Upgrading Internet Information Server

Hi,

  I have an old standalone server box (32bit architechure) running WIndows Server 2003 Std. with 4MB RAM and I run multiple websites including Adobe Coldfusion version 7 in IIS6.  I like to move that server to VMWare host ESXi V6 (newest & greatest CPU, RAM, hard drives , Coldfusion  version 11).
  I know I can use VMware vCenter Converter Standalone to move this Win2003 Server to VMWare host as Virtual Machine and so that I can run it on the new VMWare host and I don't have to do anything. That is not a problem.
  However since these websites will be running off a new hardware, I like to upgrade current W2003 OS to either Windows 2008 32bit/64bit,  Windows 2008 R2 64bit, Windows 2012 64bit or WIndows 2012 R2.

  With that I have a few questions:
   (1) Are there benefits in upgrading W2003 to W2008 or W2012?
   (2) If I upgrade, how can I get W2003 upgraded to W2012 R2 (if W2012R2 is what is recommended)?
  (3) Should I upgrade W2003 to W2008 on current box first and move it to VMWare host or move W2003 to VMWare first and perform an upgrade?
  (4) Can you upgrade W2003 32bit OS to W2008 R2 64bit OS?
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sgleeAsked:
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arnoldCommented:
To maintain flexibility if having one operational while you fix whatever might be going on with code/functional issues with the new IIs version/OS
I would recommend you install a VM with the Os you want with IIs version configure it install the newer version if cold fusion that will run on that system and them setup the site as a test on it, ...........

Once the test site is functional and has no issues, make the adjustment to point the external access to the new VM.

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sgleeAuthor Commented:
@arnold
Installing newest OS in new VM (preferably Win2012 R2 & CF version 11) on new VMWare host would be my preference. The only thing is that there are quite a number of web sites to re-create, transfer of data, and figuring out whatever programs that might have been installed  for existing websites is a daunting task.
David Johnson, CD, MVPOwnerCommented:
 (1) Are there benefits in upgrading W2003 to W2008 or W2012? Those O/S's are supported S2K3 is no longer supported as of July 14th
  (2) If I upgrade, how can I get W2003 upgraded to W2012 R2 (if W2012R2 is what is recommended)?
Migrate only no direct upgrade path

  (3) Should I upgrade W2003 to W2008 on current box first and move it to VMWare host or move W2003 to VMWare first and perform an upgrade?

Do it all on the virtual machine. This way you can do an a/b comparison having an original frame of reference.

  (4) Can you upgrade W2003 32bit OS to W2008 R2 64bit OS? you cannot upgrade ANY 32 bit ]OS to a 64Bit OS
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arnoldCommented:
Upgrade path even on a cloned VM of the current one is full of risk.
Taking your time and refamiliarize yourself with the sites and their dependencies along with documenting it might be the needed opportunity.
There are significant configuration/setting changes among the newer versions IIS 7,7.5, and 8 that might be inevitable in terms of requiring an update to the coldfusion version which might or might not run on the newer setup, or would be so limiting as to defeating the hardware enhancements you made.
With two VMs. You could transition a site at a time.
sgleeAuthor Commented:
OK. It sounds like
(1) I better set up IIS 8 or 8.5  on the new VMWare host and migrate one website at a time. It is going to be FUN!

Has anyone moved standalone W2003 running IIS 6 into VMWare host as VM (using VMware vCenter Converter Standalon) and run into any issues?
If I can do that, at least, I can get rid of old hardware.
arnoldCommented:
Initially, nat the network of the VM within VMware to make sure you can run both at the same time.
Are you USIng host headers or does each site without a need for SSL has its own LAN.
Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Has anyone moved standalone W2003 running IIS 6 into VMWare host as VM (using VMware vCenter Converter Standalon) and run into any issues?

No issues, other than the standard methods required to complete a P2V. e.g. selecting the correct version of Converter, that support 2003.
sgleeAuthor Commented:
I am using host headers.
Once I move standalone W2003 running IIS 6 into VMWare host as VM (using VMware vCenter Converter Standalone), I am going to turn off physical server and turn on the VM.
Then I will have time to test the functionality of existing websites. If there is an issue that I can not resolve, I can always go back to physical machine.
arnoldCommented:
You could use the sink or swim method, or use the natted VMware VM and test each site's functionality before transitioning.
Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
Check all IP Addresses are correct on the VM, these interfaces will all need to be re-entered on the new VM

Just be cautious if you go back to the physical machine, the Domain SID may be broken, e.g. trust relationship with domain will have failed, so you will have to re-add to domain.
sgleeAuthor Commented:
"these interfaces will all need to be re-entered on the new VM" ---> so you are saying that the static IP address information will NOT be automatically carried over to the VM?
" trust relationship with domain will have failed, so you will have to re-add to domain" --> That is good to know. I will make sure, if I ever have to go back to original physical W2003 machine, I will disjoin and rejoin it to the domain.
Andrew Hancock (VMware vExpert / EE MVE^2)VMware and Virtualization ConsultantCommented:
That is correct, have you never used VMware Converter or performed a P2V ?

It performs a conversion, so physical hardware is swapped for virtual hardware, e.g. the network interface is changed, so you will have to re-enter ALL the TCP/IP information.
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