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Are you using a client-side rule or a server-side rule? If you examine the rule in Outlook, it should identify its type. If the type is client-side, then Outlook will need to be running when the message arrives, or the rule will not be processed. If you are using a server-side rule, check the properties of the IMC and make sure it is configured to allow this. If it is, then use Network Monitor to trace the network traffic while sending test messages that should trigger the rule. This will at least tell you if the Outlook client is sending the e-mail or not.
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