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Hope someone can help with this one.

Scenario is an internal Exchange 2003 server. OWA front end server in the DMZ. OWA logins work fine, with SSL configured.

Over the last week (3 times so far) when an internal person opens their Outlook and then tries to open an email with JPG attachments they are prompted for the webmail login. Why? Even if they enter their valid webmail OWA login it fails and reprompts once for each attachment. Once they get through the multiple login prompts, they can double-click to open the attachments, but they are all blank.

Any ideas on what could cause this? Why would someone accessing an email from an internal Outlook client get prompted for details of the OWA/webmail server login?

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Looks like I found the answer. The OWA server still had the EX Info Store service running. I think that because of this if someone from within the company sent and email to someone else within the company, then it was held on the OWA server. So when the internal person checked their email they got prompted for the webmail server login as the OWA was storing the email rather than auto-forwarding to the internal exchange server.

A unique combo, but maybe this will help someone else. I didn't find any other reference to this when hunting around google.

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