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Help with Upgrade from 2003 to 2008 Issues

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  • Help with Upgrade from 2003 to 2008 Issues

    I have an interesting scenario, and please forgive me, I am somewhat new to managing AD. I am running several Windows servers on a VMWare ESXi host. The Active Directory version is "44", which is Windows 2008's version. The Domain Controller is Windows Server 2008 Enterprise. There is a SQL 2008 Enterprise server also runnning on 2008 Server Enterprise. The Domain functional level is 2003, and the Forest functional level is 2000. The DNS service is running on a Windows Server 2003 Enterprise server. There is another Windows 2003 server that is hosting our website.

    I am trying to upgrade the DNS server (2003) to Windows Server 2008 Enterprise SP2 (not R2) (after taking a snapshot of course). The upgrade installs fine, but we start to get an error stating:

    [Microsoft][ODBC SQL Server Driver][SQL Server]Login failed. The login is from an untrusted domain and cannot be used with Windows authentication.
    I have rolled the DNS server back to the previous VMWare snapshot of Windows 2003, so we are working again, but I need to upgrade to 2008 soon for upcoming security requirements.

    What can I do to fix this? I have listed all of our servers and settings below for your convenience:

    Domain Controller - 2008 Enterprise SP2
    - Domain Functional Level - 2003
    - Forest Functional Level - 2000
    SQL 2008 Server - 2008 Enterprise SP2
    IIS - 2003 Enterprise R2
    Another IIS (being shutdown soon) - 2000 Advanced Server
    DNS - 2003 Enterprise R2 (this is what I am trying to upgrade to 2008 Enterprise SP2)



  • #2
    Re: Help with Upgrade from 2003 to 2008 Issues

    It would be worth reviewing the the LANman authentication level and ensure it is set to NTLMv2 with LM and NTLM negotiated. That may be the issue. Review Group Policy to see if this is already set. Windows 2008 is NTLMv2 only by default.