Fail to plan, plan to fail: Start looking at your Azure migration strategy now

by | Aug 30, 2020 | Blog

It’s end-of-life for Windows 2008/R2 in January 2020 and that’s going to create headaches for many Australian organisations.

Cuts to IT budgets over the past few years have resulted in IT having to do more with less. And this hasn’t included upgrading legacy operating systems.

From our own CloudLift data we know that 42.4% of servers are running Windows 2008/R2 across a sample of Australian systems, both government and private. The number of Australian organisations still using Windows 2008/R2 is likely to be much higher than even the worrying figures in our data.

What does Windows 2008/R2 end-of-life mean?

Basically, it means that after January 2020 there will no longer be free security updates from Microsoft for 2008/R2. Affected organisations can purchase extended support on affected servers where there is an Enterprise Agreement and Software Assurance in place.

Microsoft are also offering free extended security updates for affected servers when they’ve migrated to Azure. This is a great motivator for organisations to move to Azure, especially as they will then avoid the wasted, probably unbudgeted, expense of extending support on-premises and upgrading applications at their own pace.

So, Windows 2008/R2 isn’t a problem after all, right? Your organisation can simply migrate to the Microsoft Azure cloud.

Wrong. Migrating to Azure can be a major challenge and organisations need to plan for it. For example: which migration model is best for your organisation?

Rehost, replatform, rearchitect: Just three possible migration models

There are actually six migration strategies, commonly referred to as ‘the six Rs’. They are: retire, rehost, replatform, rearchitect, retire, repurchase and retain. In this blog, we will look at three of these strategies: rehost, replatform and rearchitect.

Organisations need to look at all their applications individually and adopt a strategy for each one. Things to consider when selecting a strategy for each application include:

  • Level of business criticality
  • Level of application complexity
  • Application characteristics and business constraints


Rehosting is more commonly referred to as ‘lift-and-shift’. It involves migrating existing applications to Azure without making changes to the underlying application. This is analogous with virtualising physical servers and is limited to infrastructure changes to the application – that is, compute, storage, network.

The scope of activities completed in a rehosting strategy include:

  • removal of on-premises agents
  • deployment of Azure operations agents
  • page file optimisation for Azure
  • configuration of Azure DR solutions
  • implementation of Azure-based security controls to meet confidentiality and integrity requirements

The acceptance testing for rehosting focuses on changes to the infrastructure platform. For example:

  • Does the application server boot?
  • Is the application’s storage in a known and consistent state?
  • Is the application responding to user requests?
  • Is the application licenced?
  • Are integrations to the application operational?


Replatforming is also known as ‘lift-tinker-and-shift’, and seeks to optimise the infrastructure underpinning an application as part of a cloud migration. It maintains the same logical solution architecture on top of a different cloud architecture.

Optimisations may include:

  • upgrading operating systems versions
  • upgrading application platform components
  • adoption of high-value cloud models
  • updating the application version.

The acceptance testing for rehosting focuses on changes to the infrastructure platform and application. For example:

  • Does the application perform as expected on the provisioned Azure infrastructure?
  • Does the application respond to user requests?
  • Are the updated application package and configuration operational?


Rearchitecting involves a rewrite or redesign of an application to use cloud-native solutions. The activities involved in redesign are bespoke and are unique between applications. For this type of migration a detailed assessment of each individual application would be needed to scope out requirements prior to work commencing.

The countdown begins

As you can see, migrating to Azure isn’t a simple process. There’s a lot to think about – and we’ve only covered three of the six Rs in this blog!

Without a plan and a strategy for each application, migration to the cloud will fail and costs will spiral.

At Codify, we understand that migration can seem overwhelming. We specialise in Azure cloud migrations and management and can help organisations to seamlessly manage their Azure migrations. Get in touch with us today as the countdown to Windows 2008/R2 begins.

Ready to connect with Codify to discuss your next cloud project?

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Ready to connect with Codify to discuss your next cloud project?

I know what I want:

I don't know what I need: