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Thread: Exchange Server 2003 SMTP

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  1. #1
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    Default Exchange Server 2003 SMTP

    I setup zimbra desktop as a front-end to my company's MS Exchange server. Since I use firefox, the MS Exchange OWA is severly crippled.

    In any event, I'm having trouble getting ZD to send email via the company exchange server. I can receive email just fine. I know the settings are correct. The log file shows this error:

    2008-03-25 21:13:43,163 WARN [sync-timer-jschwartz73@someemailserver.com] [] smtp - exception occurred during SendMsg
    com.zimbra.cs.mailbox.MailSender$SafeMessagingExce ption: Unrecognized SSL message, plaintext connection?; chained exception is:
    javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?
    at com.sun.mail.smtp.SMTPTransport.readServerResponse (SMTPTransport.java:1598)
    at com.sun.mail.smtp.SMTPTransport.openServer(SMTPTra nsport.java:1356)
    at com.sun.mail.smtp.SMTPTransport.protocolConnect(SM TPTransport.java:399)
    at javax.mail.Service.connect(Service.java:297)
    at javax.mail.Service.connect(Service.java:156)
    at javax.mail.Service.connect(Service.java:105)
    at javax.mail.Transport.send0(Transport.java:168)
    at javax.mail.Transport.send(Transport.java:98)
    at com.zimbra.cs.mailbox.MailSender.sendMessage(MailS ender.java:428)
    at com.zimbra.cs.mailbox.MailSender.sendMimeMessage(M ailSender.java:248)
    at com.zimbra.cs.mailbox.LocalMailbox.sendPendingMess ages(LocalMailbox.java:155)
    at com.zimbra.cs.mailbox.LocalMailbox.sync(LocalMailb ox.java:293)
    at com.zimbra.cs.mailbox.LocalMailbox.syncOnTimer(Loc alMailbox.java:236)
    at com.zimbra.cs.mailbox.DesktopMailbox$1.run(Desktop Mailbox.java:85)
    at java.util.TimerThread.mainLoop(Unknown Source)
    at java.util.TimerThread.run(Unknown Source)

    I've tried different variations of my username as well as shutting off the SSL as the error message suggests. Nothing seems to work. The only thing interesting about our company email setup is the SSL for SMTP is on port 465.

    Any suggestions?

    On a side note, ZD is working great with my yahoo plus, gmail and another pop3 account i have.

  2. #2
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    You can turn on SMTP tracing to help debugging the problem. Edit <install>/conf/localconfig.xml and add a key of "javamail_smtp_debug" with value of "true". Then restart the background service (see wiki if you don't know how) and the SMTP trace will go into <install>/log/zdesktop.out. Thanks!

  3. #3
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    Thanks for your quick response.

    I enabled the SMTP logging as directed. The results are below, the
    last few lines just keep repeating.

    Any help would be greatly appreciated. This will make an excellent email client once fully configured!

    0 INFO [main] log - Logging to org.slf4j.impl.Log4jLoggerAdapter(org.mortbay.log) via org.mortbay.log.Slf4jLog
    1482 INFO [main] log - jetty-6.1.5
    1887 INFO [main] log - No Transaction manager found - if your webapp requires one, please configure one.
    DEBUG: setDebug: JavaMail version 1.4.1ea-SNAPSHOT
    DEBUG: setDebug: JavaMail version 1.4.1ea-SNAPSHOT
    DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport ,Sun Microsystems, Inc]
    DEBUG SMTP: useEhlo true, useAuth true
    DEBUG SMTP: useEhlo true, useAuth true
    DEBUG SMTP: trying to connect to host "email.someemailserver.com", port 465, isSSL true
    DEBUG: setDebug: JavaMail version 1.4.1ea-SNAPSHOT
    DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport ,Sun Microsystems, Inc]
    DEBUG SMTP: useEhlo true, useAuth true
    DEBUG SMTP: useEhlo true, useAuth true
    DEBUG SMTP: trying to connect to host "email.someemailserver.com", port 465, isSSL true

  4. #4
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    Can you telnet to that port?

  5. #5
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    My apologies, in an effort to troubleshoot, I tried some other potential ports. The actual port is: 587

    When I saw the
    DEBUG SMTP: exception reading response: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

    I changed the connection and unchecked the SSL checkbox.

    Here is the information from the log:

    DEBUG SMTP: trying to connect to host "email.someemailserver.com", port 587, isSSL true

    DEBUG SMTP: exception reading response: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

    DEBUG: setDebug: JavaMail version 1.4.1ea-SNAPSHOT

    DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SMTPSSLTransport ,Sun Microsystems, Inc]

    DEBUG SMTP: useEhlo true, useAuth true

    DEBUG SMTP: useEhlo true, useAuth true

    DEBUG SMTP: trying to connect to host "email.someemailserver.com", port 587, isSSL true

    DEBUG SMTP: exception reading response: javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?

    DEBUG: setDebug: JavaMail version 1.4.1ea-SNAPSHOT

    DEBUG: getProvider() returning javax.mail.Provider[TRANSPORT,smtp,com.sun.mail.smtp.SMTPTransport,Sun Microsystems, Inc]

    DEBUG SMTP: useEhlo true, useAuth true

    DEBUG SMTP: useEhlo true, useAuth true

    DEBUG SMTP: trying to connect to host "email.someemailserver.com", port 587, isSSL false

    220 ford.someemailserver.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at Thu, 27 Mar 2008 10:16:15 -0500

    DEBUG SMTP: connected to host "email.someemailserver.com", port: 587


    EHLO dim4700-vista.gateway.2wire.net

    250-ford.someemailserver.local Hello [ww.xx.yy.zz]

    250-TURN

    250-SIZE

    250-ETRN

    250-PIPELINING

    250-DSN

    250-ENHANCEDSTATUSCODES

    250-8bitmime

    250-BINARYMIME

    250-CHUNKING

    250-VRFY

    250-TLS

    250-STARTTLS

    250-X-EXPS GSSAPI NTLM

    250-AUTH GSSAPI NTLM

    250-X-LINK2STATE

    250-XEXCH50

    250 OK

    DEBUG SMTP: Found extension "TURN", arg ""

    DEBUG SMTP: Found extension "SIZE", arg ""

    DEBUG SMTP: Found extension "ETRN", arg ""

    DEBUG SMTP: Found extension "PIPELINING", arg ""

    DEBUG SMTP: Found extension "DSN", arg ""

    DEBUG SMTP: Found extension "ENHANCEDSTATUSCODES", arg ""

    DEBUG SMTP: Found extension "8bitmime", arg ""

    DEBUG SMTP: Found extension "BINARYMIME", arg ""

    DEBUG SMTP: Found extension "CHUNKING", arg ""

    DEBUG SMTP: Found extension "VRFY", arg ""

    DEBUG SMTP: Found extension "TLS", arg ""

    DEBUG SMTP: Found extension "STARTTLS", arg ""

    DEBUG SMTP: Found extension "X-EXPS", arg "GSSAPI NTLM"

    DEBUG SMTP: Found extension "AUTH", arg "GSSAPI NTLM"

    DEBUG SMTP: Found extension "X-LINK2STATE", arg ""

    DEBUG SMTP: Found extension "XEXCH50", arg ""

    DEBUG SMTP: Found extension "OK", arg ""

    DEBUG SMTP: Attempt to authenticate

    DEBUG SMTP: use8bit false

    MAIL FROM:<jschwartz@someemailserver.com>

    530 5.7.0 Must issue a STARTTLS command first

    DEBUG SMTP: got response code 530, with response: 530 5.7.0 Must issue a STARTTLS command first


    RSET

    530 5.7.0 Must issue a STARTTLS command first

    javax.mail.MessagingException: 530 5.7.0 Must issue a STARTTLS command first


    at com.sun.mail.smtp.SMTPTransport.issueCommand(SMTPT ransport.java:1468)

    at com.sun.mail.smtp.SMTPTransport.issueSendCommand(S MTPTransport.java:1499)

    at com.sun.mail.smtp.SMTPTransport.mailFrom(SMTPTrans port.java:1041)

    at com.sun.mail.smtp.SMTPTransport.sendMessage(SMTPTr ansport.java:621)

    at javax.mail.Transport.send0(Transport.java:169)

    at javax.mail.Transport.send(Transport.java:98)

    at com.zimbra.cs.mailbox.MailSender.sendMessage(MailS ender.java:428)

    at com.zimbra.cs.mailbox.MailSender.sendMimeMessage(M ailSender.java:248)

    at com.zimbra.cs.mailbox.LocalMailbox.sendPendingMess ages(LocalMailbox.java:155)

    at com.zimbra.cs.mailbox.LocalMailbox.sync(LocalMailb ox.java:293)

    at com.zimbra.cs.mailbox.LocalMailbox.syncOnTimer(Loc alMailbox.java:236)

    at com.zimbra.cs.mailbox.DesktopMailbox$1.run(Desktop Mailbox.java:85)

    at java.util.TimerThread.mainLoop(Unknown Source)

    at java.util.TimerThread.run(Unknown Source)

    QUIT

    221 2.0.0 ford.someemailserver.local Service closing transmission channel

  6. #6
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    OK got it. Please file a bug with your latest SMTP trace. Thanks!

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