I've reviewed the topics similar to the issue I'm having but I've yet to solve my problem. Been pulling my hair for over 10 days trying to fix this issue. Currently users within the LAN cannot use out of office or look up the free/busy time within Outlook 2007 and outlook 2010. But users can view this information by accessing the OWA site witin the lan. Users who also VPN in can also view the out of office info and Free/busy info. Whatever change I make users within the office cannot see the info. Here is my setup. I have a DNS entry for autodiscover that points to my CAS I have a dns entry for webmail that points to my CAS (our owa site is https://webmail.domain.com) I have a certificate with "webmail.domain.com", "autodiscover.domain.com" and "srvmail" (last is our exchange server host name) I do not get certificate issues. When I right click on my Outlook 2010 client in taskbar and run the "use autodiscover" test I get the following: Attempting URL https://autodiscover.domain.com/autodiscover/autodiscover.xml found through SCP Autodiscover to https://autodiscover.domain.com/autodiscover/autodiscover.xml starting Autodiscover to https://autodiscover.domain.com/autodiscover/autodiscover.xml Succeeded (0x00000000) My outlook 2007 / 2010 clients are set to use Exchange Proxy Settings with this as the URL : https://webmail.domain.com with NTLM authentication. Connect using SSL only. On my EMC when I right click the OWA or the Autodiscover folder I cannot browse, I get try using HTTPS error instead. -----> I'm not sure what else to try here. It's clearly a permission issue rather then a certificate issue ( or so i think). I get an error 401 with shell: [PS] C:\Documents and Settings\admin>test-outlookwebservices |fl Id : 1003 Type : Information Message : About to test AutoDiscover with the e-mail address admin@domain.com. Id : 1007 Type : Information Message : Testing server SRVMAIL.domain.local with the published name https://webm ail.domain.com/ews/exchange.asmx & . Id : 1019 Type : Information Message : Found a valid AutoDiscover service connection point. The AutoDiscover URL on this object is https://autodiscover.domain.com/aut odiscover/autodiscover.xml. Id : 1013 Type : Error Message : When contacting https://autodiscover.domain.com/autodiscov er/autodiscover.xml received the error The remote server returned an error: (401) Unauthorized. Id : 1006 Type : Error Message : The Autodiscover service could not be contacted. Any help is appreciated it. Thanks guys.