SBS2003 can't send email - Multiple SMTP connectors on SBS 2003?

New SBS2003.  Client existing email is hosted, so currently uses Outlook with POP3 to log into the remote server to send & receive email.  I installed a POP3 connector and used the credentials for BOB and can download emails fine.  I add another address in the connector for JOE and both are working.  Emails are going into the correct mailbox.  There is a one to one relationship with the pop account and the mailbox.  (Not a "catch-all" account).

Sending is another matter.  The outgoing SMTP connector needs authentication.  OK, I set up BOB in the smarthost, but JOE can't send email because he can't send as BOB.  Get it?  I added another SMTP connector with JOE's credentials, now JOE works, but BOB doesn't (error says BOB can't send as JOE).  I changed the SMTP Connectors to deny all users by default and allow only BOB or JOE depending on which connector... nope, still not working.

The idea is that the hosted email will remain safe in the event of a catastrophic failure of the Exchange server.  After all, these hosts have redundant servers, redundant internet connections, and it's cheap... why not use it?  The client just wants to be able to use group calendars and get all their email in one place - Outlook using Exchange.  Then in the event of a failure, he can still get individual emails by going to an Internet cafe and logging into his host's webmail service.

I thought maybe I could send directly using SMTP from the server, but email wasn't going through.  I later realized that reverse DNS lookups made me look like a spammer.  I tried adding an MX record for this server (using dynamic IP services).  When I look up MX records now, it shows up, but messages are still stuck in the queues.  I can clear the queues, but new messages still go into the queues and never leave.  Is it because of the dynamic DNS service?  Reverse DNS still doesn't match, so I'm being rejected as a spammer?  With one SMTP connector and one POP3 account everything works as I'd expect, but I need 12 email accounts.  

Please HELP!!!  How can I make this work and satisfy this new client?  

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Your arguments for using POP3 don't really standup.

Unless you are using a large hoster for POP3, then I would be surprised if they have redundant servers, internet connections etc. Considering that you can yourself up as a web host for like $30 a month on a single server you have no idea what the host is running on. They may not own any part of their service.

The argument for having the hoster as a backup service doesn't really standup either. In the event of a failure at your end, most email services will try and deliver email for 48 hours. Considering that I can have a replacement email service up and running in less than 4 hours, I am well within that window.

Hosters also have a habit of disappearing.

You will get a much better end user experience if you get email delivered by SMTP. The POP3 Connector will only collect email every 15 minutes by default. SMTP delivery will be instant.

For outbound email, does your ISP not provide an SMTP host that you can send email through?

Many major ISPs will block messages if you don't have a reverse DNS, you are on a dynamic IP address, your server's SMTP banner has an invalid domain in it.


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technoid-usaAuthor Commented:
We can debate the merits of hosted email, but whether or not the argument holds, this is what the client wants.  Their email has been reliable and consistent and they have no fear of their hosting company failing them.  Can anyone help me implement this?  The 15 minute delay is acceptable for incoming email.

It is something that you will have to take up with the hoster.

You cannot make Exchange use a different account for authentication depending on the sender. There is element of control based on the sender in Exchange - it is all based on the recipient.

Ask the hoster if there is a master account and password combination that will work. Depending on the way that they have deployed the email service there maybe something available.

Otherwise my second suggestion from the posting above - use the ISPs SMTP server - most of the time those don't require authentication.

technoid-usaAuthor Commented:
Thank you for your help.  I tried using the host's SMTP server with no luck - You mentioned using the ISP's SMTP server as a smarthost.  That did it.   I guess I was making it harder than it had to be by trying to setup multiple SMTP connectors.

Thanks again!

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