessLogValve.java:953)
    at org.apache.catalina.core.StandardEngineValve.invoke(StandardEngineValve.java:118)
    at org.apache.catalina.connector.CoyoteAdapter.service(CoyoteAdapter.java:408)
    at org.apache.coyote.http11.AbstractHttp11Processor.process(AbstractHttp11Processor.java:1023)
    at org.apache.coyote.AbstractProtocol$AbstractConnectionHandler.process(AbstractProtocol.java:589)
    at org.apache.tomcat.util.net.JIoEndpoint$SocketProcessor.run(JIoEndpoint.java:310)
    at java.util.concurrent.ThreadPoolExecutor.runWorker(Unknown Source)
    at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)
    at java.lang.Thread.run(Unknown Source)
Caused by: javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 465;
  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.openServer(SMTPTransport.java:1961)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:654)
    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 javax.mail.Transport.send0(Transport.java:194)
    at javax.mail.Transport.send(Transport.java:124)
    at servlet.Main.service(Main.java:224)
    ... 17 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(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.fatal(Unknown Source)
    at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
    at sun.security.ssl.Handshaker.fatalSE(Unknown Source)
    at sun.security.ssl.ClientHandshaker.serverCertificate(Unknown Source)
    at sun.security.ssl.ClientHandshaker.processMessage(Unknown Source)
    at sun.security.ssl.Handshaker.processLoop(Unknown Source)
    at sun.security.ssl.Handshaker.process_record(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.readRecord(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.performInitialHandshake(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at sun.security.ssl.SSLSocketImpl.startHandshake(Unknown Source)
    at com.sun.mail.util.SocketFetcher.configureSSLSocket(SocketFetcher.java:549)
    at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:354)
    at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:237)
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1927)
    ... 24 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 sun.security.ssl.X509TrustManagerImpl.validate(Unknown Source)
    at sun.security.ssl.X509TrustManagerImpl.checkTrusted(Unknown Source)
    at sun.security.ssl.X509TrustManagerImpl.checkServerTrusted(Unknown Source)
    ... 36 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)
    ... 42 more
like image 880
Raí Avancini Avatar asked Jul 10 '13 21:07

Raí Avancini

2 Answers

Get rid of the socket factory stuff:

Setting various socketFactory properties. Long, long ago JavaMail didn't have built in support for SSL connections, so it was necessary to set these properties to use SSL. This hasn't been the case for years; remove these properties and simplify your code. The easiest way to enable SSL support in current versions of JavaMail is to set the property "mail.smtp.ssl.enable" to "true". (Replace "smtp" with "imap" or "pop3" as appropriate.)

See these Gmail examples.

The Gmail certificate needs to be in your trust store, not your key store.

like image 103
Bill Shannon Avatar answered Oct 22 '22 20:10

Bill Shannon

Solution - change properties to:

 Properties props = new Properties();
 props.put("mail.smtp.host", "smtp.gmail.com");
 props.put("mail.smtp.socketFactory.port", "587");
 props.put("mail.smtp.socketFactory.class", "javax.net.SocketFactory");
 props.put("mail.smtp.auth", "true");
 props.put("mail.smtp.port", "587");
 props.put("mail.smtp.ssl.enable", "false");
 props.put("mail.smtp.starttls.enable", "true");
 props.put("mail.smtp.ssl.trust", "smtp.gmail.com");
like image 38
Raí Avancini Avatar answered Oct 22 '22 20:10

Raí Avancini
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