We have a single Exchange Server 2007 setup with Anywhere Access (RPC over HTTP) enabled. A 3rd party SSL cert is in place for Internet access: OWA, autodiscovery, etc.; everything seems to work OK. But, if an employee attempts to setup their Outlook 2007 (or 2010) from the WAN (their home, remote location), the Anywhere Access setup (Outlook Profile) gets stumped on the user's credentials and never connects nor configures properly. The same laptop, brought onto the LAN, configures immediately and Anywhere Access works for that user internally as well as from the WAN afterwards. It is just the initial setup that fails if attempted remotely. We try to configure everything internally prior to deploying laptops, but this is proving impractical. To add another oddity: some (a very few) successfully had their Anywhere Access setup remotely on their personal or company computer, and it just worked. But it is rare. Any ideas?

I would suspect that Autodiscover isn't configured correctly. If you aren't using autodiscover, but are configuring things by hand, then you are probably making an error with the authentication settings. Internally it works because autodiscover is correcting things for you. Autodiscover works slightly differently inside the network on the domain compared to externally. Run a test account through the Microsoft test site at http://exrca.com/ Simon.Simon Butler, Exchange MVP Blog | Exchange Resources | In the UK? Hire Me.

Hi Simon, It appears to be authentication related issue on the server side; however the original poster said some users can successfully had the Outlook profile setup, so the cause might be different and we need more information for analysis. @ PendumAdin, The connectivity test suggested by Simon is a useful tool, please try and let us know if there is any error. Besides, please provide the following information: 1. How does your user setup the Outlook? Type the E-Mail Account and then click Next in “Add New Account” box, or directly click Manually configure server settings”? 2. What User account does your users logon to windows when they try to setup the Outlook? A local computer user, or a domain user? 3. If it is a domain user account, has your user logon their laptop in your domain before? 4. Run the test below on the affected client with the steps exactly, and let me know the result: 1) Go to Control Panel->Mail->Show Profile, select “Prompt for a profile to be used”. 2) Launch Outlook with “Outlook /rpcdiag”; and then click “New” 3) Type the profile name->OK->Next; 4) In “AutoAccount Setup” box, type the email account you would like to setup; and then click Net. 5) If the issue occurs, capture a screenshot for the credential prompt box to see what server/service is require authentication; 6) Switch to Connection Status box, and let me know what server is trying to connect to. Note: you may run the test in your LAN: modify your local host file, point your Autodiscover URL (https://yourSMTPdomain.com/autodiscover/autodiscover.xml) to your external IP address of proxy server. Hope it is helpfulFiona

Any update?Fiona