<div>
So an external user user@domain.com is trying to send to an internal user of plee@cmitsolutions.com?<br />
<br />
Is the recipient policy up to date? Can you try telnetting to the server locally as a test as per the instruction below?<br />
<br />
telnet locahost 25<br />
helo<br />
mail from:user@externaldomain.c<wbr />om<br />
rcpt to:user@localdomain.com<br />
data<br />
moo<br />
.<br />
<br />
Can you paste the results of this here?
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<div>
telnet 192.168.2.* 25<br />
mail.domain.com Microsoft ESMTP MAIL Service, Version: 6.0 ready at Tue, 22 Jul 2008<br />
helo<br />
250 mail.domain.com Hello []<br />
mail from:plee@cmitsolutions.co<wbr />m<br />
501 5.5.4 Invalid Address<br />
<br />
domain.com is the internal domain, cmitsolutions.com is the external recipient. <br />

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<div>
Ok so there is something not quite right on yuour Default SMTP Virtual Server.<br />
<br />
Can you Disable your current Default SMTP Virtual Server and create a new Virtual Server with the default settings. Use Port 25 and the default IP address for the new Virtual Server. If this works then we have the email flowing again and can then look at SMTP SSL/TLS.
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<div>
I just turned off anonymous SMTP access (!) and now i get this output:<br />
<br />
220 mail.gutenbergpr.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.395 ready at &nbsp;Tue, 22 Jul 2008<br />
helo<br />
250 mail.domain.com Hello [192.168.2.60]<br />
mail from:user@domain.com<br />
454 5.7.3 Client does not have permission to submit mail to this server.<br />
<br />
<br />
Connection to host lost.
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<div>
This is the output after I replaced the existing SMTP server with a new one, configured with defaults. <br />
<br />
220 sbs.domain.local Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at &nbsp;Tue, 22 Jul 2008 17:29:32 -0400<br />
helo<br />
250 sbs.domain.local Hello [192.168.2.60]<br />
mail from:user@domain.com<br />
250 2.1.0 user@domain.com....Sender OK<br />
rcpt to:plee@cmitsolutions.com<br />
550 5.7.1 Unable to relay for plee@cmitsolutions.com<br />
<br />
<br />

</div>


<div>
It's going to be down to the relay and access permission on the Default SMTP Virtual Server.<br />
<br />
Ensure that it's not limited by IP.
</div>


<div>
Where can I see these settings? I'm trying to learn as much as I can about this, so tell me as if I was drooling copiously onto my keyboard. 
</div>


<div>
correct me if i'm wrong, but won't this allow anyone to relay on my SMTP server?
</div>


<div>
No it wont' it's actually a tight configuration. It will only aloow incoming mail for your domains.<br />
<br />
As we are only accepting the list below, and they are empty, no-one other than your users can send email.
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<div>
Are you running some antispam software such as Sophos puremessage or Symantec Mail Security., <br />
<br />
If so you have to specify the relay servers as allowed, or they get blocked by the software when trying to deliver mail. <br />
<br />
Also, have you added @cmitsolutions.com to the recipient policy, but not ticked the generation rules tick box? That box is not just to give everyone a mail address @cmitsolutions.com - it also sets the relay permsissions in Exchange and is a common mistake. <br />
<br />
Just a couple of ideas/<br />
<br />

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<div>
<div class="content wysiwyg-content">
I am trying to get SMTP-SSL running on an Exchange 2003 server (SBS 2003 FYI) and cannot seem to succesfully authenticate and send a message. When i run the zoneedit SMTP test i get this output. <br />
<br />
OK, connected to mail.gutenbergpr.com...<br />
&lt;&nbsp;220 mail.domain.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at &nbsp;Tue, 22 Jul 2008 16:44:14 -0400 <br />
&gt;&nbsp;HELO edit.dnsvr.com<br />
&lt;&nbsp;250 mail.domain.com Hello [64.85.73.124]<br />
&gt;&nbsp;MAIL FROM:&lt;user@domain.com&gt;<br />
&lt;&nbsp;250 2.1.0 user@domain.com....Sender OK<br />
&gt;&nbsp;RCPT TO:&lt;plee@cmitsolutions.com<wbr />&gt;<br />
&lt;&nbsp;550 5.7.1 Unable to relay for plee@cmitsolutions.com<br />
<br />
<br />

</div>
</div>


I am trying to get SMTP-SSL running on an Exchange 2003 server (SBS 2003 FYI) and cannot seem to succesfully authenticate and send a message. When i run the zoneedit SMTP test i get this output. 

OK, connected to mail.gutenbergpr.com...
< 220 mail.domain.com Microsoft ESMTP MAIL Service, Version: 6.0.3790.3959 ready at  Tue, 22 Jul 2008 16:44:14 -0400 
> HELO edit.dnsvr.com
< 250 mail.domain.com Hello [64.85.73.124]
> MAIL FROM:<user@domain.com>
< 250 2.1.0 user@domain.com....Sender OK
> RCPT TO:<plee@cmitsolutions.com>
< 550 5.7.1 Unable to relay for plee@cmitsolutions.com




Cannot send mail through Exchange 2003 SMTP server

Interactions between email servers and clients are governed by email protocols. The three most common email protocols are POP, IMAP and MAPI. Most email software operates under one of these (and many products support more than one).  The correct protocol must be selected, and correctly configured, if you want your email account to work.

Email Protocols

Exchange is the server side of a collaborative application product that is part of the Microsoft Server infrastructure. Exchange's major features include email, calendaring, contacts and tasks, support for mobile and web-based access to information, and support for data storage.

Exchange

Small Business Server (SBS) is a line of server operating systems targeted at small businesses by bundling the operating system with a number of other Microsoft products that would normally need to be purchased or licensed separately. The most notable inclusions are Exchange, SQL Server, SharePoint and ISA/TMG (Microsoft's firewall and proxy server).