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Does it work to use Outlook Anywhere on the local LAN without changing any settings?

I don't have a problem making Outlook Anywhere work when the computer is off the LAN. However, when the computer is on the LAN I can't get it to accept the settings.

Is it possible that I need to reconfigure something in our SonicWall firewall/router? The domains used, and point to one of our WAN addresses. I'm guessing this is where the problem is?!

Update: The solution I've found so far was to create a DNS zone on our server for and then I created A records for "autodiscover" and "remote" that point to our server. I also had to create A records for and to ensure that we can still access our website from within our network. Does someone have a better solution or know of any other problems my "solution" might cause?

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up vote 3 down vote accepted

A better solution:

Create DNS zones for and Create an A record in each zone with no hostname and point it to your Exchange server.

Another option is to look into what it takes to enable NAT hairpinning. On Sonicwall firewalls, I believe you need to use the 1-to-1 NAT feature in order to enable this. So you would need an extra external IP address that you can give to your Exchange server.

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Our Exchange Server is an SBS 2008 box that hosts everything for the company. Would creating a 1-to-1 NAT cause some security issues? Also, we have four slow DSL lines, each with one external Class A IP address. I'm actually working on a solution where I'll be able to use two or three of our DSL connections to send and receive email instead of just one of them, as is the case now. We send a lot of emails with large attachments. – HK1 Feb 11 '11 at 0:33
SBS2008 creates an internal DNS zone during configuration named "" (if you accept the default settings) expilictly for internal Outlook clients and an A record is created for that zone that points to the internal ip address of the server. This is explicitly set up to allow internal Outlook clients to automatically discover the Exchange server internally. I've never had to set up or configure any additional DNS records to get Outlook configured automatically using Outlook Anywhere – joeqwerty Feb 11 '11 at 2:35
@HK1 - A lot of people seem to think public IP address means insecure. This simply isn't true. Just because you have a dedicated public IP address on that server, doesn't mean it can't be secure. Just configure your firewall to only allow traffic you permit. As for the 4 DSL lines, I'm lost on that. Getting a bonded T1 would be my answer...of course, I don't really do cheap solutions. I do solutions that work. – Jason Berg Feb 11 '11 at 2:57
@joeqwerty - I think you're mostly correct. A standard SBS2008 setup creates the records you need. I don't think a migrated setup does though, so there are situations where these records aren't in tact. – Jason Berg Feb 11 '11 at 2:59
I'm not sure that it doesn't. I've just completed two SBS2003 to SBS2008 migrations and that was the case in both migrations. – joeqwerty Feb 11 '11 at 3:28

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