One of my employees is having trouble sending mail with attachments to an external party. We're using Outlook 2010 in conjunction with Exchange 2010 Standard.

Here's what I've deduced so far:

  1. Sending from employee's mailbox on employee's PC to external party - email arrives with no attachment
  2. Sending from employee's mailbox via OWA to external party - email arrives with attachment
  3. Sending from my mailbox on employee's PC to external party - email arrives with attachment
  4. Sending from employee's mailbox on my PC to external party - email arrives without attachment
  5. Sending from employee's mailbox on my PC to my gmail account - email arrives with attachment

In all cases where the email does not arrive with the attachment, pulling the message up in OWA does show the attachment intact.

Initially I thought it was an issue with his Outlook setup, but now I'm not sure. The attachment is innocuous and actually doesn't appear to matter... We're trying to send a PDF but other types like images don't arrive either in the same circumstances as above.

At this point I have no idea what the issue could be. The recipient mailbox is hosted by a local ISP, so I have an idea he should maybe be reaching out to them, but the circumstances above are so bizarre I don't think they would be able to help. Can anyone suggest what might be going on here?

EDIT: I've just found out that this is affecting at least one other employee as well.

I know that your Exchange mailbox retains some information about Outlook properties... If I customize my view in Outlook, say, and move to another PC and load up my mailbox it brings those settings along. Is it possible to clear or reset these settings in an Exchange mailbox?

  • Sounds like you've spent more than enough time on this to justify re-imaging the employee's PC and moving onto more important problems. If you don't have more important problems and are incredibly bored, I always have paperwork that needs doing, and I'd be happy to let you do it for me. – HopelessN00b Jan 30 '14 at 22:09
  • Why do you imagine this has something to do with his PC? If I use my mailbox on his PC, it works. If I use his mailbox on my PC, it doesn't work. But it's not that his mailbox is shot because it works out of OWA just fine. Did you actually read anything I wrote above? – NaOH Jan 30 '14 at 22:18

OWA is basically/essentially a client-less connection to the user's mailbox in Exchange. For the purposes of troubleshooting user-email issues, you should consider what you see in OWA to be what is actually on the server.

Therefore, the fact that attachments send properly in OWA, but not from an Outlook client tells you that the problem, is, in fact, something with the client (Outlook) or client PC. The fact that sending attachments also fails for the same user, on a different PC, tells you that the problem isn't specific to the PC, but follows the user.

What follows the user from PC to PC? The user profile, primarily. You haven't said if you have roaming profiles or included enough detail to explore and pinpoint the cause of the issue, but we do know that the issue is a client-based issue, so focus there. First thing I'd check is user-created rules in Outlook, because that's often a minefield, and following that, flush the client-side cache, check your GPOs, try rebuilding the user profile (maybe even create a new user profile, for this user), and depending on the user profile settings in your environment, even reinstalling Outlook, or re-imaging the PC may be appropriate.

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  • I might suggest exporting the rules and then starting Outlook as such from the Run dialog: outlook.exe /cleanrules. This will clean both client and server side rules. If the problem is resolved after that you can import the exported rules, verify whether or not the problem returns and then diagnose the rules one at a time. – joeqwerty Jan 30 '14 at 23:13
  • Sorry, should have been clearer. I added a profile for him on my PC signed into Windows as myself, not as him. We do not have roaming profiles enabled. Also, just checked, user has no rules in Outlook (beyond the default "clear all flags" or whatever). – NaOH Jan 30 '14 at 23:32

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