Exchange 2010 CAS coexisting with OWA 2003 - HTTP 500 error

Posted on 2009-12-23
Last Modified: 2012-06-27
Exchange 2010 CAS and Exchange 2003 OWA server are co-existing. I've already specified the exchange2003URL parameter for the redirection in the exchange command shell. For exchange 2003 mailbox users, I can successfully login directly
But If I login via, I get redirected (exchange 2003 login prompt) then
when I enter the username\pwd, I get  500 Internal error at

If I enable Forms based auth on the exchange 2003 server, login works fine. I do not want to enable forms based auth because although this may
work fine internally, my owa machine is published on ISA 2006 for remote users and per Microsoft, " When ISA Server is being used to publish Exchange Web client access, forms-based authentication should only be configured on the ISA Server computer"

Another thing, why do I always need to enter the domain name \ username prefix when logging in to exchange 2101 OWA ?
In OWA 2003 I can simply enter the username and password, without the domain\ prefix.
Question by:anarine

    Author Comment

    Ok so for the second question, the solution was to select the default domain name in ESM --> Server configuration --> Client access --> Outlook web app --> auth settings.
    Still can't figure out the first problem with the redirection
    LVL 31

    Expert Comment

    The 500 error message you get from IIS is a very vague way of telling you that 'something went wrong at the server end'.  See if you can get more information by turning of the 'Friendly HTTP Errors' in your browser.  If you still don't see anything helpful, then it means that the error is caused by something that IIS doesn't know about, and you will have to look in the server's Event Logs.
    LVL 15

    Expert Comment

    On exchange 2003 Server on Exchange virtual directory remove SSL and FBA and set Integrated authentication and then try again.

    Author Comment

    I cannot remove SSL from the exchange 2003 frontend, since exchange 2010 CAS will not be able to redirect as it requires ssl target for redirecting..

    Accepted Solution

    The answer for the time being is to use the manual legacy redirect cmdlet: legacyredirecttype to manual

    Expert Comment

    I am currently running into the same problem.  Would you please explain how you use the legacyredirecttype to fix this issue.  As much detail as possilbe please.


    Expert Comment

    Hi there.
    use the following PS command

    Get-OwaVirtualDirectory -server Exchange2k10 | set-OwaVirtualDirectory -LegacyRedirectType manual

    Write Comment

    Please enter a first name

    Please enter a last name

    We will never share this with anyone.

    Featured Post

    Threat Intelligence Starter Resources

    Integrating threat intelligence can be challenging, and not all companies are ready. These resources can help you build awareness and prepare for defense.

    Suggested Solutions

    Resolve Outlook connectivity issues after moving mailbox to new Exchange 2016 server
    Check out this infographic on what you need to make a good email signature that will work perfectly for your organization.
    In this video we show how to create an Address List in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Organization >> Ad…
    To show how to create a transport rule in Exchange 2013. We show this process by using the Exchange Admin Center. Log into Exchange Admin Center.: First we need to log into the Exchange Admin Center. Navigate to the Mail Flow >> Rules tab.:  To cr…

    761 members asked questions and received personalized solutions in the past 7 days.

    Join the community of 500,000 technology professionals and ask your questions.

    Join & Ask a Question

    Need Help in Real-Time?

    Connect with top rated Experts

    8 Experts available now in Live!

    Get 1:1 Help Now