Exchange Server 2003 SMTP

[jschwartz73]

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.

[jjzhuang]

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!

[jschwartz73]

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

[jjzhuang]

Can you telnet to that port?

[jschwartz73]

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

[jjzhuang]

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

[jschwartz73]

Bug filed, number 26452

Bug 26452 - Cannot send E-mail with Exchange Server 2003 SMTP

Thanks for your help.

[jschwartz73]

I just updated the bug with some additional information, but I thought I'd share how to turn on STARTTLS through Zimbra Desktop:

Add the following to your localconfig.xml

<key name="javamail_smtp_enable_starttls">
<value>true</value>
</key>

However, I now get a different problem when trying to send email from this exchange account:

2008-04-05 23:15:33,085 WARN [sync-timer-user@somemeailserver.com] [] smtp - exception occurred during SendMsg
com.zimbra.cs.mailbox.MailSender$SafeMessagingExce ption: Default SSL context init failed: null; chained exception is:
java.net.SocketException: Default SSL context init failed: null
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTrans port.java:1326)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SM TPTransport.java:407)
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)
2008-04-05 23:15:33,088 DEBUG [sync-timer-user@somemeailserver.com] [] offline - smtp: failed to send mail (385): ZMail helloworld
com.zimbra.common.service.ServiceException: system failure: MessagingException
ExceptionId:mylaptop:sync-timer-user@somemeailserver.com:1207455333087:978a898074c eac46
Code:service.FAILURE
at com.zimbra.common.service.ServiceException.FAILURE (ServiceException.java:217)
at com.zimbra.cs.mailbox.MailSender.sendMimeMessage(M ailSender.java:315)
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$1.run(Desktop Mailbox.java:85)
at java.util.TimerThread.mainLoop(Unknown Source)
at java.util.TimerThread.run(Unknown Source)
Caused by: com.zimbra.cs.mailbox.MailSender$SafeMessagingExce ption: Default SSL context init failed: null; chained exception is:
java.net.SocketException: Default SSL context init failed: null
at com.sun.mail.smtp.SMTPTransport.startTLS(SMTPTrans port.java:1326)
at com.sun.mail.smtp.SMTPTransport.protocolConnect(SM TPTransport.java:407)
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)
... 6 more
2008-04-05 23:15:33,088 INFO [sync-timer-user@somemeailserver.com] [] offline - SMTP send failure: ZMail helloworld

I've been through the source forward and back and can't seem to figure it out. I also have a small test program that works fine.

Any thoughts?

Does anybody have zimbra desktop working with Exchange Server 2003?

Thanks in advance.

[jjzhuang]

Could you please file a bug? Thanks!