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What would be preventing a user from sending attachments?

Posted on 2006-05-31
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Last Modified: 2010-03-06
We have exchange 2003 with server 2003. A user that always was ableto send attchments all of a sudden gets those emails bounced back with a 550 code. I tested it with two emails, one with an attchment and the other without and the one without was delivered, and the one with the attchment was bounced. Same recipient address. I have a hunch that it's something in group policy, but that's only a hunch.
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Question by:dwielgosz
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by:Lee W, MVP
ID: 16799993
How large are the attachments - most mail servers have limits on attachment size.
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by:dwielgosz
ID: 16800144
small. our server is set to 20 meg. A couple of days ago I added to the server policy another email domain, actually two for incoming and outgoing mail on those domains in addition to our original email domain. I wonder if that somehow screwed things up? On the exchange server the application event viewer did have a comment about the failed email referring to address spaces on the connector and /or that it may be a dns lookup problem.
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by:Bembi
ID: 16800448
Maybe it helps, if you enable the SMTP log within your vortual SMTP server, there are sometimes more detailed failure information and the true error codes.

Also have a look at the size restictions, where you can setup limits to deny sending or receiving mails. Maybe the mailbox is near the limit. As all mails are also stored within the sent items folder, a mail with attachement will not be sent out due to this limitations, but a normal mail will still pass through.

Additional domains should not be the issue, as long as you have set them up within the recipient update policy.
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Author Comment

by:dwielgosz
ID: 16800643
yup, that's where I set those up
I'll look at the logs (are enabled)
where would I find the size restrictions for mailboxes?
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by:dwielgosz
ID: 16800660
I tested it with my account and my attachment was delivered so it is effecting only one user.
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Bembi earned 1500 total points
ID: 16800771
You can see, if your mail touches the log. If the mail (outgoing) touches the log files, it is gone through the server and there is an issue with the receiving server.

If this is only inside (from internal user to internal user), the SMTP log is not touched anyway as long as you do not have them on two different servers. In that case, you should enable / have a look at the tracking log. There you may find additional information. In that case (or also for outbound mail, which do not reach the Virtual SMTP Server  / log)), you can freeze all queues in EMC and the release on queue after each other. Doing so, you can determine, where the mail is rejected and this may point you to the real issue.

Have you tried to send the attachement to different users?
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Author Comment

by:dwielgosz
ID: 16800839
it's not the same attachment. it's different attachments to different receivers, all external. only from this one sender that has admin rights on hiis pc

where is the smtp log? is that program files/exchsrvr/server.logs/*.log ?
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by:Bembi
ID: 16800887
No, this is the tracking log.

To see the SMTP log, you have to enable logging within your Virtual SMTP server. The log itself is written into the
C:\Windows\System32\logfiles folder into a subdirectory (by default, can be also set).
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Expert Comment

by:mkumar23
ID: 16800958
Can you also put the message body of bounced back email with error 550?
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Author Comment

by:dwielgosz
ID: 16801056
problem solved. somehow, the user's account settings changed. A long time ago he had problems with his logon profile and we set up a temporary account for him. The account was long ago deleted but when I examined his exchange properties, specifically the smtp addresses associated with his account, I saw that the temporary email address was specified as his primary account. I specified the correct account and deleted the old and applied. Had him retest and is now able to send attachments. I've got a hunch that somehow old setting for him were replicated back from the netherworld???
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Author Comment

by:dwielgosz
ID: 16807208
Although this answer didn't exactly solve the problem that was occurring, the information is extremely usefull to know for tracing messages. Thanks for the help.
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