I am unable to connect to a SMTP host using the E-mail Notification abilities in Jenkins. I believe I have everything set up correctly. This is my configuration:

SMTP Server: smtp.gmail.com
Default user e-mail suffix: @gmail.com
Use SMTP Authentication: checked
User Name: myUsername@gmail.com
Password: myGmailPassword
Use SSL: checked
SMTP Port: 465
Reply-To Address: NOREPLY@gmail.com
Charset: UTF-8

This is the error I am running into:

Failed to send out e-mail
javax.mail.MessagingException: Could not connect to SMTP host: smtp.gmail.com, port: 465;
nested exception is:
java.net.ConnectException: Connection timed out: connect

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1934)

at com.sun.mail.smtp.SMTPTransport.protocolConnect(SMTPTransport.java:638)

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 hudson.tasks.Mailer$DescriptorImpl.doSendTestMail(Mailer.java:522)

at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)

at sun.reflect.NativeMethodAccessorImpl.invoke(Unknown Source)

at sun.reflect.DelegatingMethodAccessorImpl.invoke(Unknown Source)

at java.lang.reflect.Method.invoke(Unknown Source)

at org.kohsuke.stapler.Function$InstanceFunction.invoke(Function.java:298)

at org.kohsuke.stapler.Function.bindAndInvoke(Function.java:161)

at org.kohsuke.stapler.Function.bindAndInvokeAndServeResponse(Function.java:96)

at org.kohsuke.stapler.MetaClass$1.doDispatch(MetaClass.java:120)

at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)

at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)

at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)

at org.kohsuke.stapler.MetaClass$6.doDispatch(MetaClass.java:248)

at org.kohsuke.stapler.NameBasedDispatcher.dispatch(NameBasedDispatcher.java:53)

at org.kohsuke.stapler.Stapler.tryInvoke(Stapler.java:728)

at org.kohsuke.stapler.Stapler.invoke(Stapler.java:858)

at org.kohsuke.stapler.Stapler.invoke(Stapler.java:631)

at org.kohsuke.stapler.Stapler.service(Stapler.java:225)

at javax.servlet.http.HttpServlet.service(HttpServlet.java:848)

at org.eclipse.jetty.servlet.ServletHolder.handle(ServletHolder.java:686)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1494)

at hudson.util.PluginServletFilter$1.doFilter(PluginServletFilter.java:96)

at hudson.util.PluginServletFilter.doFilter(PluginServletFilter.java:88)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)

at hudson.security.csrf.CrumbFilter.doFilter(CrumbFilter.java:48)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)

at hudson.security.ChainedServletFilter$1.doFilter(ChainedServletFilter.java:84)

at hudson.security.ChainedServletFilter.doFilter(ChainedServletFilter.java:76)

at hudson.security.HudsonFilter.doFilter(HudsonFilter.java:164)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)

at org.kohsuke.stapler.compression.CompressionFilter.doFilter(CompressionFilter.java:46)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1482)

at hudson.util.CharacterEncodingFilter.doFilter(CharacterEncodingFilter.java:81)

at org.eclipse.jetty.servlet.ServletHandler$CachedChain.doFilter(ServletHandler.java:1474)

at org.eclipse.jetty.servlet.ServletHandler.doHandle(ServletHandler.java:499)

at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:137)

at org.eclipse.jetty.security.SecurityHandler.handle(SecurityHandler.java:533)

at org.eclipse.jetty.server.session.SessionHandler.doHandle(SessionHandler.java:231)

at org.eclipse.jetty.server.handler.ContextHandler.doHandle(ContextHandler.java:1086)

at org.eclipse.jetty.servlet.ServletHandler.doScope(ServletHandler.java:428)

at org.eclipse.jetty.server.session.SessionHandler.doScope(SessionHandler.java:193)

at org.eclipse.jetty.server.handler.ContextHandler.doScope(ContextHandler.java:1020)

at org.eclipse.jetty.server.handler.ScopedHandler.handle(ScopedHandler.java:135)

at org.eclipse.jetty.server.handler.HandlerWrapper.handle(HandlerWrapper.java:116)

at org.eclipse.jetty.server.Server.handle(Server.java:370)

at org.eclipse.jetty.server.AbstractHttpConnection.handleRequest(AbstractHttpConnection.java:489)

at org.eclipse.jetty.server.AbstractHttpConnection.content(AbstractHttpConnection.java:960)

at org.eclipse.jetty.server.AbstractHttpConnection$RequestHandler.content(AbstractHttpConnection.java:1021)

at org.eclipse.jetty.http.HttpParser.parseNext(HttpParser.java:865)

at org.eclipse.jetty.http.HttpParser.parseAvailable(HttpParser.java:240)

at org.eclipse.jetty.server.AsyncHttpConnection.handle(AsyncHttpConnection.java:82)

at org.eclipse.jetty.io.nio.SelectChannelEndPoint.handle(SelectChannelEndPoint.java:668)

at org.eclipse.jetty.io.nio.SelectChannelEndPoint$1.run(SelectChannelEndPoint.java:52)

at winstone.BoundedExecutorService$1.run(BoundedExecutorService.java:77)

at java.util.concurrent.ThreadPoolExecutor$Worker.runTask(Unknown Source)

at java.util.concurrent.ThreadPoolExecutor$Worker.run(Unknown Source)

at java.lang.Thread.run(Unknown Source)

Caused by: java.net.ConnectException: Connection timed out: connect

at java.net.PlainSocketImpl.socketConnect(Native Method)

at java.net.PlainSocketImpl.doConnect(Unknown Source)

at java.net.PlainSocketImpl.connectToAddress(Unknown Source)

at java.net.PlainSocketImpl.connect(Unknown Source)

at java.net.SocksSocketImpl.connect(Unknown Source)

at java.net.Socket.connect(Unknown Source)

at com.sun.net.ssl.internal.ssl.SSLSocketImpl.connect(Unknown Source)

at com.sun.mail.util.SocketFetcher.createSocket(SocketFetcher.java:286)

at com.sun.mail.util.SocketFetcher.getSocket(SocketFetcher.java:205)

at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTransport.java:1900)

... 63 more