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I am new to server administration. I need to upgrade the windows server 2008 R2 to 2012 R2. Since windows server 2008 is a production server, I am afraid to do the in-place upgrade.

Basically I need the new server (server 2012 R2) to be the identical to the current server (server 2008 R2). And once the new server is up and running, I can take down the current server. How can I achieve that? Which of the following options is best for the solution.

  1. Create an entirely new server and copy everything such as local users, groups, IIS config, disk permission information from 2008 R2 to 2012 R2. (using Windows server backup)

  2. Create a replica of the current server and perform in-place upgrade on that server. (Using backup image of the first server) (Obviously, I would want the new server to have a different name and SID so they can both be active in the same network and joined to my domain.)

Which is the right way to approach the task?

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    This is a very broad question and can hardly be answered here. Every product (IIS, Fileserver, etc.) needs an individual strategy. Do you also install a new Active Direcotry? When not, the users shouldn't have changed. – marsh-wiggle Dec 3 '18 at 15:48
  • @marsh-wiggle Thanks for your reply. I reformatted the question. Please check it now. thanks. – user3020466 Dec 4 '18 at 11:01
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    I would install a new server and migrate the data. For the filecopy we use Beyond Compare scootersoftware.com, which has a 30 day trial period. With the on board comman line tool "net users" you can export the names of the present users and make a little script to create them in the new environment. For the IIS migration you can take one of the step by step tutorial on the internet. – marsh-wiggle Dec 4 '18 at 12:18
  • @marsh-wiggle Thanks a lot for your reply. But the net users command does not copy the passwords along with usernames.right? I need the settings to be unchanged from the current server. Additionally, if the question is more clear now, can you change the status of the query back to normal from put on hold? – user3020466 Dec 4 '18 at 15:04
  • Microsoft has always recommended installing a new server and migrating your services and applications. – Michael Hampton Dec 4 '18 at 15:48
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It depends on how much downtime is tolerated, or if this is a Virtual Machine.
If you can take a VM snapshot, you will be able rollback immediately.
The in-place upgrade doesn't usually take longer than 3 hours, but I am assuming your HDD is less than 1 TB.
In my experience in place upgrades work smoothly 95%, with the most common problem there being network adapters getting reset so just write down your adapter's IP and DNS info. One time the web.config file was lost in IIS but was quickly recovered from a file-system backup.
If this is a large server, I would create a new 2008 server with a new IP and host-name do a complete Windows Server Backup to that server.
https://www.experts-exchange.com/articles/30742/A-Guide-to-Volume-Shadow-Copy.html
In place migrate from 2008 -> 2012 on the new one, make sure it works before switching names to the new one. My reasoning behind doing this instead of manually moving files to new 2012 R2 server, is that this way the in place migration ensures that the software is compatible with 2012 R2.

  • it is a large server with multiple web servers and a sql server running. So does the option 2 mentioned in my question work for this situation? ( creating a backup image and do the in-place upgrade) – user3020466 Dec 5 '18 at 8:13

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