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In an Exchange Server 2007 Service Pack 1 (SP1) environment, when you use Outlook Web Access (OWA) with S/MIME installed to send a message that includes a large attachment, an HTTP 500 error resembling the following is returned:
This issue occurs when the network bandwidth between OWA and Exchange Server 2007 SP1 is limited. When an OWA client does not have S/MIME installed, many time-out values are reset. However, when S/MIME is installed on the OWA client, the time-out error occurs.
To resolve this problem, install Update Rollup 9 for Exchange 2007 Service Pack 1. For more information about Update Rollup 9 for Exchange Server 2007 Service Pack 1, see the following Exchange Help topic: