Iphone and Exchange 2010 error “Cannot Send Mail: an Error occurred while delivering this message”

Problem:  Trying to forward some pictures I took on my iPhone via email. The total size for the attachments was about 20MB.   After sending I got the following error message:

“Cannot Send Mail:  An error occurred while delivering this message”


“Cannot Send Mail:  The message was rejected by the server”

Solution:  I checked the exchange logs and got an Event ID 1008.  The event talked about an outdated or corrupt partnership with my iPhone.  I also noticed another messages stating the “Maximum request length exceeded”  Which brought me to the solution.   I followed the directions in the following Technet blog article(link below).  Changed the <httpRuntime maxRequestLength=”10240″/>  setting to “25600” or 25MB on my CAS server.   Once the change was made, the emails passed without error.


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