Outlook Anywhere Help

Hi, i have an SBS 2008 server with Exchange 2007 installed. Now i enabled Outlook Anywhere in the Exch Console, and for the external URL (remote.mydomain.com), i purchased an SSL cert and got that installed successfully.

On my machine I am trying to setup an email account and i am getting a "The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."

I followed these steps for the Outlook 2010 configuration:

What i am missing?
Who is Participating?
Simon Butler (Sembee)Connect With a Mentor ConsultantCommented:
A CNAME is not suitable if you have a single name SSL certificate, as it will generate certificate errors. You need to use an SRV record.

That will need to point to remote.example.com.
Delete the CNAME.

Was the server setup by the SBS wizards? You shouldn't have done anything in the Exchange console and by default on SBS 2008 Outlook Anywhere is enabled.
I would disable Outlook Anywhere in Exchange 2007 console, wait 15 minutes for that change to be done by Exchange. Then run the fix my network wizard in the SBS console. SBS does things in an odd way and if you try and configure things outside of SBS it breaks quite badly.

Simon Butler (Sembee)ConsultantCommented:
Do you have Autodiscover records in your DNS?
Depending on the type of certificate purchased it will depend on what records you need.

Krishna PatilCommented:
Can you post output of "Get-OutlookAnywhere" command?
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Cobra25Author Commented:
i created an autodiscover cname and pointed to the remote A record. Still waiting for it to propogate.

I purchased just a 1 domain SSL cert from godaddy.
Cobra25Author Commented:
[PS] C:\Windows\System32>Get-OutlookAnywhere
WARNING: IIS://FS2.miller.local/W3SVC/1/ROOT/Rpc was not found. Please make
sure you have typed it correctly.

ServerName                 : FS2
SSLOffloading              : False
ExternalHostname           : remote.****.com
ClientAuthenticationMethod : Basic
IISAuthenticationMethods   : {Basic}
MetabasePath               : IIS://FS2.miller.local/W3SVC/1/ROOT/Rpc
Path                       :
Server                     : FS2
AdminDisplayName           :
ExchangeVersion            : 0.1 (8.0.535.0)
Name                       : Rpc (Default Web Site)
DistinguishedName          : CN=Rpc (Default Web Site),CN=HTTP,CN=Protocols,CN=
                             FS2,CN=Servers,CN=Exchange Administrative Group (F
                             YDIBOHF23SPDLT),CN=Administrative Groups,CN=First
                             Organization,CN=Microsoft Exchange,CN=Services,CN=
Identity                   : FS2\Rpc (Default Web Site)
Guid                       : e87fce20-5769-4223-8b4e-0012db9726a0
ObjectCategory             : miller.local/Configuration/Schema/ms-Exch-Rpc-Http
ObjectClass                : {top, msExchVirtualDirectory, msExchRpcHttpVirtual
WhenChanged                : 2/5/2014 12:21:31 AM
WhenCreated                : 12/22/2010 2:27:40 PM
OriginatingServer          : FS2.miller.local
IsValid                    : True
Krishna PatilCommented:
*Instead of creating use profile manually, please try following thing.
--> Login to machine by any user who has mbx on exchange 2007.
---> open outlook, let outlook do auto discovery.
---> If OL gets opened successfully, check the "Connection" setting.

 if this does not work, please reply for following questions

1) Do you have single exchange 2007 server?
2) Does all roles installed on same server?
3) What are SUBJECT ALTERNATE NAMES (SAN) in the certificate , that you got from godaddy?
  Does it include, external, internal,auto discover name of exchange server?
Cobra25Author Commented:
Simon - thanks for the tip, i added a SRV record instead of CNAME. Outlook anywhere was on by default.

Manoj- 1 exchange server, all roles on it, no other SAN (it is for 1 domain)
Krishna PatilCommented:
Automatic profile creation is failing?
Cobra25Author Commented:
i am getting that error message. Nothing happens after.
Simon Butler (Sembee)ConsultantCommented:
Did you run the fix my network wizard in the SBS console? I suspect this is due to a change being made outside of the SBS system and the wrong web site is being used.

Jeffrey Kane - TechSoEasyPrincipal ConsultantCommented:
Make sure there is no wildcard (*) CNAME record in your domain's DNS. If there is, remove it.

If you continue to have issues, use https://testconnectivity.microsoft.com/ to resolve them.

Cobra25Author Commented:
Simon - i disabled and enabled the outlook anywhere and ran the fix my network wizard.

I am still getting the same error though when trying to connect. On a side note, the get-outlookanywhere does not return any warnings as it did before
Cobra25Author Commented:
Jeff - i ran the RPC over HTTP test on the test microsoft site, everything was successful.
Cobra25Author Commented:
Retested it now, and its working.

Thanks Simon!
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