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  • Outlook Anywhere

    I'm sorry if this is a repeat topic. I chcked all the SBS 2008 posts and didn't find anything.

    Here's the situation: I recently installed a SBS 2008 server at work. Exchange has been configured and I've got some mailboxes set up. Exchange works great in house and with the VPN. OWA and Remote Workspace are also working fine. Outlook Anywhere, however, refuses to work.

    I am currently trying to get Outlook anywhere to function using HTTP. I'm hoping to move to HTTPS, but we've already got an SSL based VPN in place that is using port 443, so it might not be possible to use HTTPS for Outlook Anywhere.

    When I set up Outlook on a remote system, I choose to install an Exchange server, put in the local FQDN (server.domain.local), enter the username, then click More Settings. I hop over to the Connection tab and check the box for connecting to Exchange with HTTP. I set the proxy settings to point to our remote domain, select HTTP before TCP/IP on fast and slow networks, and since I'm using HTTP, set NTLM Authentication.

    Wehn Outlook opens, it asks for my username and password. I supply correct credentials, but it just keeps asking for my username and password in an endless loop.

    I have confirmed that when I browse to http://domain.com/rpc/rpcproxy.dll I can enter my username and password and be presented with a blank screen. This would indicate to me that the connection to the server is good. I'm thinking that either Outlook is using a different connection or perhaps it is unable to resolve the internal FQDN of the exchange server once it hits rpcproxy.dll.

    I'm been pulling my hair out over this for days and I just can't find a workable solution.

    I'd greatly appreciate any ideas anyone might have.

  • #2
    Re: Outlook Anywhere

    Are you currently doing this with https or http? If HTTPS did you install the cert Correctly?

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    • #3
      Re: Outlook Anywhere

      So, we ended up scrapping the project. I was never able to get Outlook Anywhere working over HTTP. I did a test using HTTPS and that actually worked just fine. Because of that VPN in place though, we couldn't go with HTTPS because the finance people didn't want to get a second external IP.

      We ended up just using the VPN for Outlook access supplemented by OWA.

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      • #4
        Re: Outlook Anywhere

        Could well be a firewall issue, according to technet some firewalls have issues with the NTLM traffic so will only work with Basic Authentication, which is a very bad idea if you are not using HTTPS obviously.
        BSc, MCSA: Server 2008, MCSE, MCSA: Messaging, MCTS
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        Cruachan's Blog

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        • #5
          Re: Outlook Anywhere

          Originally posted by wvoorhees View Post
          So, we ended up scrapping the project. I was never able to get Outlook Anywhere working over HTTP. I did a test using HTTPS and that actually worked just fine. Because of that VPN in place though, we couldn't go with HTTPS because the finance people didn't want to get a second external IP.

          We ended up just using the VPN for Outlook access supplemented by OWA.
          Why would a VPN use 443?
          TIA

          Steven Teiger [SBS-MVP(2003-2009)]
          http://www.wintra.co.il/
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          Iím honoured to have been selected for the SMB 150 list for 2013. This is the third time in succession (no logo available for 2011) that I have been honoured with this award.

          We donít stop playing because we grow old, we grow old because we stop playing.

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          • #6
            Re: Outlook Anywhere

            We have the SonicWall SSL VPN 200. It uses SSL to create the VPN tunnel. The biggest advantage of this is that users can connect without specialized software from any web browser that supports SSL. It's a neat little device, but it does tie up 443.

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