Plan for a Migration to Windows Server 2008 R2

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This article will be the second part of 4-part series articles on deployment of Windows Server 2008 R2. This
4-part series articles will talk about the options available to move to Windows Server 2008 R2, and what planning and
considerations are required for a successful migration.

With the introduction of Windows Server 2008 R2, x86 (32-bit) architecture hardware is no longer supported. Due to
this change, for the major server hardware out there, a migration process would be required. A typical migration
process involves the following steps:

  1. clean installation of the operating system
  2. installation of server role(s)
  3. move data and settings from source to destination (new) server
  4. point the clients to the new server

Migration steps are different based on the server role or the applications to be migrated. There is no single step
to migrate all types of server roles or applications, hence there are quite a lot of factors we will need to
consider, which will be covered below.

Windows Server 2008 R2 Migration Tools

Microsoft has tons of tools available to ensure a smooth migration. These tools will help speed up the deployment
of Windows Server 2008 R2 in your existing infrastructure, by ensuring that your network infrastructure and existing
hardware are supported and by providing recommendations on a successful migration.

Generally there are two stages involved for the migration: Planning and implementing.

For planning, the Microsoft Assessment and Planning (MAP) Toolkit 4.0 provides an inventory, assessment and reporting toolkit to assess IT infrastructure in an organization without the need of a software agent.

There are two tools for implementation:

The Microsoft Deployment Toolkit (MDT) 2010 allows the deployment of Windows 7 and Windows Server 2008 R2 through a common console. MDT also allows an automated process to deploy server and desktop operating systems.

The Windows Server Migration Tool is a feature in Windows Server 2008 R2 that allows the migration of some server roles, features, operating systems, shares and other data from a supported Windows Server operating system.

Performing a Migration

Here’s a basic outline of the migration process:

Step 1: Planning

MAP 4.0 is able to scan and assess the computers/servers to ensure that it is possible to migrate to Windows 7 or
Windows 2008 R2. The big advantage of MAP 4.0 is that it does not require any software agent to be present in the
computers/servers to be scanned for it to work. MAP 4.0 takes advantage of Active Directory, Windows Management
Instrumental (WMI) and Remote Registry to work.

Once MAP 4.0 has finished assessing the network environment, it will produce reports in Excel and Word. The
assessment reports will show the total servers in the environment along with their operating system version,
applications installed, IP configuration, and the next steps for a migration.

Through MAP 4.0, the server roles that need to be migrated can be identified.

Step 2: Implementation/Migration

Once the infrastructure has been assessed, it is time to deploy. Deployment can be done by using Microsoft
Deployment Toolkit (MDT) 2010, and Windows Server Migration Tool, as part of Window Server 2008 R2.

There are two general scenarios which are possible:

Scenario 1: Migration From Windows Server X86 to Windows Server 2008 R2

As an in-place upgrade is not possible for cross architecture operating system, a migration of settings and data
will need to be done. This involves using both MDT 2010 and Windows Server Migration Tool, which is a feature as part
of Windows Server 2008 R2. However for Windows Server Migration Tool to work, you’ll need to meet the following requirements:

  • source server is running on x86 or x64 hardware
  • migration from physical OS to virtual OS, or vice versa.
  • source server is running Windows Server 2003 SP2, 2008, 2008 R2 or 2008 R2 Server Core

If the source server is not running any of the above listed operating systems, the source server will need to be
upgraded to any of the above server operating system before a migration to Windows Server 2008 R2 can be done.

To migrate server roles to Windows Server 2008 R2, here are the steps:

  1. Using MDT 2010, deploy Windows Server 2008 R2 on a bare machine. It is also possible to deploy by using Windows Server 2008 R2 DVD, but it would be recommended
    to use MDT 2010 for flexibility.
  2. From Windows Server 2008 R2, install the Windows Server Migration Tool feature.
  3. Create a shared folder, and use the tool smigdeploy.exe (under %Windir%System32ServerMigrationTools) to create the deployment files and save them in the shared folder.
  4. Refer to the links to the whitepaper at the bottom of the article (table 2) on migrating respective server roles.

Scenario 2: Migration From Windows Server X64 to Windows Server 2008 R2

Although an in-place upgrade can be done from Windows Server 2003 or 2008 x64 to Windows Server 2008 R2, but
depending on the network environment, this could end up very messy. It would be better to migrate to a new hardware
or a virtualized environment if the IT environment is complex.

If an in-place upgrade is preferred, the general steps are:

  1. Duplicate the source server onto a testing environment.
  2. Do an in-place upgrade on the testing server.
  3. Test and troubleshoot the testing server if problem arises.
  4. Do an in-place upgrade on the production server.

Migration Whitepapers

The migration process is different, depending on several factors, including:

  • server roles
  • domain controller
  • custom applications
  • services uptime
  • complexity of the role (clustered or geographically disbursed)

The migration process is not straightforward, so it is very important to read up on the migration guide for
each and every server role, and test it out in a testing environment before migrating a production server.

Since we will not be covering on how to do a migration for all roles and applications, the following lists will point you to the right place for the migration whitepaper.

Migrating Server Roles:

Migrating Settings/Configurations:

What’s Next?

Migrating to a new server is always a challenge; however Microsoft has tools ready to assist in a smooth
migration. As long as migration testing is done and migration steps are followed carefully off the whitepaper, it
should be quite a straightforward process. There are other solution accelerators
available from Microsoft, but this article only covers those needed for a successful migration to Windows Server 2008

In the next article in this series, we’ll look into application compatibility, and how do we overcome those issues.

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