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drewmun

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Would this work?

I need to upgrade a server from SBS 2008 to SBS 2011 and am contemplating the various ways to make the transition seamless. One thought I had that I would like to try out is to make a virtual image with VMware (or something else) with SBS 2011 on a spare server I have then configure the computers and network with it. This way I can ensure that everything is working on this image without issue. Then, satisfied, I'd wipe the current SBS 2008 server and load that same vm from the spare server into the production server. Would that work?

The other thought is to try an upgrade, but I've never done a server OS upgrade on the same machine.

This company has a few programs that run off the server and I basically want to ensure that they work on the new vm before messing with the current server.
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Andrew Hancock (VMware vExpert PRO / EE Fellow/British Beekeeper)
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Yes, that is possible, you can create a Virtual Server with SBS 2011 on VMware, and then transfer the virtual server to a physical server called a V2P using Acronis Uniersal Restore

http://www.acronis.com/backup-recovery/smallbusiness.html#add-ons-universal-restore
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drewmun

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Not quite what I meant, but thank you. I'm also not looking to spend any money on software for this, simply trying to be efficient with my time.

I meant that after I had created the working vm on the spare server and configured every computer to work with it I would then wipe the original server, put vmware on it, then transfer the image over and call it a day (after testing of course)
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Lee W, MVP
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Good answer, but I don't want to do a migration, I'd rather do a clean install. I've already transferred everyone's email into Office 365 now the server will pretty much function simply as a file server.

I originally intended to simply do a clean install then load their data back on it as I connect everyone back into the server. (Would changing the domain name be important?). This company only has about 10 employees so it won't be much of a hassle. They do have one program, Instar, which runs off the server. Really the only reason I wanted to set up a VM on a spare server was to ensure that program was still working.

The current SBS 08 install is full of problems and I'd rather create a fresh domain. I appreciate your feedback.
you can do it for free, VMware ESXi is free.

Windows Backup is Free, complete a Restore to your physical server, and run a Repair.
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When would I run a restore? After the upgrade? Appreciete the response hanccocka but I'm not sure I understand what you meant.
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Again thanks for the amazing response.

I ran a migration in this office from SBS 03 to SBS 08 and it was an absolute nightmare, pretty much why I'm doing things this way. The server has about 15GB of email archived in public folders which I've converted into a shared mailbox in 365. When I ran the migration before it constantly timed out when it attempted to transfer those files. I think the estimate it gave me was something in the order of three weeks to complete the transfer. At that time I ended up exporting the public folders into a pst, ran a fresh install of SBS 08 then loaded the public folders in outlook. I suppose I could simply delete those things before the transfer.

When talking about migration, I need a second server correct? I cannot simply do an upgrade of the existing box?

Yes, I'm going to run essentials. Is it really an upgrade to use essentials 12? its about $100 more expensive and looking at features I haven't been able to discern much difference between the two,
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I've looked at samba and freenas actually. I'd prefer something that would be easier to manage for the employees so they don't need to call me up all the time.
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Ok, everyone might be convincing me to do a migration instead. I simply can't upgrade right? I need to pull everything into another server that has Essentials on it, then either transfer it back or copy the vm back over? (edit- I see that was answered while I typed this)

What technical issues would I run into by rebuilding the domain? I've done it before and didn't run into issues, but it really was a different domain even with a different name. Would building a new domain and keeping the existing domain name cause issues? Not sure what else I'd run into, I understand people might have a few small issues with favorites and stuff.
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Ok, let's say I do a migration (And thanks for everyone's responses so far! )

Exchange and sharepoint won't transfer or cause any issues right? Like I said, everyone's email is in Office 365 currently  (whew) so it should be a pretty easy transfer correct? I understand the new versions of Server are made with Office 365 in mind, so connecting the two should work well right?

Even with a migration I'll need to change many people's settings anyway. There ended up being too many administrator accounts so I will need to demote everyone but one.

It should be pretty easy on paper. Install Essentials on another server with esxi, demote current one and migrate, then move the image from the new temporary server to the new one. Everything sound correct?
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