SmarterMail and SBS 2011
Question asked by Case Price - 6/16/2015 at 1:22 PM
Unanswered
I am trying to find out if anyone has experience getting setup with SmarterMail running on a 2011 SBS box with Exchange. I understand the ideal would be to preserve the SBS default directory (and all the SBS related services/features) and create a virtual directory for SmarterMail to operate. But it seems the newer versions of SmarterMail no longer work under a VD and need to be established as their own IIS site. The client has another domain being serviced by the Exchange server and doesn't want to change those employees from the current setup but has a need to host email for other (lots of them) employees under a different domain. Is there a clean way to setup SM with alternate ports and still retain the SBS default site so all features remain working? Any guidance would be helpful. 

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Bruce Barnes Replied
PORTS cannot be shared on the same IP ADDRESS.

So long as you setup SmarterMail on a separate IP address, you should be able to make it all work together.
 
Remember, whether you have a public IP address on the SBS server, or you are running a STATIC DHCP address and using NAT and mapping to a public IP address via your router or firewall, you must have a separate PUBLIC IP address as well.
Bruce Barnes
ChicagoNetTech Inc
brucecnt@comcast.net

Phonr: (773) 491-9019
Phone: (224) 444-0169

E-Mail and DNS Security Specialist
Network Security Specialist

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Steve Reid Replied
I think you should run Smartermail on a different server. Smartermail deserves it's own server, especially one that is not also running another email server.
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Case Price Replied
Hi Bruce, I was hoping you would reply. I've read many posts and have always felt your knowledge of SBS is "spot on" in the ST forum (and maybe some external ones like experts-exchange.com). Normally, I would never try to do this type of setup and am fully aware SBS loves to "rule the world" when it comes to the network but was hoping there would be some way of getting it worked out without straying too far off course SBS setup wise. I know SBS only supports 1 NIC so I'm guessing the additional IP would be assigned to the single NIC and my router (dual WAN unit) has been configured with separate public IPs with those IPs having been assigned to their respective FQDNs (IP 22.22.22.22 goes to mail.domain.com and 22.22.22.23 goes to mail2.domain.com). I would then bind the 2nd private IP address to port 80 and 443, forward those ports for the WAN2 connection to that private IP, and test. I've read lots of posts about folks trying to do this and it seems it can be riddled with issues...any other advise/insight you could provide would be greatly appreciated.
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Case Price Replied
Thanks Steve and I totally agree with you...super appreciative for your insight. I was hoping to avoid that expense for the client but understand SBS is a beast when it comes to "playing nice" with others.
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Bruce Barnes Replied
Case: The only other thing I can think of is to make certain that SBS is not set to monitor all IP addresses.

I've frequently seen installations where IIS, or some other service is bound to a WILDCARD IP address and not to a stated, or individual, IP address.
Bruce Barnes
ChicagoNetTech Inc
brucecnt@comcast.net

Phonr: (773) 491-9019
Phone: (224) 444-0169

E-Mail and DNS Security Specialist
Network Security Specialist

Customer Service Portal: https://portal.chicagonettech.com
Website: https://www.ChicagoNetTech.com
Security Blog: http://networkbastion.blogspot.com/

Web and E-Mail Hosting, E-Mail Security and Consulting

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