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Can't connect Outlook 07 to Exchange over VPN

Posted on 2009-05-07
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Last Modified: 2012-05-06
Hi,

hopefully someone can point out what I've missed with this. I had Outlook 07 connecting perfectly fine on my bosses home pc. There's a VPN link between the house and the office. I've added an entry to the host file on the client machine and it resolves correctly via name and IP. It has been running fine for months until today. Can still ping the exchange server by name and IP, can open up network shares on the exchange server (small biz 2003), yet outlook won't open. I don't get the option to work in offline mode and I can't create a new profile as it won't resolve to the exchange server and I'm a bit stumped on this. Is there something minor I'm missing?

Oh, also I've checked to make sure nothing else is using the same port as outlook. Everything else is working fine on the pc with regads to connection to the company network.
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Question by:the1paulcole
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by:Mestha
ID: 24328409
You shouldn't need a hosts file if the VPN is working correctly. That should be removed and the VPN configuration checked to ensure that it is giving the correct DNS information when you connect. Are you using the SBS system for VPN or something else?

It is almost certainly name resolution, because windows file shares will find the server on broadcast.

Simon.
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by:the1paulcole
ID: 24362559
I've checked DNS settings and nothing has changed with them (using the DNS servers of the ISP). The host file was necessary as Outlook previously wouldn't work without it. We are using Juniper Netscreen firewalls and the VPN connection is setup between these (1 in the office, 1 at the house). Name resolution appears to be fine as this client machine can ping both exchange server name and IP.
I've looked at the RPC registry entries to make sure these are all correct (as per MS article), repaired Office 07 and I still cannot get it to connect. I'm getting close to tearing my hair out with this as nothing to my knowledge has changed (especially server side). Is there anything else I can look at or any other suggestions?
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by:the1paulcole
ID: 24363546
Just a quick update, I can also get to OWA without any problems from the client machine by using the internal server name. If it's a DNS related issue, surely this wouldn't work?
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by:Mestha
ID: 24363827
If you are using http://host/exchange then it would fall back to broadcast to find that host.

You shouldn't be using the DNS servers of the ISP if the machines are members of the domain. The only DNS servers that should be used are the domain controllers, even over a VPN. That would mean you wouldn't need to use hosts files at all. I don't know how many VPNs I have deployed over the years, not one of them uses hosts files. I dislike hosts files with a passion, and believe they have no place in a production environment.

Simon.
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by:the1paulcole
ID: 24367097
I understand what you're saying, but I think I should have been clearer on the setup. The client machine is not on the domain, it's on a completely seperate small workgroup about 20 miles away and has a juniper firewall and is connected to the internet via SDSL. there's a lan-to-lan vpn setup between our office and this site. I'm not 100% on the setup as it was done long before I started at the company. I'm starting to think recent microsoft patching
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by:Mestha
ID: 24370403
I am not aware of any patches that would have caused problems.
If the machines are not on the domain then I would be using RPC over HTTPS exclusively. That will get round any name resolution problems because it only uses DNS and you can easily set that up so the names resolve correctly internally and externally.

Simon.
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the1paulcole earned 0 total points
ID: 24420649
Hi, an update on this is required. I'm back on site and looking at this again. Completely stripped off office and re-installed but still have a problem. I seriously don't think it's DNS as I've created a new profile using my own Exchange account and Outlook opens fine, connects to our Exchange server and pulls down my email. I've sent emails to and from and it works perfectly well. I just cannot seem to get it working for this one Exchange account and I'm completely baffled as to why. I've tried creating a brand new mail profile, yet it still throws up the error about not being able to connect to the server.

Does anyone have any idea why I can open up any other Exchange account from the same location and server, just not this one? Where or what do I need to be looking at as this is definite hair tearing out territory now!
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by:mle724
ID: 24864017
We're experiencing the same exact problem with a single user right now.  And up until today he was able to access Outlook fine via VPN.  We've done all the steps you did and got the same results.  My problem is, this particular person is traveling in other states at the moment.

Please let me know if you ever got this resolved and how.
Thanks
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