Exchange outgoing mail won't send

[Leozack]

I'm frustrated and out of ideas here.
On a server at home SBS2003 has exchange set to retreive po3 mail from 2 sources (isp and website host). SMTP connectors sends outgoing mail to smtp.isp.com and outgoing auth is set to anonymous though I'm sure it should be required. All works ok it seems.

The problem is on a different server on another site. SBS2003 wants changes to collect pop3 mail for a number of users, and send all pop3 mail back through their emailhost's SMTP server which is mail.emailhostname.com. The problem is nothing is getting out, and if you look in exchange manager under servers/servername/queues you see "smallbusiness SMTP connectiong - mail.emailhostname.com (SMTP connector) with a load of messages in the queue and state set to retry. Forcing connection makes it go active but quickly goes back to reply.

I've tried adding outbound authentication both in the delivery properties of "default SMTP server" and under advanced properties of "smallbusiness SMTP connector" (using the login@emailhostname.com/password from a random user) but still no luck!

I've also added external DNS servers in delivery properties of "default SMTP virtual server" on the advanced screen pressing configure, and I added mail.emailhostname.com under 'smart host' in that same advanced screen from delivery properies of "default SMTP virtual server".

So I'm out of ideas but getting to the point where I'm seriously configuring things away from the SBS2003 default.

What must someone do just to get clients using outlook (who were previously using outlook to check pop3 mail and send via emailhostname.com using their login for authentication) to use exchange while exchange gets their email for them (this bit is working fine) but exchange also sends it (via mail.emailhostname.com)?

I need to sort this ASAP so they can do email :/

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Leozack

MakeUniverse($infinity,1,42);

 

[Leozack]

I'm pretty desperate for comments here cos It's an ASAP situation and they can't send email.

The situation has now changed - I found the email server in question from the hosts (not ISP) was using nonstandard format - aka port 26 not 25 for outgoing mail and a + in the username instead of an @.

I've removed the outgoing authentication from the "default SMTP virtual server" as it made no difference - and changed the port from 25 to 26 - then with correct outgoing authentication in "smallbusiness SMTP conenctor" it the queue empties and state is active/ready! Woo!

Now ... the NEW problem is instead of the queue issue, and no mail sending and nothing bouncing back - emails from clients are bouncing back IMMEDIATELY (so fast I thought it was from the exchange server not the emailhost server, but it seems not, since if I brake the authentication it doesn't bounce back and the queue jams again). The messages is :

There was a SMTP communication problem with the recipient's email server. Please contact your system administrator. <emailhostname.com #5.5.0 smtp;550-Verification failed for <clientemail@emailhostname.com>>

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Leozack

MakeUniverse($infinity,1,42);

 

[Leozack]

OK turns out NONE of that monkeycrap was necessary - could I find ANYTHING online or ANYONE who knew? No. Why? Because everyone is dealing with exchange in full blown email server mode with network clients and email users.

All I was doing was getting exchange to check pop3 email and deliver it to network clients and send it back again. The problem was simple the email alias for the user accounts - or rather - the email addresses tab showed their primary SMTP was firtlast@domain.com and firstlast.domain.local. Their network names are indeed firstlast but their domain.com emails are just first@

So - the fix? Change the exchange recipient policy to be %g@domain.com which give them first@domain.com (%g is "given name", aka first name) instead of just domain.com which gave them firstlast@domain.com. Once that was done - outgoing mail sends fine - no need for outgoing authentication stuff - it's obviously verifying using the primary SMTP address for that user object in AD.

Sorted! Take heed all SBS/exchange pop3 users

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Leozack

MakeUniverse($infinity,1,42);