Had a bit of a strange one on a recent Exchange 2010 migration from Exchange 2003.  Email sent from a Hotmail account with two PDFs but the attachments did not show in Outlook (2010 or 2013, 2003 untested).  When viewing the properties of the email it reported the correct size of the total of the attachments, but no paper clip icon.  If the user logged into OWA the paper clip attachment icon shows and the two attachments were present.

When the same email was sent to a user whose mailbox was still on 2003 the attachments were visible in Outlook. At this stage incoming email was still on the original Exchange 2003 server as it had not been moved to the new Exchange 2010 server.  So it is clear that the two Exchange servers were handling this problematic email differently.

A quick scour of the web found this very useful post, but it was difficult to find.  Here is a précis of the post:

Solution to Outlook Attachments Not Showing

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I recently did an Exchange 2003 to Exchange 2010 migration and one of the Mac users reported a problem when trying to send large (~20MB) emails.  Even though I had removed all transport settings, mailbox settings, organisation settings which might be interfering, after further digging I found the Mac version of Outlook connects via EWS (Exchange Web Services) and this has a separate email limit.  There are many other references of this on the web with various commands and files to edit which people claim solve the problem.  There appears some confusion over the value of the numbers to enter in the web.config – in some versions of Exchange they are in bytes, in others they are in kilobytes.  Here is my fix:


Error seen on user’s computer:

Could not synchronize record: xxxxx to Exchange server: server

With the Error Code: -18493

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