The inline image of an email message that is sent by using OWA with S/MIME enabled is lost for an Exchange Server 2007 user

Symptoms

Consider the following scenario:
  • You apply Update Rollup 2 for Microsoft Exchange Server 2007 Service Pack 2 (SP2) on an Exchange Server 2007 server.
  • A user accesses a mailbox that is hosted on the Exchange Server 2007 server by using Outlook Web Access (OWA) with S/MIME enabled.
  • The user creates an email message and then paste an image in this email message.
In this scenario, the image displays as expected in the OWA composing window. However, the image is lost if you view the email message from Sent Items. Additionally, the image is also lost if a recipient views the email message. If the recipient tries to forward this message, a red X image with the title Untitled1.png is displayed.  

Resolution

To resolve this problem, install the following update rollup:
2279665 Description of Update Rollup 1 for Exchange Server 2007 Service Pack 3

Status

Microsoft has confirmed that this is a problem in the Microsoft products that are listed in the "Applies to" section.