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Microsoft Exchange Server 2003 can't send to yahoo addresses

Posted on 2008-10-02
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I have a client that has asked me to figure out why he can't send email to any yahoo addresses.  He's running his own Exchange server on SBS 2003.  The problem affects all network users and all workstations, so it's not a workstation or profile setting.  First thing I did was turned on logging for the Exchange SMTP transport protocol.  I turned on every logging option I could find, to get the most verbose information possible.  The funny part about this is, it logged various emails being sent, but absolutely no emails being sent (or rejected) to a yahoo address (and he sent about 3 test emails while the logging was enabled).  Absolutely nothing turned up in the Event Viewer either.  So I turned on Transport Logging from within Outlook and came up with the attached log.

This of course shows that everything worked exactly as it should of, but it did not.  I never received the test email that was sent.  The emails aren't being bounced back.  I don't know what else to look at.
2008.10.02 16:28:35 <<<< Logging Started (level is LTF_TRACE) >>>>
2008.10.02 16:28:35 Microsoft Exchange Server: Synch operation started (flags = 00000001)
2008.10.02 16:28:35 Microsoft Exchange Server: UploadItems: 1 messages to send
2008.10.02 16:28:35 EXECUTING Put MAPI TASK
2008.10.02 16:28:36 Starting the Spooling Cycle
2008.10.02 16:28:36 MAPI Status: (IN -- ---/OUT fl ---)
2008.10.02 16:28:36 MAPI XP Call: FlushQueues, hr = 0x00000000, ulFlushFlags = 0x0000001a
2008.10.02 16:28:36 Sending one message
2008.10.02 16:28:36 Progress: Sending message 'testing' (size 2.21 KBytes)
2008.10.02 16:28:36 MAPI Status: (IN -- ---/OUT fl act)
2008.10.02 16:28:36 MAPI Status: (IN -- ---/OUT fl ---)
2008.10.02 16:28:36 MAPI XP Call: SubmitMessage, hr = 0x00000000
2008.10.02 16:28:36 MAPI XP Call: EndMessage, hr = 0x00000000
2008.10.02 16:28:36 FINISHED MAPI TASK
2008.10.02 16:28:36 Microsoft Exchange Server: ReportStatus: RSF_COMPLETED, hr = 0x00000000
2008.10.02 16:28:36 Microsoft Exchange Server: Synch operation completed

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Question by:LinuxNtwrkng
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by:ecsrd
ID: 22630018
Have you checked if his mail server is blacklisted?  Does it have an SPF record?  Do any other domains not receive email?
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by:debuggerau
ID: 22630057
does it appear in the exchange queue when you look in system manager?
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by:lakshmidurga
ID: 22630253
go to www.mxtoolbox.com to check whether your site is blacklisted. if yes try to remove it from blacklist.
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by:ARKLightning
ARKLightning earned 100 total points
ID: 22632267
As debuggerau pointed out,  if your not seeing it in the SMTP log's it indicates it's queuing .  Launch Exchange System Manager, Expand servers, #YOURSERVER#, Queues and you should see in the right hand pane something like  yahoo.co.uk  connection state scheduled.  Right click on it and force connection.
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by:LinuxNtwrkng
ID: 22639115
Mail server is not blacklisted, yahoo.com does show up in the queues list.  If I right-click it and select "force connection" it shows as "active" in Exchange System Manager.  So I went back to a workstation and tried sending another email, but had the same issue.  No errors, no bounced email, but also no read receipt was received and I never got the email at my yahoo address either.
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by:LinuxNtwrkng
ID: 22639119
Excuse me.. No delievery receipt was received.  Not read receipt.
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by:lakshmidurga
ID: 22654838
can you check whether it is getting blocked in your spam filter -if you enable the option to check for outgoing mail
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by:LinuxNtwrkng
ID: 22660950
lakshmidurga,

Not sure I understand what you're saying.  Does Exchange have a built in spam filter?  As far as external filters I'll double check, but I don't believe he has one.
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debuggerau earned 400 total points
ID: 22674386
An outbound spam filter, now that's an idea that MS could use....

In the Queues, it should specify why it is delayed and we can work from there...

Also, If your concerned about the connection, have you tried a basic telnet test for SMTP with Yahoo from your connection?
http://exchange.mvps.org/smtp_frames.htm

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by:lakshmidurga
ID: 22684658
i was talking about thrid party filters like GFI mime sweeper....most of the times it gets blocked in spam filtering..even we had the same problem with yahoo(yahoo.com and yahoo.co.in) when user sending messages from yahoo.com they were able to send and when they try sending from yahoo.co.in they were not able to send...it was becos of the advertisements in each. there was a word that was matching with spam filter words. so you need to check it carefuly...
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by:LinuxNtwrkng
ID: 22715899
He has no 3rd party spam filtering.  Here's another interesting tidbit I found yesterday.  He came over and said "What did you do to fix the server?"  I told him that I'd not done anything except click "force connection" which only worked the one time.  He informed me that his yahoo clients are receiving his emails now.  So, as a test, I logged into his network and sent a test email to my yahoo account.  The message went into the Exchange queue, the queue was listed as "Active", yet my message stayed there and was never received at my yahoo address.

Am I the only one getting more and more confused here?  :)  Can you tell I'm not an Exchange admin?  heh.
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by:debuggerau
ID: 22716933
I'd be careful when thinking any mail server is functioning well 'all' the time...

Try the tests I suggested above and you will get some in-site.
But I would also enable the SMTP detailed logs (maximum) and see the handshaking taking place, if its getting into the yahoo server, it may be tripping their filters...
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by:LinuxNtwrkng
ID: 31597319
The help provided was great.  Thank you for your insights.  Unfortunately I'm not exactly sure what was causing the issue, as I mentioned before, I'd enabled maximum logging before and the logs showed absolutely no errors, yet the recipient wasn't getting the emails.  Then one day, she started getting them.  I didn't change anything from the one day to the next. so... *shrug*  Thank you though!
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