Upgrading 2003 to 2008 R2 Advice

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    I have 10 servers, all currently 32-Bit 2k3 SP2 (2k3 native) as follows:

    On LAN:
    1 x DC, GC, File Server, BackupExec
    1 x DC, GC, Print Sercver, FSMO Roles
    1 x Exchange 2k3 (Standard SP2)
    1 x SQL 2005 (Standard SP3)
    1 x Citrix PS4 (Advanced)
    1 x Management (runs various applications – non critical)
    1 x Sybase (wish to do this last as it runs main client data database)
    1 x IIS Web Server (front end for Sybase client database)

    On DMZ:
    1 x IIS Web Server (running front end for Sybase client database)
    1 x Citrix Secure Gateway and Web Interface

    All servers are HP Proliant DLs (G4 and G5) and are all 64-Bit capable (although they run 32-Bit at present). They all have at least 12GB RAM and RAID optimised for their current use.

    The plan is to upgrade all servers to 2k8 R2, also taking Exchange to 2010 Enterprise at the same time. There are no plans to upgrade SQL from 2005 unless necessary at the present time.

    Citrix will be replaced by Remote Desktop Services in 2k8.

    What I’d like a little advice on is what the best order is to do the upgrades.

    I don’t have spare servers, but I can setup workstations running server software as temporary servers to help with upgrade.

    The work will be done out of hours (at weekends) so downtime is not an issue.

    My initial thoughts were to do the DCs first, followed by Exchange.

    Not sure how this will work with Citrix however – I cannot take Citrix down until I have got 2k8 RDS up and running (and staff briefed), but will Citrix PS4 run in conjunction with 2k8 DCs?

    Also, are there any problems running SQL 2005 Standard on 2k8 R2? Do I need to upgrade this as well?

    The Sybase and 2 x IIS servers will be done last – they run our business critical client database and web app and we need the developers in to perform this part of the upgrade.

    Any and all advice much appreciated.

    Thank you

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