Outlook2003 - 550 Relay Denied when sending emails (receiving is OK)

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Jul 28, 2006
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Hi Everyone... I'm lost and need a little guidence.
Currently what we have set up in our organization is:
Server = Win2K SP4 & Exchange2003
Client = Outlook2003
Inside our office my users connect to the Exchange2003 server by directly connecting to the Exchange Server which works quite nicely.

Outside of our office (on the road, from home) my users will use Outlook2003 to connect to our e-mail remotely. But the problem is that they can only recieve.....they can not send. If they attempt to send they get this error message as soon as they hit the send/recieve button:
The following recipient(s) could not be reached:
'(e-mail address removed)' on 7/28/2006 9:46 AM
550 (e-mail address removed) ...Relaying denied
Now I have checked my settings in the Account Settings.
- My POP3/SMTP have the same IP address of our External Firewall for the incoming/outgoing mail server.
- I click "test account settings" and everything checks out 'OK' AND it sends me that Outlook test message to prove its working.
- Under 'More Settings/Outgoing Server' I have chosen the option to log into receiving server before sending.

And if that doesn't do it for you, here's a little extra info:

1. If I connect a laptop inside our network and use the POP3 account settings I can send to everyone within the office. But if I attempt any outside email address I get the error stated above.

2. E-mail coming into our organization doesn't get sent directly to Exchange2003. It's first sent to "Syamantec SMTP E-mail Scanner" (on Port 25) which is then scanned for SPAM/Viruses then it is forwarded to Exchange2003 on Port26.
(I did attempt to setup a Firewall rule to allow Port26 open directly to Exchange2003, but when you configure the Outlook2003 client for Port26.... the test will come back with an error)

3. We use a Sonicwall Firewall Pro 4060


Thanks for anyone that can help. I'm not sure where the problem is. Is it a relay issue on the server that I have to configure?

Thanks,
Josh
 

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