How to Migrate from Server 2008 to Server 2019 / 2016, and keep applications, profiles, shares and data

Server 2008 End of Life is January 2020. If you’ve been postponing your 2008 migrations, now is the time to get those over with. Luckily, this can be much easier than what you’d expect: in this article, we’ll describe how to perform a migration from Server 2008 / Server 2008 R2 to a new Server 2019, 2016, or 2012 – including migration of server applications, databases, user profiles, shares and data. We will also cover role migration best practices and tutorials.

Migration covered here is native migration – not app virtualization. You can use these methods to migrate from physical to physical, physical to virtual / Cloud, Cloud to Cloud etc. Virtualization can be added for compatibility workarounds, but will not be covered in this tutorial.

The goal of this tutorial is to allow to complete a server migration in less than 4 hours of actual work time for application and file servers (not counting “unattended wait” times for data transfer), and less than 24 hours for role-focused servers (although complicated cases may require more time).

The software used to achieve that is Zinstall WinServ.

Just want to find out how to automate the migration, and don’t need a general tutorial?
Click here to skip to the part with the actual migration process.
Or, if you need to migrate workstations, click here for migration to Windows 10.

WinServ Server Migrations are also available from IBM Services, as part of their full service package for large scale deployments. Contact your IBM account team in your region for more information.

Video demo – automatic server migration tool

Before you begin: Audit your servers and plan your migration.

Audit your servers: In a typical environment, you’ll have quite a few different server types. Typical groups would include domain administration servers (DC, DNS, DHCP etc.), web servers, DB servers, application servers, files servers and so on.

This tutorial focuses on the typically more numerous group – application servers, database servers, file servers (mainly because these migrations can be readily automated, unlike role migrations).

Schedule your migration time slot: Migrations take time, and during that time, your users may be affected to some extent. If possible, try and schedule the actual migration to be performed after hours or during a weekend. Note that you don’t actually have to stay there yourself at that time: application migration can be performed remotely or launched in advance in unattended mode.

Verify your backups are up to date, and are actually restorable: Any major upgrade may go wrong, and without a valid up-to-date backup, you risk losing everything you’ve had on the server. Make sure to verify that the backup you have is not damaged and ready to be restored if needed!

Decide on replacement type: Once you have decided to replace a server, you have several options regarding what the replacement will be. It may be a physical Windows 2019 server, a virtual server running on premise, or a Cloud-based server running off premise (such as migration to Azure or migration to Amazon AWS). If you are using Zinstall WinServ, it supports any of those transfers, so migration difficulty does not vary significantly with your choice.

In-depth demo: Windows Server application migration

How to migrate from Server 2008 to Server 2019

The process below outlines the migration steps for moving from Server 2008 to a new Windows Server 2019 / 2016.

Option 1: Direct migration from Server 2008 to 2009 over the network

1. Before you begin, consider disabling the firewall on the old server, or at least adding Zinstall to its whitelist, so that the firewall does not interfere with the migration.
2. Run Zinstall WinServ on both servers.
   Note: You can get Zinstall WinServ here, and its user guide here.
3. Select the first option, “Moving between two machines”, on both servers.
4. If you do NOT want to transfer server applications, and are only interested in a profile, data and shares transfer, switch the radio button on the main screen to “profile and settings only” mode.
5. On the source server, choose the “Source computer” option, and leave it running. It will be waiting for connection from the new one.
6. On the new Server 2019 / 2016, choose the “Target computer” option.
7. WinServ will automatically detect the source server. Alternatively, if the servers are on different networks, you can manually specify the source server’s IP address.
8. If you’d like to select exactly what you want to transfer, press the Advanced menu. If you just want to transfer everything, you don’t need to go to the Advanced menu.
9. Click Next and then Go to start the migration.
10. The transfer will take a while (depending on how much data you have to transfer), and report to you when done.
11. That’s it!

Option 2: Indirect migration from 2008 to 2019 / 2016, via intermediate storage

1. Run Zinstall WinServ on both servers.
   Note: You can get Zinstall WinServ here, and its user guide here.
2. On the source server, select the 3rd option, “Moving from Machine to Container”
3. Choose the container location (such as a network share, a NAS, a USB hard drive – any type of storage), and press Go to perform a full capture of the source server to that location.
4. On the new 2019 / 2016 server, select the 4th option, “Moving from Container to Machine”
5. If you do NOT want to transfer programs, and are only interested in a profile, data and shares transfer, switch the radio button on the main screen to “profile and settings only” mode.
6. Specify the location of the container created in step 3.
7. If you’d like to select exactly what you want to transfer, press the Advanced menu. If you just want to transfer everything, you don’t need to go to the Advanced menu.
8. Click Next and then Go to start the migration.
9. The transfer will take a while (depending on how much data you have to transfer), and report to you when done.
10. That’s it!

Server Roles migration

This part of the migration is done manually, and multiple tutorials exist that may help. We recommend John Savill’s excellent guide: Winding Down Windows Server 2003 in Your Organization. Information below is based on the article above.

1. IIS migration: If all you have running on IIS 6 are basic HTML pages or Active Server Pages (ASP), you can copy the content to the IIS version running on Server 2012 or Server 2012 R2, then update the DNS records to point to the new IIS server. However, organizations typically have more complex configurations. The good news is that you can use a migration toolkit named Web Deploy 3.6. If you need to migrate websites to Microsoft Azure Web apps, see Azure Web App Migration Assistant.
2. DC and AD migration: Providing you have followed best practices, your domain controllers (DCs) don’t run any other software, which means the existing domain and forest will be prepared for Server 2012 or Server 2012 R2. In this case, you need to create new DCs running Server 2012 or Server 2012 R2, migrate the Flexible Single-Master Operation (FSMO) roles, migrate any certificates or other items, then decommission the Server 2003 DCs. To introduce Server 2012 DCs, the forest (and therefore the domains) must be Windows Server 2003 mode. For detailed guidance on migrating DCs, see Upgrade Domain Controllers to Windows Server 2012 R2 and Windows Server 2012.
3. DHCP migration: DHCP scopes provide the IP addresses given to clients, along with their IP configuration (e.g., gateway, DNS server). To migrate DHCP scopes, the best option is to export the scopes from the Server 2003 instance, then import them to the Server 2012 or Server 2012 R2 instance. Full details on this approach are available in the TechNet Networking Blog post “Steps to move a DHCP database from a Windows Server 2003 or 2008 to another Windows Server 2008 machine.” If there is any delay in the DHCP scope export and import and a risk of IP address reuse, you can configure the DHCP server to check if an IP address is being used before it’s allocated by enabling address conflict detection.
4. DNS migration: If you’re hosting DNS on Windows, you’re likely integrating it with AD and your DNS servers are DCs. Therefore, when you migrate AD, the DNS configuration will move as well. It’s important to remember to migrate any DNS server configurations, such as forwarding. If the DNS servers will be hosted on new IP addresses, you need to make sure that you update any static IP configurations and all DHCP configurations. To avoid this time-consuming task, most organizations will change the IP addresses of the new servers to that of the old servers once the old servers are retired.
5. Print services: Like file services, printer configurations and shares must be migrated from the source server to the target server. In addition, you’ll need new printer drivers that are 64-bit and compatible with Server 2012 or Server 2012 R2 as well as with modern clients. Microsoft has a print migration wizard and command-line tool you can use for migrating printer services. You can download these tools from the Migrate Print and Document Services to Windows Server 2012 web page.
6. Exchange migration: Upgrade from Exchange 2007 to Exchange 2013
7. SQL server migration: See Supported Version and Edition Upgrades

Dealing with incompatible applications:

Some legacy 3rd party applications running on Windows Server 2008 may be incompatible with Windows Server 2019 (or 2016). For example, if you are running SQL 2005 on Server 2008, it won’t run on anything newer – no matter whether you migrate it manually or automatically. It is strongly recommended to eliminate these applications from the production environment as soon as possible.

If these applications cannot be eliminated immediately, and are mission-critical for continued operation of the organization, the recommended option to preserve them operational is to perform a virtualized migration of those applications, into a virtual Server 2008 instance running on newer replacement server. Then, continue to take the steps required to phase those applications out and stop running the virtualized 2008 instances.

WinServ is application-generic, and can migrate even custom and in-house applications that have not been seen by the outside world – as long as they are capable of running on the new server. Here is a partial list of common applications that our customers have migrated in the past:

• MS SQL
• MySQL
• SAP (including SAP Business One)
• Oracle
• Sybase
• DB2
• Java Application Server
• Crystal Reports
• Avaya
• PeopleSoft
• JD Edwards Enterprise One (JDE E1)
• Citrix
• Apache (Windows only)
• WebSphere
• Microsoft Dynamics

After the migration:

Once the migration process is complete, it is time to verify the results.

1. You may need to adjust your domain’s DNS to point to the new server where needed. For example, changing the CRM-SERVER DNS entry to the new server’s address.
2. Same goes for login scripts and GPO policy.
3. Launch every application and console you use, and verify they load correctly.
4. Using a client workstation, verify that clients can access the migrated server correctly and their applications run without issues.

Congratulations! Your server migration is now complete.

Ready to migrate your 2008 servers?

Get Zinstall WinServ here

You can also contact us for assistance, volume licensing, and help in setting up a POC.