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Yesterday I spent far too much time downloading and installing software on Windows Server 2008. I only had to install a simple server for SQL Server 2008 Express using Microsoft's Web Platform Installer, then configure it to enable remote connections. Everything had to be attended, wasting my time. On a Linux system, this would be trivial to automate, but this is Windows.

I do this very rarely, but in the future I would like to make this take as little time as possible. I could do a disc image with everything I installed and configured, but is there a better way? I know nothing of advanced deployment techniques on Windows. Ideally I would like to be able to remotely re-install the OS, or have an unattended install (which I know is possible). Any tips to make the software I need easier to and install and configure with minimal interaction necessary would be helpful. I don't expect everything I asked for to be possible and easy to do. Basically, If any part of it can be done quicker or at least without user input, that's what I'm looking for.

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Interestingly enough, the ServerFault Blog touched on this very topic recently:

What you're asking for can be done. However, in my experience the effort expended to set up the environment to do so is pretty large. When expressed in units of "effort to hand-install a server", the effort break-even point is further down the road than it is for Unix. If you're only doing it once or twice a year and have no prospects of having to do it a lot in a short period of time, it's still easier to do chunks of it by hand.

It IS possible to PXE boot a naked server, install Windows based on a prepared answer-file, deploy the SQL software to it, and configure the SQL software. And if you really wanted to go there, Wake On LAN capability would allow you to trigger this all from remote after a server gets plugged into the network. I do recommend the blog-post for a list of the technologies used in each step.

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A remote install of the OS isn't too important, but it would have saved me two trips to our datacenter yesterday. I'm mostly interested in doing all of this faster. – Chris Jun 24 '11 at 15:53
@Chris - "Faster", or without as much human attention when changing tasks? Because the only way to do it "faster" is with imaging or VM templates. Using automation doesn't make it faster, but it makes it more standardized and requiring less hands-on, which might be what you mean by "Faster." – mfinni Jun 24 '11 at 16:19
I clarified my original question. I mean less attention needed; I want to be doing something else while windows is installing to the point where I'm not checking it constantly to see if there are any prompts. Newer versions of windows require far less attention than older versions. The Web Platform Installer is a pretty lame attempt at making things easier. I was installing SQL Server with it yesterday - three reboots that I had to watch for while installing it and the requisite software, and one prompt for a password for the SA account. – Chris Jun 24 '11 at 16:21

If you used a virtualised system such as Hyper-V or VMWare ESXi you could create templates/clones of the various stages or configurations of installations to either re-use directly or branch from. This can be an astonishingly fast way of deploying customised servers.

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I had tried this over a year ago and had odd problems using ESXi. Basically, I would boot a few times and then my image would no longer boot. VMWare support told me it was because I was using a SATA drive and not something more complicated, which I found bizarre. While I had some success and wanted to continue trying to get it working, my boss said to stop perusing the idea so I did. – Chris Jun 24 '11 at 15:54
I see, that's because ESXi is really a datacenter-level product and as such they insist on using DC-quality kit such as SAS drives etc. – Chopper3 Jun 24 '11 at 16:06

Ghost is one option

As I see it using something like Ghost can be pretty (extremely) helpful for this sort of thing - however not as much if you're dealing with differing hardware configs.

Make your own installer

The utility nLite (or RTSe7enLite for Win7) is really really awesome for helping you create your own custom Windows installation disks - with that you can arrange for software updates to be preinstalled as well as various software packages too. This is more work to set up than Ghost, but is free to use and will deal with differing hardware too.

I prefer VMs myself

Personally, I totally roll with VMs and I prefer VMware ESXi. I've not had the problem you did. A similar alternative (that I haven't tried in a year) to VMware ESX is Citrix XenServer. Last time I explored Citrix XenServer, I found the support utilities to be too underpolished for my use, but I continue to hear good things about it. VMware also has the Virtual Appliance Market Place, which I think is very handy.

I love the portablity of VMs, the scalabilty of their hardware footprint and the abilities to snapshot and make copies, I find those features invaluable and extremely enabling.

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