550 5.7.1 Unable to relay for user@domain.com

Trying to setup exchange 2003 to allow users to relay mail through the exchange server. We have 2 exchange servers at 2 different locations for 2 different companies. What I'm trying to accomplish is have company A attached to outlook as a exchange account then have company B attached to outlook as a pop 3 account.

Currently I'm only trying to accomplish this for only one user, the vice president who needs to send and receive emails from both companies through his outlook profile. He has an account on both domains and can authenticate via outlook no problems.  The issue that I'm having is when he tries to send an email from the pop account we get a message back from the system administrator:

Your message did not reach some or all of the intended recipients.
      Subject:  
      Sent:     5/26/2009 12:33 PM
The following recipient(s) cannot be reached:
      'user name' on 5/26/2009 12:33 PM
            550 5.7.1 Unable to relay for user@domain.com


I have given him relay permissions to the SMTP connector so I believe he should be able to accomplish this.  

During my testing I created a test profile on another machine where i mimicked the same configuration. Test user is attached to local exchange account to company A and company B's pop 3 account is then added as an additional mail account.  Through the test account I am successfully able to send emails via the pop account but I am noticing on the receiving end the senders address is showing as user@companyA.com not company B.

Am I going the right direction in my configuration or is there a better way to accomplish this? I have previously been able to do this with exchange 2007, but am having difficulty doing it in SBS 2003.
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breynolds01Asked:
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ThaVWManCommented:
You need to check what account outlook is sending from when doing the Company B emails.  Since exchange is most likely the default account, when you go to send or reply to an email. outlook automatically selects that as the account it is going to send from.  So, this most likely answers the question as why the receiver for the test account messages is showing the wrong company domain.

You can see what account is being used at the top of the email, it should have a drop down that allows you to change what account outlook is going to use.
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breynolds01Author Commented:
I forgot to mention that... We are selecting the pop3 account (company B) when generating new emails
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ThaVWManCommented:
You said you have given him relay permission on the SMTP connector... what about in the Default SMTP Server itself?
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breynolds01Author Commented:
Yes I have, this is currently how I have it configured.
5-26-2009-3-17-36-PM.png
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ThaVWManCommented:
Ah... you dont have the users enabled.... Try unchecking the box that says allow all computers (Which is a good idea anyways), and then go into the users section and give that person rights there.  Having that check box checked can make it easier for spammers to use your server as a relay.
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breynolds01Author Commented:
I have tried it that way as well, but i will switch it back and report what i find.
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