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I have a user that occasionally does not receive emails from outside our organization. It does not seem to matter whether the other person is replying to an initial email or sending a new message.

I have checked the Exchange System Manager and there is no record of the sender at all during this time period. No record of the message getting captured by the spam software (GFI Mail Essentials). The sender does not receive an NDR or any other indication that the message didn't arrive.

It seems to me that these messages are not even getting to our servers at all. But, this is only impacting one user(that I am aware of) and not all the time. Some messages get through without any problem, others just disappear.

The senders are not related at all. One is in another country, one uses AOL, one uses a corporate Exchange server locally. I can't seem to find a pattern.

Where else can I look to try to figure out where these messages are going/getting captured? Are there additional logs that I can enable either within GFI or Exchange that might shed some light on this?

Thanks.

We are using Exchange 2003 on Server 2003. Desktop client is Outlook 2003 on Windows XP Pro.

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2 Answers 2

up vote 1 down vote accepted

You can enable SMTP logging in the Exchange System Manager and see if you ever see a connection in that.

Administrative Groups :: Your Group :: Servers :: The Server :: Protocols :: SMTP :: Right Click Default SMTP Server :: Enable Logging in the General Tab.

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I enabled logging. I'll report back. Thanks. –  minamhere Oct 29 '09 at 19:57
    
It turned out that we had a "retired" Exchange server still in the organization. It was collecting some of the messages and not delivering them properly. Enabling logging turned me on to this issue. Thanks. –  minamhere Jan 5 '11 at 5:00

Have you verified that the senders ip isn't blacklisted?

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I have not checked, but if it were, shouldn't it show up in my spam blacklist logs? I guess an intermediate mail server could be blocking against a blacklist? –  minamhere Oct 29 '09 at 19:54

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