Outlook 2003 over HTTP connection problems

Posted on 2011-04-28
Last Modified: 2012-06-21
Hi guys,

Here is a weird problem that we're having...

We have 2003 x64 server that people use as a terminal server, everyone has non-cached Outlook 2003 profile, we dont have our own Exchange and are using outsourced one via HTTP.

Everything worked perfectly for quite a while - 6 months at least. Then one day - we started getting Exchange is unavailable message occasionally. Message gives options to Retry, Work Offline or Cancel - Retry never works. The only way around is to keep closing the Outlook and starting again then eventually it will let you login.
Sometimes it lets you login right away without any problems though.

Im my investigation i noticed that when i create Outlook profile in an account of brand new user or a user who wasn't setup with Outlook before - it works perfectly, just like it worked before the whole thing started.
If i delete existing account profile, create a new one and configure Outlook again - it works crappy as it was with old profile.

Most have Outlook setup on their local machines and no one experiences any problems there

Let me know what you think
Thanks !
Question by:raymondhlee
    LVL 12

    Accepted Solution

    you can try running a test @ and post the results, more it seems to be more of a connectivity issue more than any Exchange issue

    Author Comment

    Thanks for the link - everything is OK there, works perfectly... But Outlook is still screwing around :(

    One of my thoughts was that it might be something with tcp/ip - but then it'd be screwy for everyone with no exception

    Must be something with Outlook...
    LVL 26

    Assisted Solution

    Can you share the details about the "Connection_status" on the working and non-working machines\profiles

    >> Around the system's system-tray (clock)
    On the Outlook 2003
    Right-click --> connection_status

    Need to notice:
    > if the problematic users are atleast trying to use https or summarily failing back to tcp\ip?
    > what is the servers/URLs the working server is connecting to?
    > when you access the same url @ the working and failing machine is that works fine (or any certificate error)

    Author Comment

    When it works it looks and works just like any other working Outlook.. connection status says Online and it operates 100% normal

    I tried to see what's going on using Network Monitor - not a pro at this but looks like at some point communications just stop between Exchange and the computer that tries to connect, basically it ends with either of them sending a packet and there is no reply back

    One of suspicions i have is NIC - but why would some profiles work without any problems then? I got a new one and it's just a matter of putting it in
    LVL 26

    Assisted Solution

    On the server IIS you have anything defined?

    From the working and failing clients:
    A) name resolution is same?
    ping e2k3-server-url (returns the same ip-address?)

    b) https://e2k3-server-url/rpc/rpcproxy.dll are showing the blank page?

    Note:Check for any IExplore proxy settings on the working and failing clients

    Author Comment

    a) yep all have the same thing going on
    b) gives me an option to login, after i do it then goes blank

    weird part is that it's just random - sometimes it connects right away and sometimes you need to go through those connection error couple of times before it actually connects

    I will put a new NIC in on the weekend and let know how that went

    Author Comment

    after installing new NIC it got a little better - not even sure that it was NIC that did this... now almost always opens from second try if it didn't work the first time

    thanks for the help guys

    Author Closing Comment

    Did not fix my problem but some good troubleshooting suggestions

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