Error sending email to random people

I have a user getting these kickbacks when they try to send email to certain outside addresses. They can send all other mail fine internally and externally. If anyone else tries to send to this addresses the email goes through just fine. The users can also send to this address successfully through OWA. This is starting to happen with multiple people and im not sure whats going on. This is happening with both outlook 2003 and 2007 on both XP or vista. Any help would be appreciated.

Your message did not reach some or all of the intended recipients.

      Subject:      test
      Sent:      11/7/2008 10:34 AM

The following recipient(s) could not be reached:

      "test@testdomain.com' on 11/7/2008 10:34 AM
            None of your e-mail accounts could send to this recipient.
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that1guy15Asked:
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GWMerrellCommented:
Check to see if your email server has been blacklisted:

http://www.mxtoolbox.com/blacklists.aspx
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97WideGlideCommented:
Sounds like a problem with your ISP - either you not authenticating correctly or the ISP refusing certain types of mail.  I would try the following two things to understand what is going on :

1)  Use your ISP's webmail interface to try to send the same mail and see what happens.

2) (Better) Enable logging in Outlook and scrutinize the smtp.log file.  Here's how to do it in Outlook 2007 :
TOOLS->OPTIONS->OTHER->ADVANCED OPTIONS->Enable Email Logging
Quit and restart

The log file should have some interesting information. You'll find it at:
C:\Documents and Settings\<logon name>\Local Settings\temp\OPMLOG.LOG

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that1guy15Author Commented:
I think if my exchange server was blacklisted the kickbacks would also come back for everyone. Also the same user can send to the same person with OWA just fine. That is my temporary work around right now until i can figure this out :)


97WideGlide: ill try the logging to see if anything will come up.

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GWMerrellCommented:
You post indicated that "certain outside addresses" were affected. Blacklisting doesn't happen all at once, hence only some mail domains may refuse where others will allow.

Testing:

1. Send email from OWA to one single address known to bounce from outlook.
2. Send email from Outlook to the same single address, does it fail?
3. If it fails, check your logs on your mail gateway device for that email, date and time. What information is provided?
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that1guy15Author Commented:
Testing:

1. Send email from OWA to one single address known to bounce from outlook.
--When sending from OWA the email goes just fine.

2. Send email from Outlook to the same single address, does it fail?
--When sending from Outlook the email kicks back

3. If it fails, check your logs on your mail gateway device for that email, date and time. What information is provided?
--mail server has nothing. It looks as if exchange never even saw an attempt to send the email.


You post indicated that "certain outside addresses" were affected. Blacklisting doesn't happen all at once, hence only some mail domains may refuse where others will allow.
--But this would still not explain why everyone can send to user@domain.net and one person can not. I would think that everyone would have the same issue if we were blacklisted.



Also outlook logs show nothing. This issue is actually starting to happen more and more. I have about 1 user a week complaining about it. Very strang??????


Thanks guys for all the help
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GWMerrellCommented:
Indeed this is strange.
Try this:

1. Put Outlook in Online mode

2. Emails sent, do they leave the outbox? ( If so, LOGCALB*  should have data on this mail transport )

3. Afte the client sends, is the message then in the send items? ( If so, there shoudl be transaction of the email, use message tracking to find the status, did go into exchange, leave exchange...etc )

This is a good place to stop, do let me know your results. :)
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GWMerrellCommented:
*** Disregard the LOGCALB*, this is only good for tracing calendar events.  Sorry.
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that1guy15Author Commented:
So the last email that i am working with went to 3 people. 1 person inside my domain, and 2 outside (2 different domains). The message made it to 2 of the 3.

Exchange shows the message going out to the person inside my domain and one of the others but does not show anything about the third email address.

Also in Message history the last line says
Message transferred to *******************************************************************************************
Not sure if this is anything.

Outlook sent items shows all three of them in the To: field
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that1guy15Author Commented:
Concerning that last line I found this post. i wonder if this could be it.
http://forums.msexchange.org/m_1800463634/mpage_1/key_/tm.htm#1800463634

I wonder if its the same Sembee?
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GWMerrellCommented:
based on your most recent information, that is a viable option.
Go with it and let us know. :)
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that1guy15Author Commented:
Hey everyone just letting you know i have not forgot about this. Its just with thanksgiving coming up and buisness slowing down i have not had a chance to troubleshoot further.

I will keep you informed
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that1guy15Author Commented:
I still have not been able to reproduce this or troubleshoot further. Thanks everyone for the help.
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