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Fresh SBS 2003 install not receiving external email.

Posted on 2008-11-18
Medium Priority
Last Modified: 2012-05-05
Just installed a new SBS 2003 server with SP2 (not R2) and I can't receive emails from external recipients.  Here's a list of what I've been able to figure out so far...

1. Internal email works fine
2. External sent from another SBS server reports error 4.4.7 could not deliver in time specified
3. Gmail returns NDR saying my server did not accept request to connect.
4. IntoDNS reports all is setup fine except the Reverse DNS (ISP doing that today)
5. I can NOT telnet in on port 25 from outside the LAN, but internally i get good response
6. I put server in Maintenance mode and reinstalled everything except Exchange.
7. All of the standard SBS ports are open and pointing to the server.
8. NSLookup using multiple name servers looks good.
9. OpenDNS reports the right IP in their cache for mail.mydomain.com.

What's strange though...I try accessing my OWA from off LAN and I get an actual box that pops up asking for username/password instead of the OWA login page (internall it works).  I try logging in using my admin or user account and I eventually get the following (401 Unauthorized. Your client does not have permission to get URL / from this server. ).  So now I'm wondering if I'm dealing with 2 separate issues, or one in the same.  I don't think the reverse DNS can be causing all of this, especially not the problem with the OWA.  But maybe I'm wrong.  I've poked around the SMTP Virtual server settings and everything looks fine (it's a fresh install).  I'm not sure if the problem is there because the internal telnet got a good response and internal email works.  I'm not as good with IIS so I don't know if the problem could be within there or not.  I also cannot remote into the server using TermServ.  When I call my ISP today I'm going to ask if they have any sort of weird settings on their end that may be blocking anything.  It almost sounds to me its a firewall blockage issue, but all my ports are open.  At this point I'm starting to go in circles so I decided it was time to post.  

Any ideas?  
Question by:onsitess
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LVL 12

Expert Comment

ID: 22984750

what errors do you have in event log application?
LVL 11

Expert Comment

by:Stephen Croft
ID: 22985301
two seperate issues here;

1) Port 25 not being open from outside. What firewalls do you have (Pix etc) in front of your SBS server? Have you opened up a "port" (ie a static NAT) from the outside to inside on port 25 to allow outside connectivity?

The OWA issue sounds like you are going to the wrong url, what url are you using? (i.e. https://server/owa or https://server/exchange)


Author Comment

ID: 22987316
Nothing in the Event Log.  I'm at a client site right now so I don't know the exact model, but my firewall is a mid grade DLink Wireless.  I have all the standard SBS ports opened up (SMTP, RWW, HTTP, HTTPS, VPN, RDP, etc...) and pointing to my server.  I'm using the URL http://mail.domainname.com/exchange to access my OWA.  Even if I just go to http://mail.domainname.com or mail.domainname.com/remote I get the same thing.  

However, at this point this might all be moot.  When I talked to my ISP this morning to setup the Reverse DNS the guy said they are blocking most ports (it's a mom/pop wireless broadband company) so I sent him a list or ports to open up.  

So I guess put this on hold for the moment until I get the all clear from the ISP on their end.  I hope the problem is on their end because I'm going nuts if it isn't.
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Expert Comment

by:Adam Graham
ID: 22988091
It really does sound like a firewall/port blocking issue. Lots of ISPs are blocking on port 25 as standard practise now. If you can't telnet in from outside your never going to get any mail.

Does OWA/RWW etc work internally?

LVL 11

Expert Comment

by:Stephen Croft
ID: 22992636
If your ISP are blocking ports, they may not actually open them up. I've experienced this before with "Home Broadband" grade ISP's who don't believe you should be able to run a SMTP server on their line, and you should need a business broadband package to do so ;)

Good luck with it!

Accepted Solution

onsitess earned 0 total points
ID: 22994433
All is well in the world this morning.  They put me on an IP in their DMZ pool and everything started working.  Thanks to EE folks for their input, it's nice to know I can get a response in less than 1 hour.  For a second there I was starting to lose faith in my handy work =)  
LVL 11

Expert Comment

by:Stephen Croft
ID: 22994967
hehe always nice when it just "works" ;)


Expert Comment

by:Adam Graham
ID: 22996279
At least its working!


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