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Is it possible to upgrade Windows 2003 to Windows 2008 from a mounted ISO (e.g. with Daemon Tools)? It would have to copy all needed files from the mounted ISO and install from there... I don't think the install/upgrade process supports this... I'm looking for any kind of confirmation about this.

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@GregD: take a look at my questions. Many of them don't have satisfactory answers that I could accept. – Mauricio Scheffer Dec 29 '10 at 17:27
Have you considered offering a bounty? – GregD Dec 29 '10 at 17:28
@GregD, a bounty doesn't always help. I've offered thousands of points in bounty on various questions and still not had a decent answer. Besides, mausch doesn't have enough rep to be able to offer much of a bounty anyway. – John Gardeniers Dec 29 '10 at 20:57
up vote 5 down vote accepted

First of all, upgrading from 2003 to 2008 is bad news. Microsoft supports it, but does not recommend it. If you can do a clean install, that's going to be your best bet.

Secondly, what you want to do is not possible. You'll have to find another way to boot up to the CD as you cannot start the install from a mounted ISO. If you don't have a drive you can use, you can look into delivering the image from WDS on another server.

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Thanks. I'll just get an external drive. Server is kinda old, only has a CD drive. – Mauricio Scheffer Dec 29 '10 at 20:32

Extract the ISO to a flash drive and perform the upgrade that way instead of using software tool. Main issue to watch for is that the drive letter does not change after reboot process. But as stated above in place server upgrades can lead to a bad few days.

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As Jason said, it's not a good idea to upgrade.

If your server is a HP Proliant, you can mount the .iso image in iLO (via the virtual disk) and move on with life. (I assume that Dell and IBM's out-of-band tools have similar capabilities...)

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if it's a proliant, you can also use the HP SmartStart setup and install directly from the ISO sitting on a USB drive.. – Rex Dec 29 '10 at 20:54
Thanks. It's a Dell PowerEdge, I'm not at the office right now so I can't tell the exact model, but it's quite old, I don't think it has these capabilities. Easier to plug in an external DVD drive :) – Mauricio Scheffer Dec 29 '10 at 21:46

I have used a similar process for machines which Windows 2008 doesn't officially support, but not exactly as an upgrade.

I've installed Windows 2000 because IBM supported it out-of-the-box and offered installation tools (ServerGuide). Bare install, no patching or updates because it's temporary.

Then I've copied the i386 folder from the install ISO to a folder on the 2000 installation. From there run the command-line install (it used to be winnt /o /x or something like that) and install 2008 to a new directory.

You'll then end up with a dual-boot 2000/2008 server. A few hacks with the boot loader (It used to be simple to edit boot.ini but now you have to work in the boot loader database with cryptic commands.) will let you delete the 2000 boot and change the default loader to 2008. After that you can delete the 2000 folder.

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