Question : SBS 2008: reverting from smart host/pop3 connector to exchange hosted email (DNS)?

Hello,
We currently have SBS 2008, which has been configured and working for many months using all standard SBS wizards, including “POP3 Connector” and “Smart Host for Internet”.  The current configuration is that the email and website are taken care of by 3rd party hosting company.  Therefore, our SBS server gets email via POP Connector and is configured to send out via our ISPs mail server, which we have to authenticate to.  

We need to switch from the current configuration to having email delivered directly to our SBS server, and sent from it just the same.  I would like to have you verify my gameplan, and have help with any missing or wrong steps.  Here are the steps I have outlined so far:

1) Log onto our hosting company, and change DNS records:
a) mail.myexternaldomain.com, change from ‘CNAME’ to ‘A Record’, and set address to external static IP address of our SBS server.> On our router, forward port 25 to internal SBS IP.
b) Edit current MX record from value 0 myexternaldomain.com to value 0 mail.myexternaldomain.com .

2) On SBS Server> SBS Console> Smart Host for Internet e-mail wizard> change from “I need to configure a Smart Host server for Internet e-mail” to “I do not need to configure…”

3) On SBS Server> SBS Console> POP3 Connector (What do I do with this? How do I remove? I don’t want to login to 3rd party mail.domain.com anymore?)

4) Contact the company that provides our internet/static IP and have them setup a reverse DNS entry with same info in step 1a.

Question 1:  Is the above plan of attack correct for SBS 2008 specifically?

Question 2:  Regarding step 1; all SBS wizards and SSL certificate I purchased/configured have been remote.myexternaldomain.com, which SBS seems to want to use.  Should the ‘mail.myexternaldomain.com’ be changed to remote.myexternaldomain.com?)

Question 3:  Regarding step 3 above, I don’t know what I’m supposed to do with that?

Question 4:  To send email historically we have had to send thru and authenticate with our ISPs SMTP server.  How does that play into the new configuration?

Question 5:  Do steps from this article need to be done (starting services, etc?):
http://blogs.technet.com/b/sbs/archive/2008/09/19/how-to-configure-sbs-2008-to-host-pop3-imap4.aspx


Thank you very much for all your help!

Answer : SBS 2008: reverting from smart host/pop3 connector to exchange hosted email (DNS)?

In order:

#1: Right steps, wrong order. Here is what I would do.

a) Get the reverse DNS record done first. It won't hurt pop3 delivery or smarthost sending so might as well do it BEFORE you make the switch.

b) Add a SenderID/SPF record to your DNS server allowiing your public IP to send mail on your domain's behalf.

c) Run the smarthost wizard. You can send mail directly and still receive mail via pop3.  But sending mail directly will work best if you know your reverse DNS record is set and you've set up a SenderID record. Monitor logs and queues, send some test mails, make sure this is working.

d) Run the IAMW and configure your server to receive mail directly. It can be *configured* to receive mail directly and still use the pop3 connector at the same time. Test your server vy trying to simulate an email being sent directly. Since your MX recods will still have mail getting delivered to your hosting company, you'll have to use telnet to test. Plenty of tutorials on how to do this. USe a machine outside of your network for testing so you know your firewall works as expected, exchange response as expected, and you can get a real message to your server as expected.  There are also some web based tools that can test a specific IP (mxtoolbox.com had one last I checked) but regardless, KNOW your exchagne server can receive email before flipping the switch.

e) Now make that last DNS change, update the A and MX records to send mail directly to exchange..

#2: If you've purchased a certificate for remote.* then you should make sure your DNS changes and the address used in the IAMW above reflect that. Otherwise you'll have certificatre errors.  In short, don't use mail.*

#3: Since DNS takes time to propogate, leaving the pop3 connectors running for a few days is not a bad idea. When you are satisfied that all mail is now getting delivered via SMTP, simply use the pop3 wizard on the SBS console to remove all pop3 accounts.

#4: You'll discover if this is the case when you perform step c above. Hence the reason for testing and doing each step completely separately and not in one big bang. If your ISP connection is "business class" then you can probably make the switch without any intervention. Residential class connections may filter port 25, in which case you'll want to work with your ISP to get the appropriate ports unblocked and make sure you arent breaking any terms of service by standing up a mail server on your connection.

#5: Not for the type of switch you are doing. You'd follow those steps if you had a specific need to allow home uers access to their work mail...and even then I'd argue that there are better ways. But if that time comes, it'd be a separate EE question at that point. In short, not needed for converting from smarthost/pop3 to direct SMTP ingoing and outgoing.

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