Outlook OAB Syncing Through a Proxy

Add your CAS server name / OAB URL to the proxy Exclusions list

In the Group Policy - under Execptions I have put in the FQDN of the Exchange server and the OAB directory address.  I dosent seem to work.

I am wondering if Cached mode is conflicting?

Okay here is the test results from my test machine which has the GPO applied to it.  Does all that look correct?
Capture.JPG

Is that webmail.xxx.com name in your exclusions?
If you ping it internally does it resolve to the internal IP address of your CAS server?

what error do your Outlook clients get when trying to download the OAB?

I think you have lead me in the right direction.  Earlier all that I had was FQDN in the exception list.  I have since added the webmail.xxx.com/oab as well and things are looking all right now.  I'll test later today and see if everything is working.

I was able to ping both by IP and Server Name which resolved correctly.  If everything goes well tonight I'll close out the request tomorrow.

Thanks for your help MegaNuk3

No problem. Fingers crossed

What error were your outlook users getting out of interest?

It was

Microsoft Exchange offline address book
Not downloading Offline address book files. A server (URL) could not be located.
0X8004010F

So it still doesnt look like its able to download the address book.  When I got to clients Outlook and send/recieve - download address book I get an error.  - See the attached image.  

Any thoughts ?

Look at your proxy settings as per this article:
http://blogs.msdn.com/b/dgoldman/archive/2007/02/15/oab-downloads-fail-with-0x80190197.aspx

Well I changed the REGKEY on one of the XP Computers that was having the issue and it seemed to resolve the issue.  

Do you know if the BITS Key is already installed on Windows 7 Machines?  I ask because I don't see the issue with the W7 users.

Or compare the LmCompatability reg key of a W7 machine vs WXP then change the value on the WXP machine to match the W7 then reboot WXP machine and see if that also resolves the OAB download issue.

If your proxy exceptions/exclusions are set correctly then outlook shouldn't even be using the proxy. If your OAB URL is https://webmail.xxx.com/OAB/<GUID>... then adding webmail.xxx.com to your proxy exclusions should be sufficient.

It looks to me at least on the two W7 machines that I had access to, That that key was there, with a different value.  But it was there.

There were some BITS 2.0 updates for XP machines within the last year (I inherited the network and WSUS was not installed - I have made my way to July 2010 for updates in 3 months).  I am going to go ahead and accept your solution - because either way you were able to fix the issue.

What key was there? LmCompatability? Or lmcompat? What was the value set to?

UseLmCompat - with value data set to "2"

There are also 8-9 adidtional keys in the WIN7 than the Win XP
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This is what I meant by LmCompatability


Expand the following registry subkeys, and then view the value that is assigned to the LM Compatibility entry:
HKEY_LOCAL_MACHINE\System\CurrentControlSet\Control\Lsa\LMCompatibilityLevel

I checked two Win7 units - neither one of them had that key.  I had everything up to the LMCompatibilityLevel

Thanks for looking anyway