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Send secure SMTP from Outlook/Thunderbird/Scanner?

    Question

  • I have a requirement to be able to send secure email from outside our network. This could be from Outlook, Thunderbird or a scanner with email capabilities.

    I set up a new receive connector in Exchange 2010 EMC:
    Name: Secure Outside Relay
    HELO response: FQDN of our SSL certificate (same as OWA, Outlook Anywhere, etc)
    Port: 587
    IPs: Any
    Authentication: TLS (not mutual or anything else)
    Permission group: Exchange users, Exchange servers

    That is all I have set up.

    When I try and send from Outlook I keep getting a password prompt. Outlook says "0x800CCC92 Your e-mail server rejected your login." I have tried just username, email address and domain\username. No dice.

    Outlook is set up with port 587 and to use TLS.

    I see an "Audit Success" on the Exchange server with my attempt.

    Do I need to add
    Get-ReceiveConnector "Secure Outside Relay" | Add-ADPermission -User "NT AUTHORITY\ANONYMOUS LOGON" -ExtendedRights "Ms-Exch-SMTP-Accept-Any-Recipient" ?
    Wednesday, August 28, 2013 2:00 AM

Answers

  • For Outlook, you shouldn't have to do anything.  Use Outlook Anywhere.  Of course, you can use Outlook with an IMAP profile to test as you have been doing.

    Why did you create a separate connector rather than just modifying the Client connector that's already bound to port 587?  Having two connectors bound to the same IP addresses and port is likely to cause confusion unless you have some other way of distinguishing which is to be used by the clients.


    Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

    Wednesday, August 28, 2013 3:30 AM