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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?

ICG

ASKER

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.

Amit

Enable message tracking and the test it. See where it is failing. Secondly, it is with same user? Remove Cache mode and try again.

ICG

ASKER

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.

Amit

Ya Messaging tracking will show, where it is failing...If possible change user machine and test it.

ICG

ASKER

The message details show the message was sent/delivered successfully but does not mention the attachment.

marpanet

This only happends when sending from Outlook 2011?, did you try the same user sending from Pc Oulook 2010?

Amit

http://www.officeformac.com/ms/ProductForums/Outlook/3412

ICG

ASKER

@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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ICG

ASKER

Called Microsoft for solution.