Small Business Server Using Exchange and POP3 question

Here is the scenario:

I have a client in a small business server 2003 enviornment using outlook 2003 to receive their email via pop3 from a third party.
So the mx record is pointing to and the A record is pointing to's ip. The hosting provider is setup to receive email for Everything on that end is working as normal.

Right now the local sbs 2003 domain dns is setup as businessname.local according to small business server general standards.

One of our problems is that when we try to send email out through the exchange portion of the server we get kickbacks from the server saying delivery failure. Because outlook 2003 uses the "exchange" account as the default sending account. I know there is a registry fix to correct the problem but I do not want to have to use that method. See, sometimes users open exchange and forget to swtich to their pop3 account as default sending account. If they forget to do that then their email gets kicked back.

I dont want to have to use any hacks to solve this problem. From my understanding this is a known issue with SBS2003. Maybe there is a different way to set this up or use .com instead of .local as the domain?

Also, for redundancy, should I just setup 2 mx records 1 pointing to our server (primary) and direct all mail to the sbs server directly, and 1 pointing to the 3rd party email hosting (secondary) just in case our sbs goes down? (we live in FL and we have a lot of storms so I want maximum uptime without having to babysit issues)

and if I do it this way will it solve the problem above?
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You don't need separate POP3 accounts in Outlook to download your mail. You can use the POP3 connector which is included with your SBS. It goes off and checks the mail on the server and delivers it to the Exchange mailbox, making it arrive through Exchange. When sending out, you can either send out through DNS (the default option) or through a smart host on your ISP/host's SMTP servers. This can all be configured through the Connect to the Internet wizard. - Visual representation of Connect to the Internet Wizard
e.g. When asked to "Enable Internet E-mail", select that option and press Next. You are then asked whether you want to route mail via DNS or forward mail to an SMTP server. I recommend the latter if you have an ISP SMTP server to send mail through, simply because more and more postmasters of large companies are locking down their servers and DNS settings have to be just right for mail to go through. Enter the name of your SMTP server to send mail through in the box, press Next. You are then given an option to Use Exchange etc., make sure you check both so you can have the two MX records. Then go on to configure the POP accounts in the wizard.

If your users don't have an email address, you will need to add it to the Exchange recipient policy. (Note, in step 3, when told to create a new one, instead you should edit the properties of the existing Default policy, then open the Email Addresses tab and add the email address domain in the format through the tools there) That will give all user accounts an address.

Yes, you can set up multiple MX records as you say. Once can point to your server ( on an A record to your network's WAN IP address) and the other can point to your POP3 hosting company on the existing A record. I suggest you set the SBS up so it has first preference (lower cost) and the email host to have a higher preference. Provided you leave the POP3 connector enabled, you won't have any further problems. Also make sure that your router at the SBS end has port 25 forwarded to the internal IP of the SBS. The only thing the POP3 connector can't figure it is if an email is BCC'd to a user on the SBS from outside, it won't be able to find who to deliver it to in some cases because the BCC information is removed from the message when it gets to the POP3 host. This is why I suggest you have mail delivered direct to the SBS as first preference.

Just to add a little to the very comprehensive reply by tigermatt above:

There is another way to add redundancy to your mail server. Instead of using a POP service and then using a POP connector to pull down the mail, you can use an MX Backup service which is designed to do exactly this. In this case, you subscribe to a service (such as mailhop backup mx from - there are loads of others) and then modify MX records so your SBS server is the primary (first priority, ususally 10) and then set up the backup MX service providers server as the next (usually prio 20).

This way you don't need to use the POP connector, you don't have the administrative overhead to maintain a set of POP mailboxes in addition to your Exchange mailboxes, and you don't have the issue with BCC'd emails.

And as tigermatt mentioned, it us much nicer to have email running through Exchange directly - this is the way the system is intended to work and gives you a LOT more functionality (and performance) than using POP accounts in Outlook.


oriontech2Author Commented:
Thank you for the QUICK! response. I think it was less than 15 minutes, probably around the amount of time you took to write the response. Great job guys! Thanks for the assist Bud. Keep up the good work.
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