SMTP port 25 sounds like a non-SSL connection but your Graylog2 setup
is trying to use SSL. "javax.net.ssl.SSLException: Unrecognized SSL
message, plaintext connection?"

Disable SMTP SSL in your graylog2-server.conf: transport_email_use_ssl = false

That is part of the shipped example config file.

On Mon, Mar 10, 2014 at 3:31 PM, 2p3rf3ct <[email protected]> wrote:
>
> Using Graylog Server 0.20.1 and the equivalent web interface I'm having
> problems sending alert messages for streams. Using the 'Send Test Alert'
> message results in a 500 error on the server. I have tried a using localhost
> port 25 and a TLS enabled server - the former works from the command line
> fine. This is running on an Amazon EC2 instance. Any ideas anyone?
>
> 2014-03-10 13:51:35,393 DEBUG: org.graylog2.rest.accesslog - 10.73.184.245 -
> [Mon Mar 10 13:51:35 GMT 2014] "GET /system/cluster/nodes"
> graylog2-web/0.20.1 200 -1
> 2014-03-10 13:51:35,493 DEBUG: org.graylog2.inputs.syslog.SyslogProcessor -
> Adding received syslog message <18548750-a85b-11e3-9a00-22000a49b8f5> to
> process buffer: source: gryweb-grayweb-i-af3811ee | message:
> gryweb-grayweb-i-af3811ee sendmail[25015]: s2ADpZt9025015: localhost
> [127.0.0.1] did not issue MAIL/EXPN/VRFY/ETRN during connection to MTA
> 2014-03-10 13:51:35,518 DEBUG:
> org.graylog2.buffers.processors.ProcessBufferProcessor - Starting to process
> message <18548750-a85b-11e3-9a00-22000a49b8f5>.
> 2014-03-10 13:51:35,518 DEBUG:
> org.graylog2.buffers.processors.ProcessBufferProcessor - Applying filter
> [Static field appender] on message <18548750-a85b-11e3-9a00-22000a49b8f5>.
> 2014-03-10 13:51:35,518 DEBUG:
> org.graylog2.buffers.processors.ProcessBufferProcessor - Applying filter
> [Extractor] on message <18548750-a85b-11e3-9a00-22000a49b8f5>.
> 2014-03-10 13:51:35,518 DEBUG:
> org.graylog2.buffers.processors.ProcessBufferProcessor - Applying filter
> [Blacklister] on message <18548750-a85b-11e3-9a00-22000a49b8f5>.
> 2014-03-10 13:51:35,523 ERROR:
> org.graylog2.rest.resources.streams.alerts.StreamAlertResource - Sending
> dummy alert failed: {}
> org.apache.commons.mail.EmailException: Sending the email to the following
> server failed : localhost:25
>         at org.apache.commons.mail.Email.sendMimeMessage(Email.java:1410)
>         at org.apache.commons.mail.Email.send(Email.java:1437)
>         at org.graylog2.alerts.AlertSender.sendEmail(AlertSender.java:106)
>         at org.graylog2.alerts.AlertSender.sendEmails(AlertSender.java:73)
>         at
> org.graylog2.rest.resources.streams.alerts.StreamAlertResource.sendDummyAlert(StreamAlertResource.java:355)
>         at sun.reflect.NativeMethodAccessorImpl.invoke0(Native Method)
>         at
> sun.reflect.NativeMethodAccessorImpl.invoke(NativeMethodAccessorImpl.java:57)
>         at
> sun.reflect.DelegatingMethodAccessorImpl.invoke(DelegatingMethodAccessorImpl.java:43)
>         at java.lang.reflect.Method.invoke(Method.java:606)
>         at
> org.glassfish.jersey.server.model.internal.ResourceMethodInvocationHandlerFactory$1.invoke(ResourceMethodInvocationHandlerFactory.java:81)
>         at
> org.glassfish.jersey.server.model.internal.AbstractJavaResourceMethodDispatcher$1.run(AbstractJavaResourceMethodDispatcher.java:151)
>         at
> org.glassfish.jersey.server.model.internal.AbstractJavaResourceMethodDispatcher.invoke(AbstractJavaResourceMethodDispatcher.java:171)
>         at
> org.glassfish.jersey.server.model.internal.JavaResourceMethodDispatcherProvider$ResponseOutInvoker.doDispatch(JavaResourceMethodDispatcherProvider.java:152)
>         at
> org.glassfish.jersey.server.model.internal.AbstractJavaResourceMethodDispatcher.dispatch(AbstractJavaResourceMethodDispatcher.java:104)
>         at
> org.glassfish.jersey.server.model.ResourceMethodInvoker.invoke(ResourceMethodInvoker.java:402)
>         at
> org.glassfish.jersey.server.model.ResourceMethodInvoker.apply(ResourceMethodInvoker.java:349)
>         at
> org.glassfish.jersey.server.model.ResourceMethodInvoker.apply(ResourceMethodInvoker.java:106)
>         at
> org.glassfish.jersey.server.ServerRuntime$1.run(ServerRuntime.java:259)
>         at org.glassfish.jersey.internal.Errors$1.call(Errors.java:271)
>         at org.glassfish.jersey.internal.Errors$1.call(Errors.java:267)
>         at org.glassfish.jersey.internal.Errors.process(Errors.java:315)
>         at org.glassfish.jersey.internal.Errors.process(Errors.java:297)
>         at org.glassfish.jersey.internal.Errors.process(Errors.java:267)
>         at
> org.glassfish.jersey.process.internal.RequestScope.runInScope(RequestScope.java:318)
>         at
> org.glassfish.jersey.server.ServerRuntime.process(ServerRuntime.java:236)
>         at
> org.glassfish.jersey.server.ApplicationHandler.handle(ApplicationHandler.java:1010)
>         at
> org.graylog2.jersey.container.netty.NettyContainer.messageReceived(NettyContainer.java:275)
>         at
> org.jboss.netty.channel.SimpleChannelUpstreamHandler.handleUpstream(SimpleChannelUpstreamHandler.java:70)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:564)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline$DefaultChannelHandlerContext.sendUpstream(DefaultChannelPipeline.java:791)
>         at
> org.jboss.netty.handler.stream.ChunkedWriteHandler.handleUpstream(ChunkedWriteHandler.java:142)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:564)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline$DefaultChannelHandlerContext.sendUpstream(DefaultChannelPipeline.java:791)
>         at
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:296)
>         at
> org.jboss.netty.handler.codec.frame.FrameDecoder.unfoldAndFireMessageReceived(FrameDecoder.java:459)
>         at
> org.jboss.netty.handler.codec.replay.ReplayingDecoder.callDecode(ReplayingDecoder.java:536)
>         at
> org.jboss.netty.handler.codec.replay.ReplayingDecoder.messageReceived(ReplayingDecoder.java:435)
>         at
> org.jboss.netty.channel.SimpleChannelUpstreamHandler.handleUpstream(SimpleChannelUpstreamHandler.java:70)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:564)
>         at
> org.jboss.netty.channel.DefaultChannelPipeline.sendUpstream(DefaultChannelPipeline.java:559)
>         at
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:268)
>         at
> org.jboss.netty.channel.Channels.fireMessageReceived(Channels.java:255)
>         at
> org.jboss.netty.channel.socket.nio.NioWorker.read(NioWorker.java:88)
>         at
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.process(AbstractNioWorker.java:108)
>         at
> org.jboss.netty.channel.socket.nio.AbstractNioSelector.run(AbstractNioSelector.java:318)
>         at
> org.jboss.netty.channel.socket.nio.AbstractNioWorker.run(AbstractNioWorker.java:89)
>         at
> org.jboss.netty.channel.socket.nio.NioWorker.run(NioWorker.java:178)
>         at
> org.jboss.netty.util.ThreadRenamingRunnable.run(ThreadRenamingRunnable.java:108)
>         at
> org.jboss.netty.util.internal.DeadLockProofWorker$1.run(DeadLockProofWorker.java:42)
>         at
> java.util.concurrent.ThreadPoolExecutor.runWorker(ThreadPoolExecutor.java:1145)
>         at
> java.util.concurrent.ThreadPoolExecutor$Worker.run(ThreadPoolExecutor.java:615)
>         at java.lang.Thread.run(Thread.java:724)
> Caused by: javax.mail.MessagingException: Could not connect to SMTP host:
> localhost, port: 25;
>   nested exception is:
>         javax.net.ssl.SSLException: Unrecognized SSL message, plaintext
> connection?
>         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: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:1400)
>         ... 51 more
> Caused by: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext
> connection?
>         at
> sun.security.ssl.InputRecord.handleUnknownRecord(InputRecord.java:671)
>         at sun.security.ssl.InputRecord.read(InputRecord.java:504)
>
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