In Windows XP SP2 and above (not sure if this applies to Vista), Microsoft implemented stricter security policies on sending credentials and cookies via Outlook when it is accessing an email that contains linked content / images.
This causes each object / image in the email to require manual authentication. Each object will prompted for, making it cumbersome to read emails with many linked objects.
There is a hot fix provided to 'fix' this issue. The KB article linked to the hotfix is 895948. This article is PRIVATE and thus cannot be found by searching the Microsoft website.
In order to get this hotfix, you will need to contact Microsoft at 1-800-936-4900. You can reference IronPort case number SRX070910600725
IronPort does not have any knowledge in automatically deploying this hotfix to the clients on the network. It is possible that a NETLOGON batch file could be used to implement this. The hotfix contains several files that need to overwrite local Outlook files as well as a registry key to change.
Microsoft's official workaround is to only use email where the images are embedded into the email, not linked.
IP credential cache can be used instead of Cookie. This would allow the WSA to only need to authenticate the client once from their IP within the credential cache timeout. Please note that unless they authenticate with IE first, they will still be prompted for auth the first time they access an object via Outlook.
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