Enterprise Agenda: The Great Migration of 2016

Posted on August 29, 2016 by Brad Sams in Windows Server 2016 with 0 Comments

Enterprise Network Hero

Later this year, Microsoft will release Windows Server 2016 and with it comes a plethora of new features that will make it easier to administer your network, improve security and make life as an IT pro a little bit easier. If you plan to upgrade, you can never start preparing too soon.

In this edition of the Enterprise Agenda, I will cover the high points of creating a battle plan for a migration to Windows Server 2016 that should help you avoid the obvious issues and have the smoothest upgrade experience possible.

Step one — plan: You can never over plan this type of a migration, which means breaking out your favorite to-do list application. You should create a simple list in Word/Excel or dive deep with Microsoft Project. Whatever your tool of choice, it’s important to buffer in extra time for unexpected issues and it’s OK if you end up not needing it; when was the last time management was upset that you were ahead of schedule?

Step two — define what goes into the plan: This consists of several steps starting with research, preparation, communication, practice, backing up, execution and post upgrade documentation. All of these steps are critical to a successful upgrade and skipping one or any will result in a shortcut that expands the probability of a failed upgrade or extended outage.

Step three — research how, when and what you will upgrade: Take inventory of which servers you will migrate and determine the order to do them in so you understand what challenges you will face with each migration. Once you know which servers to move and when, it’s critical to look into all the applications that those servers support.

By researching to see if Windows Server 2016 already supports your applications, this will give you guidance on any issues that may arise. I know that many of the readers of Petri use Veeam software. Veeam recently announced that they are ready for Windows Server 2016, as have many other large vendors.

The research step should be thoroughly completed before moving on to any other step as it will help you to identify pain points before they arise and can help you schedule later steps around trouble spots. Once you fully exhaust this stage, it’s time to inform business leaders on the upgrade path.

Step four —communication to reduce the impact of the migration: While it may be possible to do a seamless transition in some instances, not every organization has this capability; this is why your research and planning phases are critical.

When you notify business leaders of the impact to their business operation, you should tell them exactly when the service will go offline and when they should expect the operation will be completed. Budget contingency time for this. Again, management will not be upset if you complete your task ahead of schedule so be generous with your time. In an ideal world, you should have a good idea of how much time it will take to upgrade because of the research you have done during the migration planning phase.

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Since we have been children, the phrase “practice makes perfect” continues to hold true in nearly all aspects of our lives. The same can be said for migrating to a new version of Windows Server and by utilizing development environments to simulate upgrading production systems, not only will this give you a better idea if your time allotments are correct but it will help surface complications that may not have become apparent during the research phase.

Step five —create a backup: This is a critical step in the event that an unforeseen issue forces you to roll back the update process and restore the last known good configuration. You want a restore point that is representative of the last seconds before a production server was pulled offline so that when the restoration is complete, no data was lost.

Step six — document it all: Following a successful upgrade, it’s important to document all steps taken during installation; pain points, configuration changes and the final settings that you used on the new system. While this may seem like a tedious step, your documentation will help any employees who need to replicate your procedures. Or you may need to provision a new server with the same settings at a later date and having a cheat-sheet ready will make the process go faster.

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Migrating to Windows Server 2016 is a big task. With the right preparation and careful planning, you can reduce or eliminate the traditional pain points of upgrading. With software becoming more fluid and features rolling out in faster iterations, it’s important to remain nimble so that software upgrades become a simple process and not an arduous task.

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