Solved

Outlook 2003  not connecting to Exchange 2007

Posted on 2011-03-19
17
465 Views
Last Modified: 2012-05-11
I have inherited a cobbled together network and need to integrate more computers from the company that took over the company.
It has an SBS 2003 server acting as domain controller,DNS server and DHCP server, a W2K serverused for SQL and an SBS2008 which is being used for Exchange.
This means that Exchange is on a different Domain.
The computers that were on site use XP / Outlook 2007 and connect to the Exchange server.

When adding computers (XP / Outlook 2K3) they join the domain ok but when connecting Outlook 2K3 to the Exchange 2007 mailserver they dont connect then when I select retry they do connect but are very slow and keep losing connection.
I think it may be a DNS problem but any suggestions are welcome.
Thanks in advance.
0
Comment
Question by:gogsck
  • 10
  • 6
17 Comments
 
LVL 3

Expert Comment

by:ServerGuyScott
Comment Utility
You'll have to gather some additional diagnostic data to determine what exactly the issue is.

If name resolution isn't working I would never expect the connection to be successful not to be intermittent. The case where it would be intermittent would be if you have multiple DNS servers defined on the client computer and one DNS server "knows" about the exchange server and one doesn't.

To test this out do a NSLOOKUP against all of the DNS servers you have defined for the client and make sure they return the proper IP address of the exchange server.

Is the exchange server sitting on a different network segment than the DC's and then the clients? If so perhaps there is a routing issue. Maybe do a tracert from the client machine to the exchange servers IP address. Then examine the route it's taking, does the route seem logical and from a network perspective is it the most efficient route (least hops?)

Also at the client open the mail profile, go to Change, More Settings and on the connection tab verify that the box for Connect to Microsoft Exchange using HTTP is UNCHECKED.

That is all that comes to mind given the information you've provided. Once you try some of the things out that I mentioned post back your findings and we'll go from there.
0
 
LVL 13

Accepted Solution

by:
connectex earned 500 total points
Comment Utility
That's a mess. It would be best if you got migrated entirely to SBS 2008. Also W2K server is no longer supported by Microsoft it should be replaced/upgraded to Windows 2008 or higher too. Otherwise the current configuration is going to be a nightmare going forward. Now is the time to put the work in so it's manageable going forward.
0
 

Author Comment

by:gogsck
Comment Utility
Hi,
Yes this network really is a mess. I support the IT services for company A that has just purchased company B and has moved into the premises of company B. Unfortunately company B is larger so the first priority is to migrate additional computers (and data) from company A to the network of company B network and get everything working.
Yes the ideal situation is to sort this mess out but at the moment the budgets will not allow this as the hardware also needs replacing.
For some reason all 3 servers have the 1st DNS entry (on the NIC) pointing to an extenal IP address and the internal IP addresses are 150.0.0.x  with a subnet of 255.255.0.0!
nslookup on the Exchange server (SBS 2008) cameback no server unknown and an ipv6 address.
Should the DNS settings on the Exchange /SBS 2008 box point to the SBS 2003 (DNS server)?
If I ping the exchangeservername from the SBS 2003 boxi get the host could not be found.
Do I need to add the exchangeservername to the DNS server on the SBS 2003 box?
0
 
LVL 13

Expert Comment

by:connectex
Comment Utility
DNS on SBS servers should point to themselves only normally. But I think you need to may need to point it to itself and the other SBS box too.
0
 

Author Comment

by:gogsck
Comment Utility
Hi,
I have changed the DNS on the SBS 2008 (Exchange server) NIC so that the first entry points to its self and the second entry points to the SBS 2003 server which acts as the DNS server for the LAN.
But nslookup on the SBS 2008 still says " server unknown".
Can I add the SBS 2008 computer to the DNS server on the SBS 2003?
0
 
LVL 13

Expert Comment

by:connectex
Comment Utility
Yes on both SBS server. So SBS 2003 would be itself and then SBS 2008. SBS 2008 would be itself and then SBS 2003. You may need to ping by full domain name. If that works then we can add all the domain names in the suffixes section of the DNS configuration page.
0
 

Author Comment

by:gogsck
Comment Utility
Both SBS servers have DNS pointing to themselves - now that I have changed them to do so.
Poth can ping each others IP address bot not the computername or computername.domain.
DNS servers are running on both SBS boxes.
0
 

Author Comment

by:gogsck
Comment Utility
An Update.
I have checked that in Outlook that connect via HTTP is not selected.
The problem is DNS on the SBS 2008 / exchange box.
I ran the Best Practice Analyser and said that the DNS client was not configured correctly but I cannot find out how to fix it.
Also if I run nslookup on the SBS book I get Server: unknown and an ipv6 address but no ipv4 address.
Is there anyone out there that can help me configure the DNS properly. I cannot use the built in wizards as somebody in there wisdom has configured the intenal network with an IP range of 150.0.0.x and a subnet of 255.255.0.0 !!!
Help please.
0
Top 6 Sources for Identifying Threat Actor TTPs

Understanding your enemy is essential. These six sources will help you identify the most popular threat actor tactics, techniques, and procedures (TTPs).

 
LVL 13

Expert Comment

by:connectex
Comment Utility
Can you post exactly what the BPA reports?
0
 

Author Comment

by:gogsck
Comment Utility
Hi,
BPA result.
DNS client not configured
The DNS client is not configured to point only to the internal IP address of the server. For information about how to fix network settings, see "Managing Your Windows Small Business Server 2008 network" at the Microsoft Web site (http://go.microsoft.com/fwlink/?LinkId=115881).

Everything I have read about this point to the reverse lookup zone but it appears ok to me.
The are 2 NICs one is disabled and all settings have been deleted the other nic has one DNS setting which is its own ip address
0
 

Author Comment

by:gogsck
Comment Utility
The actual nslookup error is:

C:\Users\server-administrator>nslookup
Default Server:  UnKnown
Address:  fe80::2a7b:6cb1:c7e7:3797
0
 
LVL 13

Assisted Solution

by:connectex
connectex earned 500 total points
Comment Utility
I'm using fake IPs and domains but hopefully you can see what I want you to setup.

Server 1
IP address: 192.168.0.2
Domain: domain1.com

Server 2
IP address: 192.168.0.3
Domain: domain2.com

Set the DNS on Server 1:
DNS Server 1: 192.168.0.2
DNS Server 2: 192.168.0.3

Set the DNS on Server 2:
DNS Server 1: 192.168.0.3
DNS Server 2: 192.168.0.2

Now from Server 1 attempt to ping Server 2 by FQDN 'ping server2.domain2.com'. If you get a reply then try only 'ping server2'. If the first ping works but the second didn't we need to add the domains suffixes. You do this under the Advanced->DNS tab. Click on Append these DNS suffixes (in order).

Set the DNS suffixes on Server 1:
domain1.com
domain2.com

Set the DNS suffixes on Server 1:
domain2.com
domain1.com
 
Now from Server 1 attempt to ping again. This time 'ping server2' should work. Let's see if that resolves you issue.

-Matt-
0
 

Author Comment

by:gogsck
Comment Utility
Hi connectex
Tried that but I get no respose from either server usind FQDN or servername. I added the DNS suffixes but still nothing. Pinging the ip addresses wors but nothing else.
I just tried something else.
I tried pinging a PC on the network by computername from both servers and got a reply to both of them.
Does that help or make things worse?
0
 

Author Comment

by:gogsck
Comment Utility
Hi,
I have just checked all reverse lookup settings against a known good SBS 2008 box that I installed and everything looks the same. But on the fault one when i tried nslookup i get.

> nslookup
Server:  UnKnown
Address:  fe80::2a7b:6cb1:c7e7:3797
DNS request timed out.
    timeout was 2 seconds.
*** Request to UnKnown timed-out
> server mailserver
DNS request timed out.
    timeout was 2 seconds.
*** Can't find address for server mailserver: Timed out
(I have changed the servename in this message - it is not actually called mailserver.)
But on the good one I get a response and the ip address returned.
I am wondering if I should delete all entries and try setting up the DNS from scratch?

Gordon
0
 
LVL 13

Assisted Solution

by:connectex
connectex earned 500 total points
Comment Utility
Well, I'm surprised nothing has worked yet. This is like a puzzle with a missing piece. I'd like to help more but there is only so much that can be done via EE. If you'd like you can check my profile for more information and we'll move forward offline.
0
 

Author Comment

by:gogsck
Comment Utility
Hi,

I have made a bit of progress. the client computers can now resolve the mailserver computername.
unfortunately I am not sure what made things work or if it was a combination of things. The servers still do not resolve each others names but I have now got outlook connecting to the exchange mailserver. I did add the mailserver to the host file on one computer that was timming out whilst trying to connect and it now loads outlook in about 1 second!

Thanks for all your help.
Gordon
0
 

Author Closing Comment

by:gogsck
Comment Utility
There was no real solution.
The best way forward for this network is to start again from scratch!
0

Featured Post

How your wiki can always stay up-to-date

Quip doubles as a “living” wiki and a project management tool that evolves with your organization. As you finish projects in Quip, the work remains, easily accessible to all team members, new and old.
- Increase transparency
- Onboard new hires faster
- Access from mobile/offline

Join & Write a Comment

Local Continuous Replication is a cost effective and quick way of backing up Exchange server data. The following article describes the steps required to configure Local Continuous Replication. Also, the article tells you how to restore from a backup…
Learn to move / copy / export exchange contacts to iPhone without using any software. Also see the issues in configuration of exchange with iPhone to migrate contacts.
In this video we show how to create a Resource Mailbox in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: Navigate to the Recipients >> Resources tab.: "Recipients" is our default selection …
To show how to generate a certificate request in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.:  First we need to log into the Exchange Admin Center. Navigate to the Servers >> Certificates…

771 members asked questions and received personalized solutions in the past 7 days.

Join the community of 500,000 technology professionals and ask your questions.

Join & Ask a Question

Need Help in Real-Time?

Connect with top rated Experts

10 Experts available now in Live!

Get 1:1 Help Now