How to force Outlook Send SMTP Mail Certain Account

I have a customer who has an email account on his Exchange server and an external POP account.  He would like to use the Exchange server for internal communication only and force all SMTP mail to go out of the POP account.  I have set the POP account as a primary in Outlook and showed him how to use the accounts tab to send email out of the Exchange server account when he needs to but he would like to have Outlook automatically send all SMTP mail out of the POP account.  Do you have any suggestions?
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David LeeCommented:
Greetings, wducote.

There is no way I know of (I'm leaving room for an undocumented solution) to tell Outlook to send all external mail to POP and the internal to Exchange.  

In Outlook by default, it is set to send (or send replies) an email through the same account as it was originally recieved from.

Not to mention th implications that are involved when a corpoarte email is answered through a pop account of which your client may already know about.

As far as I know also, there is no other way except how you had guided the client to do this, by manually selecting the account.

However thinking a bit constructively - this is at BlueDevilFan :
If say we use Outlook 2003, and create a rule after highlighting Outbox,

Apply This Rule After The Message Arrives
through the <users exchange account>
and on this machine only
Run a <SCRIPT>  - ****
Except if from <domain exchange users>

Could a script be created to change the originating account (FROM) from exchange to pop? It will not run if the recipient address is within the same Exchange domain.

Is the above possible?
David LeeCommented:
Hi, upul007.

You've got an interesting idea there, but I don't think it will work with this question.  If I understand correctly, wducote's is talking about sending new messages, not replying to a message.  Rules only work with messages arriving in the Inbox or after sending.  After sending would be the closest to matching the condition for this question, but these rules fire after the message is gone, not as it's sending.  I thought about scripting and trapping the Send event which would give us a chance to inspect the message before it goes to the Inbox.  The problem though is what to do then.  If the message is addressed to a single recipient, then we'd have to determine if that recipient is in wducote's Exchange organization.  If they are, then we'd send through the Exchange account.  Otherwise, we'd send through the POP account.  There are a number of issues that'd have to be dealt with.  How do we determine who's in the Exchange organization?  The surest way would probably be to query Active Directory.  Or perhaps we could just look at the SMTP address and see if the domain matches the sender's domain.  Inspecting the address will trigger Outlook's built in security, so to avoid that we'd need a third-party tool.  Then there's the issue of sending from from a computer that didn't have this script on it, or sending from OWA.  This solution wouldn't work for either.  Finally, I'm not sure we can adjust the account a message is sent through in the Send event.  Frankly I've never tried doing that and don't know that Outlook exposes the necessary properties to make that possible.  There just is no good answer.  It would be nice if Microsoft would add this as a feature in a future version of Outlook.
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I have never set up a rule for the "Outbox", need to try that out.

Thanks BlueDevilFan for the explanation.


David LeeCommented:

> Ayubowan!
long life!

it is used as a greeting or farewell in my country to wish another a very long life.
David LeeCommented:
Thanks for the explanation.
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