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Outlook doesn't resolve 'From' field

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  • Outlook doesn't resolve 'From' field


    I have an Exchange server with several users having two mailboxes to handle emails from separate domains. It works OK as long as the user populates the 'From' field by clicking the 'From' button, then selecting the appropriate account to send from. However, if he manually types in the email address, Outlook does not resolve it to the AD account name (should show the name underlined), and the result will be that the mail, if sent, comes back with a "You do not have permission to send to this recipient error".

    One caveat with my setup is this -

    Account one is, say, [email protected]
    Account two is [email protected]

    In AD, the logon name for account 1 is [email protected]. The logon name for account 2 can only be for domain, so I made it [email protected] to differentiate it. In AD, on the 'Email Addresses' tab, I have [email protected] as the default SMTP address, and [email protected] as a secondary SMTP address. This is necessary for my SMTP email program to connect with the mailbox.

    In any event, manually putting '[email protected]' or '[email protected]' into Outlook's 'From' field does not result in Outlook resolving the email address to Tom's account, and sending the email as such results in an error. If Tom manually selects either account from the GAL, everything works fine. Permissions are such that [email protected] and [email protected] have full mailbox access to each other's account.