How to setup Outlook Anywhere on Exchange 2010?

Hi There,

How exactly would I go about setting up Outlook Anywhere on our new Exchange 2010 server to help users avoid having to VPN to the Exchange Server just to get mail (via Outlook).

We have OWA working, and it works fine without any issues.

Also, to setup Outlook Anywhere, it is absolutely necessary to have an SSL certificate from a CA. Will Outlook Anywhere function without an SSL certificate?
Who is Participating?
Alan HardistyCo-OwnerCommented:
You will need an SSL certificate for Outlook Anywhere to work.  Please read the following MS article for details:
As long as you have setup Autodiscover in your Domains DNS records and have a Valid SAN / UCC SSL Certificate installed, it should work happily.
GenBayerAuthor Commented:
Can you please provide me with some more info on how to properly setup Autodiscover to get OA working.

Also, any suggestions on a place to buy an SSL Certificate?
Alan HardistyCo-OwnerCommented:
Autodiscover requires you to setup an A record in your Domains DNS with the name autodiscover which points to your server's IP Address:
Hostname     Type     Result
autodiscover    A         Your IP Address
That should allow everything to work for Autodiscover.
Cheapest palce to buy SAN / UCC certificate at present seems to be GoDaddy -
Names you need to include in your certificate are:
That should get you up and running if your server is configured happily.
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GenBayerAuthor Commented:
One or two more questions...

What happens if my email server is identified externally with a .net domain, but the default email address that Exchange is setup to assign to users accounts created is a .ca domain.

Thanks for all your help so far.
Alan HardistyCo-OwnerCommented:
The email addresses are not a problem, but you will need to include in the certificate too.
GenBayerAuthor Commented:
Would a Standard SSL Cert from GoDaddy do, or do I need a Deluxe Cert.?

Also, I'm a bit confused, most places I've checked stat that Exchange requires a UCC Cert and I think that is only available if you buy a Deluxe Cert.

So, just to be clear... Here are the domains we have:

The email addresses for all users is

Are you saying that I also need to add the domain to the SSL Cert. If that's the case, and since it's entirely different domain, would I not need to buy a Deluxe Cert.

Finally, one last question, once I've purchased an SSL Cert, can I add or remove domains to/from it?
Alan HardistyCo-OwnerCommented:
A standard Multiple Domain (UCC) certificate is sufficient - it works on my 2010 server.  5 name minimum, but if you need more than 5, buy a larger one.
Don't buy a wildcard certificate unless your internal domain name and external domain name are exactly the same.
If you buy a 5 domain cert and need to change domains, you can re-key the certificate to remove / add domains, but you can't exceed the number of domains for the certificate you purchased.  If you think you will need more domain names, then buy a larger number now, otherwise you will have to buy a new certificate with a greater capacity.
If you are not sure, buy a 1 year certificate then the cost will be kept low and if you need more later, the loss won't hurt as much!
Alan HardistyCo-OwnerCommented:
This question has been classified as abandoned and is being closed as part of the Cleanup Program.  See my comment at the end of the question for more details.
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