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Trouble sending attachments with Mac Outlook 2011 / Exchange 2010

We have Exchange 2010 on Server 2008 R2. One user is using Mac Outlook 2011. When he tries to send attachments to some of our clients, the attachments do not show up. If he sends attachments to a Yahoo, MSN or Gmail account, they show fine.

If he sends attachments to the clients with OWA or Outlook 2010 on Windows, the attachments go through fine.

His OWA Sent folder shows all emails having attachments.

The file size is less than 100kb and all of his email's are going out in HTML.

Are there any additional client-side or server-side configurations we need to do to resolve this issue with attachments for Mac Outlook 2011?
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ICG
Asked:
ICG
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1 Solution
 
ICGAuthor Commented:
Update: If he sends the attachment to just the outside email address now, they get it fine. If he sends the email to just an internal person, they get it fine. If he sends it to both in the same email, the outside person gets it but not the internal person.
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AmitIT ArchitectCommented:
Enable message tracking and the test it. See where it is failing. Secondly, it is with same user? Remove Cache mode and try again.
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ICGAuthor Commented:
Does the message tracking actually show when an attachment is dropped or just when the message itself fails to be delivered?

Also, we tried removing the Cache mode as well as deleting the users profile on the Mac and starting over on it. Both yielded the same issue.
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AmitIT ArchitectCommented:
Ya Messaging tracking will show, where it is failing...If possible change user machine and test it.
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ICGAuthor Commented:
The message details show the message was sent/delivered successfully but does not mention the attachment.
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marpanetCommented:
This only happends when sending from Outlook 2011?, did you try the same user sending from Pc Oulook 2010?
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ICGAuthor Commented:
@amitkulshrestha: That post was posted by the user having difficulty.  The issue is not related to that solution.  In face, that solution prevented user from even accessing Outlook.
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ICGAuthor Commented:
After many calls with Microsoft, we discovered it is a bug into Mac Office 2011. It has to do with how the Mac OS itself handles attachments; it automatically makes them all inline.

The only workaround they were able to advise at this time was for the user to send all emails as Plain Text instead of RTF. After trying this solution, all recipients were able to receive the attachments correctly as long as the email was plain text.
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ICGAuthor Commented:
Called Microsoft for solution.
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