I have an old server that has custom software loaded on it that we can not reinstall. I have been able to upgrade it from Windows 2000 Adanced to Windows 2003 enterprise and just got acceptance for it at my work... so now I am looking to see if its possible to go further to 2008. That said, since R2 only works with 64bit, I am concerned that I'm about to hit the end of the line for this server. Is anyone aware of any tools, hacks, etc... supported or unsupported that may help in any way to port old installed software to Windows 2008R2? I have cloned my server onto VMware, so I can try things, blow it up, and easily recover. Any advice appreciated!

Hello, Upgrading from a 32 bit OS to a 64 bit one is completely not supported by Microsoft. Unfortunately, I don't know third party tools which may do that. You have to create a new server and try to migrate the roles / applications to it. This posting is provided "AS IS" with no warranties or guarantees , and confers no rights. Microsoft Student Partner 2010 / 2011 Microsoft Certified Professional Microsoft Certified Systems Administrator: Security Microsoft Certified Systems Engineer: Security Microsoft Certified Technology Specialist: Windows Server 2008 Active Directory, Configuration Microsoft Certified Technology Specialist: Windows Server 2008 Network Infrastructure, Configuration Microsoft Certified Technology Specialist: Windows Server 2008 Applications Infrastructure, Configuration Microsoft Certified Technology Specialist: Windows 7, Configuring Microsoft Certified Technology Specialist: Designing and Providing Volume Licensing Solutions to Large Organizations Microsoft Certified IT Professional: Enterprise Administrator Microsoft Certified IT Professional: Server Administrator Microsoft Certified Trainer

Hello, Upgrading from a 32 bit OS to a 64 bit one is completely not supported by Microsoft. Unfortunately, I don't know third party tools which may do that. You have to create a new server and try to migrate the roles / applications to it. This posting is provided "AS IS" with no warranties or guarantees , and confers no rights. Microsoft Student Partner 2010 / 2011 Microsoft Certified Professional Microsoft Certified Systems Administrator: Security Microsoft Certified Systems Engineer: Security Microsoft Certified Technology Specialist: Windows Server 2008 Active Directory, Configuration Microsoft Certified Technology Specialist: Windows Server 2008 Network Infrastructure, Configuration Microsoft Certified Technology Specialist: Windows Server 2008 Applications Infrastructure, Configuration Microsoft Certified Technology Specialist: Windows 7, Configuring Microsoft Certified Technology Specialist: Designing and Providing Volume Licensing Solutions to Large Organizations Microsoft Certified IT Professional: Enterprise Administrator Microsoft Certified IT Professional: Server Administrator Microsoft Certified Trainer

Hi, Thanks for your post. For detailed steps of upgrading Windows 2000 to Windows 2008 R2, you may refer to the following article. It also included references of various tools and useful resources. Hope it helps. Upgrading from Windows 2000 to Windows Server 2008 R2 http://download.microsoft.com/download/5/B/D/5BD5C253-4259-428B-A3E4-1F9C3D803074/Upgrade_from_Windows_2000_Server_to_Windows_Server_2008_R2.docx Best Regards, Aiden TechNet Subscriber Support If you are TechNet Subscription user and have any feedback on our support quality, please send your feedback here.Aiden Cao TechNet Community Support

Hi, Thanks for your post. For detailed steps of upgrading Windows 2000 to Windows 2008 R2, you may refer to the following article. It also included references of various tools and useful resources. Hope it helps. Upgrading from Windows 2000 to Windows Server 2008 R2 http://download.microsoft.com/download/5/B/D/5BD5C253-4259-428B-A3E4-1F9C3D803074/Upgrade_from_Windows_2000_Server_to_Windows_Server_2008_R2.docx Best Regards, Aiden TechNet Subscriber Support If you are TechNet Subscription user and have any feedback on our support quality, please send your feedback here.Aiden Cao TechNet Community Support

Hi, How are things going? I just want to check if the information provided was helpful. If there is any update or concern, please feel free to let us know. Best Regards, Aiden TechNet Subscriber Support If you are TechNet Subscription user and have any feedback on our support quality, please send your feedback here.Aiden Cao TechNet Community Support