Send secure SMTP from Outlook/Thunderbird/Scanner? (Full Version)

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mvalpreda -> Send secure SMTP from Outlook/Thunderbird/Scanner? (27.Aug.2013 8:50:24 PM)

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" ?

thedriver -> RE: Send secure SMTP from Outlook/Thunderbird/Scanner? (15.May2014 7:38:00 AM)

Did you resolve this?
I need scanners on external dynamic IPs to be able to send via email authentiating on our server.
I used to be able to do this with Ex2003. But can't seem to get this working with 2010.
If I specify an IP Address it works (but only as long as that IP is valid). As soon as their ISP changes issues a new IP it no longer works. If I specify a range of address for the receive connector (e.g. - it doesn't work.

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