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Test Environment setup for upgrading Exchange 2003 to Exchange 2013

Looking for a bit of input for the best course of action.

As of right now:
Windows 2003 Server - DC
Windows 2003 Server - Exchange

First: Is it best from exchange 2003 -> 2007 -> 2013? or should i go from 2003 -> 2010 -> 2013?

Second: I also plan to upgrade my DC to Windows 2012. Should i do this before or after exchange migration?

With all these changes, I really want to do a test run beforehand. After 4pm, no one is on location.

I have 3 new servers running Windows 2012.

1 server is running Standard version of windows 2012 with AppAssure 5, so i have a base image of the DC and Exchange Server.

1 Server is running Datacenter version of Windows 2012. (would eventually be my DC)
1 server is running DataCenter version of Windows 2012. (would eventually be my exchange server)

I installed Hyper-V on DataCenter versions of Windows 2012.

Since no one will be onsite, is it best to just shutdown the current production servers then load up VMs of my current DC and Exchange and test out the process? This seems it would give me a true 1:1 working environment. Or should i load the DC/Exchange VMs on a different subnet and not have to shutdown the production servers at all. My only concern here is, they won't be able to access the internet and i currently don't have any VLANs setup on my switches.

Lastly,: Am i thinking too much into this and should just go straight into the upgrade process? i'm just afraid of what bumps i might run into. I want to make this upgrade as smooth as possible with minimal downtime during work hours.  

1 Solution
AmitIT ArchitectCommented:
Your approach in testing upgrade in test environment is correct. This will help you during the actual migration. Make sure to document all steps. Now for other question, here are my suggestion.

1) Choose upgrade path from 2003>2010>2013 Why? 2010 much easier to install and play.
2) DC Migration you do later or run as separate project altogether.
3) Don't need to shutdown or disturb production servers. Clone them and use an isolated subnet for testing. You don't internet, download necessary binaries before starting the process.
4) You are thinking too much? That is a right approach, do as much possible brain storming

Apart from above use Exchange 2013 deployment assistant tool, that will help you to provide all necessary steps for migration. Not sure how big is your environment is currently, so don't be in rush for the upgrade plan in production.

You also need to keep separate migration plan for your production application, fax, printers or custom scripts etc. As in 2003, authentication was not that big issue, however in 2010 or 2013 it is a big deal and application might fail to send emails via Exchange 2010 or 2013 servers.

Next is Cert, that is very important part. Plan your cert requirement well before planning to purchase, what all SAN names you need in your cert.

Also note, you need to upgrade you client also at same time, Outlook 2003 is not supported with 2013, so you need to run desktop upgrade project along with your exchange migration project in actual production environment.

Hope this helps....
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