Windows Server 2008 End of Life: 5 Migration Tips

Most businesses know the perils associated with running outdated software such as security vulnerabilities, reduced productivity and increased maintenance costs. Almost every software system has rolling End of Life (EOL) dates where updates and support ceases. Microsoft is no exception with upcoming EOL dates impacting everything from servers and operating systems to browsers and productivity software.

One that should be on your radar is January 2020’s EOL for Windows Server 2008 and Windows Server 2008 R2. If you haven’t already, it’s time to start exploring migration options so you don’t put your applications and infrastructure at risk (January 14th, 2020 will come faster than you think).

Looking to the Cloud

Some of the first questions you should be asking are about how to handle your data centre requirements in the years to come.

  • On Prem: Do you want to retain an on-prem data centre? This could require more than a software upgrade if the servers are more than five years old. New hardware might be needed too.
  • In the Cloud: Is it time to move to the cloud? Many organizations see EOL for Windows Server 2008 as an opportunity to join the many businesses already in the cloud – whether that’s extending the number of cloud-based applications, migrating completely to a cloud provider like Azure and/or taking advantage of the features and benefits of Office 365.
  • Hybrid: Does a hybrid approach make sense for your business? Are there some functions or workloads that might work better locally or data that you want in-house for increased security or archival purposes?

There’s no one-size-fits-all approach when looking at your data and application needs, so it can help to get external input as you investigate your options.

Getting Ready for Software Migration

Once you’ve decided on the approach that makes sense for your business, there are some important steps to help your migration go smoothly.  Here are a few we think are critical:

1. Clean Up: You wouldn’t move a house without taking the time to sort through your belongings and get rid of things you don’t need. The same is true when moving your data. You don’t want to pay good money to store your garbage.

  • Look for duplication.
  • Evaluate your content – how is it used, how often, do you need to access it regularly?
  • Identify content that can be archived as you might want to consider alterative storage arrangements.
  • Review your information architecture and content structure. Use this opportunity to update or refine it to boost efficiency.

2. Prepare for Change: Implementation of any new technology represents a change for the users, so you need to take the time to create protocols for your cloud environment including governance, collaboration and file structure. Map out your new processes and make sure everyone understands them.

Next, you need to focus on training. Working in a cloud environment is also a big change for some users so dedicate resources to training so everyone knows how to best use the new environment, follow corporate protocols and policies, and leverage the feature-rich tools in software like Office 365. You might need to address some basics such as ensuring users know they don’t need to save files on both their local drive and cloud drive, or that they can collaborate with team members on documents in real-time by sharing a link instead of forwarding files.

3. Plan it Out: For IT staff, take the time to map out how the migration will be structured, answering questions including what applications to move, how many users to move at a time and which users get moved when. You might, for example, have 100 applications and decide to move 10 at a time using the experience gained during the move to improve results on the next one.

Every company will have a different timeframe to phase in a migration, just ensure you have a clearly articulated strategy and workplan to guide you. Regardless of whether you plan to transition over days, weeks or months, remember that the longer your migration timeframe, the longer you’ll have two systems to monitor and maintain.

4. Set it Up Right: Before you start moving any applications or data, you need to configure the cloud environment and the applications, including setting and testing security so you don’t have a back door open to hackers when your data starts moving in. While cloud service solutions and Office 365 tools seem easy to set up, it’s important to take the time to review configuration settings and adjust them to suit your corporate governance and protocols.

5. Moving Day: There are different approaches for migrating applications and data from simple copy and paste to using tools to map old content and data to a new information architecture. Whether you are moving a part or the entire content of your company, migration and testing is the final stage before users get their hands on the new system.

Migration’s Helping Hand

Companies that have never migrated to the cloud or started using cloud-based applications might struggle in the beginning.  It’s worth talking to experts who’ve done it before because, although the steps might seem straightforward, experience can help you avoid costly configuration mistakes or errors during migration that can put the entire project at risk (which we’ve seen before). No one wants to start from scratch after beginning to make such a big move.

Whitecap has a full range of services from planning and auditing, to design and infrastructure architecture. Our team also has the technical skills to prepare data for migration, set up and secure your cloud and Office 365 environments, deploy migration tools or build customized scripts to map and transition content from the old to the new system. We can help you with part or all of the migration process.

Making the transition to the cloud and to Office 365 can be a lot of work, but you will reap big benefits from a modern infrastructure that can support the business needs of tomorrow.

Is your business running Windows Server 2008 or another software reaching end of life? Let’s talk about application modernization strategies that fit your needs.