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For some reason I am having an unusually hard time finding the answer to this question: If I open Outlook in one AD site and my mailbox is in another (on a separate database), how is the mailbox accessed? Is it through the hub transport role? I am trying to find documentation that outlines how this information flows.

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It should be the CAS server role. This is the role that authenticates clients and routes you to your proper mailbox server (if it isn't the same server). There should be at least one CAS server role in each AD site that holds a mailbox server.

The hub transport role is responsible for mail flow (delivering mail between your mailbox and another for instance), transport rules between mailbox servers.

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