Outlook 2003 & Exchange via VPN

Discussion in 'Parallels Desktop for Mac' started by FireClown, Dec 14, 2006.

  1. FireClown

    FireClown Bit Poster

    My setup: Macbook 2Ghz Core 2 black, Parallels latest build 3036, shared networking, WinXP SP2 (fully patched), Windows VPN connection, Office 2003 (fully patched).

    My problem: Outlook is unable to see my Exchange Server via VPN. It works fine on my Windows PC. Entourage works fine on OS X, but that taps into Outlook web access instead of directly into the Exchange server (I think). Webmail works fine in Parallels Win XP. It's just the Outlook VPN that doesn't want to work. When I type in the server name and user name I get an error saying it can't find the server. I can get at the shares on the server just fine through Windows Explorer, so I know it's there and working.

    Anyone have any suggestions?

  2. dailo


    Try not using shared networking. When I'm at home on my wireless connection I can leave it on shared networking, however when I am plugged directly into the network at work I have to use the regular networking otherwise it won't let me login into the domain. I am not sure if this is the same problem for you.
  3. prock



    I have the exact same setup and software except I use bridged mode. My Outlook/VPN combo works fine so I know it can be done. Not sure if the networking mode matters but its worth a try. I also am NOT running the latest beta build but 1970 which I think is the latest general release build.

    I would also make sure that you can get a VPN client to work on the Mac side when parallels isn't running.

  4. FireClown

    FireClown Bit Poster

    Funny you should mention that...

    I haven't been able to get VPN working in OS X at all and my IT department basically told me to buzz off since I'm using a Mac. We use the Cisco client on the company PCs, but for home use we normally use the built-in Windows XP VPN client. I've tried the standard OS X vpn (both flavors) as well as Digitunnel and VPN Tracker. None of them work. At least, none of them work the way I've been setting them up. When setting the Windows VPN all I need to do is give it the VPN address and tell it to include the Windows domain (although if the domain isn't included as a separate box on login you can use username/domain instead).
  5. sfuller


    For VPN access under parallels, I've either been using the Cisco SSLVPN client (active X based) or the Cisco IPSEC vpn client (both running in XP). Both have worked fine for me so far. I've been able to access my exchange 2003 server via outlook with no complications.
  6. pshifrin


    You may need to edit your windows hosts file. Outlook probably can't resolve the NETBIOS name of the exchange server over VPN.

    Open C:\windows\system32\drivers\etc\hosts file with a text editor. (note this file has no extension)

    Add a line to the bottom. For example, if our exchange server was named "BABABOOEY" with an internal IP (at the office) of then the last line would read:

    # Copyright (c) 1993-1999 Microsoft Corp.
    # This is a sample HOSTS file used by Microsoft TCP/IP for Windows.
    # This file contains the mappings of IP addresses to host names. Each
    # entry should be kept on an individual line. The IP address should
    # be placed in the first column followed by the corresponding host name.
    # The IP address and the host name should be separated by at least one
    # space.
    # Additionally, comments (such as these) may be inserted on individual
    # lines or following the machine name denoted by a '#' symbol.
    # For example:
    # rhino.acme.com # source server
    # x.acme.com # x client host localhost BABAOOEY

    If you don't know the IP of the exchange server, ask the IT people or from inside the office,open a command prompt, ping the server and see what it is.
  7. FireClown

    FireClown Bit Poster

    Actually, I've already tried modifying the lmhosts file that we normally use. Our normal file just has the main servers listed, but I added the Exchange server to the list. That didn't work.

    I've also requested the Cisco client that we use on company PCs, but my IT department won't give it to me since I want it for my personal system, not a corporate one.

    I can get at Exchnage using Outlook Web Access, and my VPN connection in Windows seems to work fine of everything but Outlook. I even used the Remote Desktop Connection last night through VPN with no problem.
  8. milesce


    Outlook and Exchange 2003 doesn't rely on lmhosts or netbios names. It is, however, dependent on the right DNS entries or what is in your hosts file.

    Check and make sure at the command line you can

    ping hostname
    ping hostname.company.com

    While you are logged into the vpn. I'm was using outlook 2003, just upgraded to 2007, under parallels.
  9. petieg


    Outlook 2003/Exchange 2003

    Why not see if you co. is using RDP over HTTP -- this puts everything over port 80 thus no VPN required. That's the definitive for my using either product!!!
  10. FireClown

    FireClown Bit Poster

    I am getting confusing results with pinging. If I ping the server I get a 63.xxx.xxx.xxx address. The IP address I'm used to using is 10.2.xxx.xxx. In fact, I get 10.2.xxx.xxx for the other server. When I ping by the 10.2.xxx.xxx address I'm used to using I get no results. Conversely, if I go into IE and use either the server name or the 10.2.xxx.xxx IP address I find the server.

    I'll play with the hosts file and see if that does anything for me.
  11. darkone


    thats RPC over HTTP
  12. FireClown

    FireClown Bit Poster

    Bingo! Once I added the entries to the hosts file it worked.

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