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  1. #1

    Default SMTP with TLS on port 587

    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

  2. #2
    Join Date
    Feb 2007
    Location
    Germany
    Posts
    3,695

    Default

    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
    Last edited by Martin Heiland; 02-13-2011 at 11:07 PM.

  3. #3
    Carsten Hoeger is offline Open-Xchange Professional Services
    Join Date
    Mar 2007
    Posts
    703

    Default

    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
    OXpedia.org - the answer to almost all questions.

  4. #4

    Default

    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,

  5. #5
    Join Date
    Feb 2007
    Location
    Germany
    Posts
    3,695

    Default

    Hi,

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

    Code:
    [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
    250-STARTTLS
    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!

  6. #6
    Carsten Hoeger is offline Open-Xchange Professional Services
    Join Date
    Mar 2007
    Posts
    703

    Default

    Yes, as Martin states, the smtp server listening on port 587 MUST of course announce, that it supports STARTTLS!
    OXpedia.org - the answer to almost all questions.

  7. #7

    Default

    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?

  8. #8
    Carsten Hoeger is offline Open-Xchange Professional Services
    Join Date
    Mar 2007
    Posts
    703

    Default

    Yes, this is clearly a bug.
    OXpedia.org - the answer to almost all questions.

  9. #9

    Default

    Hello Carsten,

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

    Regards

  10. #10
    Carsten Hoeger is offline Open-Xchange Professional Services
    Join Date
    Mar 2007
    Posts
    703

    Default

    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.
    OXpedia.org - the answer to almost all questions.

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