SMTP with TLS on port 587

[brunoschwartz]

Dear All,
I have a little problem with email setup. I have to use external smtp server from my company to send emails. I was working OK but suddenly it stopped after they did some changes on the smtp server side. The advice I am getting is to connect to smtp server on port 587 and ask my mail client to initiate STARTTLS. When I set it up like this in thunderbird it works fine. However in OX when setting the port 587 it automatically reverts to SSL, which the smtp server does not support. I read in other post that when using port 25, the ox will start tls automatically when detected the support of it on the smtp server side. However, how can I inactivate ssl and turn on tls on the port 587.

PS: I have two mail accounts, one is localhost through ox and one more external imap account with the external smtp as I explained above.

Here is piece of my log with I try to connect on 587 port:

13-Feb-2011 14:42:19 com.openexchange.ajax.Mail action
SEVERE: MSG-1030 Category=3 Message=Wrong or missing login data to access mail transport server xxx.xxx.xxx.xxx. Error message from mail transport server: failed to connect exceptionID=-396147876-47159
MSG-1030 Category=3 Message=Wrong or missing login data to access mail transport server xxx.xxx.xxx.xxx. Error message from mail transport server: failed to connect exceptionID=-396147876-47159
at com.openexchange.smtp.SMTPTransport.sendMailMessag e(SMTPTransport.java:549)
at com.openexchange.mail.transport.MailTransport.send MailMessage(MailTransport.java:155)
at com.openexchange.mail.MailServletInterfaceImpl.sen dMessage(MailServletInterfaceImpl.java:1890)
at com.openexchange.ajax.Mail.action(Mail.java:4191)
at com.openexchange.ajax.AJAXServlet.fireUploadEvent( AJAXServlet.java:788)
at com.openexchange.ajax.Mail.doPost(Mail.java:4063)
at javax.servlet.http.HttpServlet.service(HttpServlet .java:616)
at com.openexchange.ajax.AJAXServlet.service(AJAXServ let.java:392)
at com.openexchange.ajax.SessionServlet.service(Sessi onServlet.java:182)
at com.openexchange.ajax.PermissionServlet.service(Pe rmissionServlet.java:66)
at javax.servlet.http.HttpServlet.service(HttpServlet .java:689)
at com.openexchange.ajp13.najp.AJPv13RequestHandlerIm pl.doServletService(AJPv13RequestHandlerImpl.java: 504)
at com.openexchange.ajp13.AJPv13Request.response(AJPv 13Request.java:129)
at com.openexchange.ajp13.najp.AJPv13RequestHandlerIm pl.createResponse(AJPv13RequestHandlerImpl.java:31 6)
at com.openexchange.ajp13.najp.AJPv13ConnectionImpl.c reateResponse(AJPv13ConnectionImpl.java:207)
at com.openexchange.ajp13.najp.AJPv13Task.call(AJPv13 Task.java:346)
at java.util.concurrent.FutureTask$Sync.innerRun(Futu reTask.java:303)
at java.util.concurrent.FutureTask.run(FutureTask.jav a:138)
at com.openexchange.threadpool.internal.CustomThreadP oolExecutor$Worker.runTask(CustomThreadPoolExecuto r.java:738)
at com.openexchange.threadpool.internal.CustomThreadP oolExecutor$Worker.run(CustomThreadPoolExecutor.ja va:764)
at java.lang.Thread.run(Thread.java:662)
Caused by: javax.mail.AuthenticationFailedException: failed to connect
at javax.mail.Service.connect(Service.java:322)
at com.openexchange.smtp.SMTPTransport.sendMailMessag e(SMTPTransport.java:544)
... 20 more

[Martin Heiland]

Hi,

Port 587/tcp is specified for Message Submission (RFC4409). SMTP with STARTTLS is used on Port 25/tcp exclusively and is the current standard for secure mail transfer. STARTTLS via Port 587 is non-standard usage. However, you might check if the SMTP Server announces STARTTLS capability in response to a HELO command.

Greetings

[Carsten Hoeger]

Nevertheless, RFC 4409 explicitly allows STARTTLS extension.
Please file a bug report, if Open-Xchange does not support that.

http://tools.ietf.org/html/rfc4409#section-7

[brunoschwartz]

Martin, Carsten, thank you for your replies.The external smtp server works with starttls on port 587. How can I check or set the ox to accept the tls on that port? As I said, when used with thunderbird, it works flawlessly. Cheers,

[Martin Heiland]

Hi,

perhaps Thunderbird just does trial and error. You could check for STARTTLS capability on Port 587 like this:

[mbraun@mbraun ~]$ telnet xxx.open-xchange.com 587
Trying xxx.xxx.xxx.xxx...
Connected to xxx.open-xchange.com.
Escape character is '^]'.
220 xxx.open-xchange.com ESMTP Postfix
EHLO mbraun
250-xxx.open-xchange.com
250-PIPELINING
250-SIZE 100971520
250-VRFY
250-ETRN
[b]250-STARTTLS[/b]
250-AUTH LOGIN PLAIN
250-AUTH=LOGIN PLAIN
250-ENHANCEDSTATUSCODES
250-8BITMIME
250 DSN

If you server also announces STARTTLS support, a bug report would be the way to go.

Thanks!

[Carsten Hoeger]

Yes, as Martin states, the smtp server listening on port 587 MUST of course announce, that it supports STARTTLS!

[brunoschwartz]

Martin and Carsten,

Thanks for the reply. I tested the server before and it does announce starttls. Here is the log:

MacBook-2:~ bs$ telnet xxx.xxx.xxx.xxx 587
Trying xxx.xxx.xxx.xxx...
Connected to xxx.xxx.xxx.xxx.
Escape character is '^]'.
220 xxx.xxx.xxx.xxx 4.73 Wed, 16 Feb 2011 23:08:08 +0000
EHLO xxx
250-xxx.xxx.xxx.xxx Hello xxx.xxx.xxx.xxx [xxx.xxx.xxx.xxx]
250-SIZE 52428800
250-PIPELINING
250-AUTH PLAIN LOGIN
250-STARTTLS
250 HELP


Would that be a bug in OX then?

[Carsten Hoeger]

Yes, this is clearly a bug.

[brunoschwartz]

Hello Carsten,

What do I do then? I am a mere user and do not know how to submit a bug :-)

Regards

[Carsten Hoeger]

Just visit https://bugs.open-xchange.com/ and there you can create an account. Once you've done that, you're able to submit a bug.