It’s been on the horizon for a long time, and now, it’s finally happened: Microsoft has announced the end of free product support for MS Windows Server 2008 and 2008 R2. As of January 14, 2020, customers will no longer receive free upgrades or extended support services.


windows 2008 R2 end of support


For a lot of small and medium-sized companies, the urge to panic might be irresistible. According to a pair of 2017 surveys of the marketplace, 8% of all Server 2008 and 2008 R2 customers globally were in the UK, the majority being businesses with less than 1000 employees.

There are tens of thousands of businesses in the UK still running Windows Server 2008 / R2 – are you one of them? The potential for severe problems if the transition to a supported version is not managed correctly ought to be evident. But what’s a company to do?

Contact us



Why Not Leave Things Be?

End of support, means, quite simply, the end of protection. The cessation of security upgrades will leave companies and their customers vulnerable to cyber-attacks. What’s more, the end of support means the end of innovation. Websites and apps will begin to look outdated, and a company could soon look like it’s part of the “Dead Web.”

General Data Protection Regulations (GDPR) requirements in the EU also make updating servers essential. 2008 standards for protecting personal information will no longer be sufficient. If companies do not keep up, they’ll run into legislative issues.

Failure to act is not an option.

Migrate Windows Server 2008 and Windows Server 2008 R2 to Azure

Luckily, Microsoft Azure has arrived. Compete 366 can help you achieve a smooth transition from Server 2008/2008 R2, at minimal cost and disruption.

Microsoft is offering three years of continued product support for free for Server 2008 and 2008 R2 users who transition to Azure. That makes Azure, with its wide variety of state of the art apps and solutions, the obvious choice for small and medium-sized businesses eyeing the calendar as January 14, 2020 gets closer.

However, we’ll look honestly at the options on the table first.

Three Choices (Only One Good One)

Upgrade Now: You could decide to move into an upgrade of your operating system to Windows 2016. If you have Software Assurance, and your apps support later versions, you might conclude that now is the time to upgrade. It’s a decision you might make anyway, but it is being rushed by circumstances somewhat. Depending on what kind of year you’re having, the bottom line might not support such a move right now.

Leave It Alone, Pay for Support: You could leave your servers as is, and pay for extended support from Microsoft to continue. That’s a simple, yet an expensive solution. And you won’t have access to the innovation that comes with Azure.

Migrate to Azure: You can migrate to Azure, getting three years of extended support for free. You’ve gained continued security upgrades, innovative apps and solutions, and time to consider future moves without being rushed by a deadline that’s less than a year away.

Options for Migrating Windows Server to Azure

If you’ve decided to migrate to Azure, there are a further three options, depending on your existing configurations, and plans for the future.

Build a New Server on Azure Marketplace: You can build a new 2008/2008 R2 Virtual Machine (VM) from an Azure Marketplace image. This is a pure, low risk, solution. Just install the software, and copy over your data. Now, you’ll have a clean Azure image.

Upload a VHD to Azure, and Create a VM from it: If your servers are virtualized (Hyper V or VMware), you can upload a VHD and create the VM from that. Bear in mind that Azure only supports Generation 1 VMs with VHD file format and a fixed-size disk. The maximum VHD size is 1023 GB.

Use Azure Site Recovery (ASR): Regardless of whether your servers are physical or virtualized with Hyper V or VMware, you can use ASR to migrate them. Though it can be more complicated than the first two options, using ASR has a couple of benefits. First, ASR is useful for migrating complex workloads with little downtime. Also, ASR is free for the first thirty days.

The Benefits of Migrating to Azure

If you’re still not sold on migrating to Azure, consider four main benefits of making a move:

Security and Compliance: Azure helps companies maintain cybersecurity and meet regulatory requirements like GDPR. Some key features of Azure in this category are:

Azure SQL Database Intelligent Protection: Proactive, 24/7 threat monitoring and response.

Azure Security Centre: Monitoring and alerts 24/7 across all applications.

Azure Governance: Provides blueprints for regulatory compliance across all services.

Consistency in Hybrid Cloud Computing: Azure is the only genuinely consistent hybrid cloud, due to features like these:

Identity: Azure connects all your directories to maintain brand consistency across apps and services.

Windows Admin Centre: Easy, five-step backups thanks to Azure Recovery and Azure Backup.

-Azure File Sync: Allows bottomless file storage.

Cost-Effectiveness: With its nearest competitor, AWS, costing five times as much, Azure is in a league of its own here:

-Azure Hybrid Benefit and Reservation Pricing: Customers who migrate to Azure can save up to 55%.

-Free Extended Security Benefits: Server 2008 and 2008 R2 customers can have peace of mind for no extra cost.

Innovation Tools: A visit to the Azure Marketplace should reinforce the point that Azure offers unmatched innovation in computing. Consider just three examples:

Azure IaaS

-Azure SQL Database

-Azure App Service

Make the Move

Azure offers the secure, consistent, cost-effective, and innovative solution for Server 2008 and 2008 R2 users. January 14, 2020, can’t be put off forever. Contact us for a free consultation to discuss your options, and make the leap to Azure.

Let's Talk

    Enter your details below and we'll be in touch soon:

    Published On: January 31st, 2019 / Categories: Azure /

    Contact our Microsoft specialists

    Phone or email us to find out more – or book a free, no-obligation call with our technical consultants using the contact form.

    “It’s great to work with the Compete366 team, the team members are really knowledgeable, helpful and responsive. No question is too difficult for them. They have really helped us to manage our Azure costs and ensure we have the right environment. When we bring a new customer on-board we can scale up immediately via the Azure portal and quickly make environments available to our customers.”

    “We also find that there’s never a heavy sales pitch from them – they are technically focused and recommend what’s right for us.”

    Paul Coyne, Rusada

    “We had great support from the Compete366 AVD expert, who was really helpful, and guided me through options to tackle issues that arose.”

    “The great thing about our AVD set up is that we have a custom set up for each project which Compete366 showed me how to do. And with the scalability and flexibility of AVD – we can meet clients’ expectations and get project users up and running more quickly.”

    Amir Dangol, Senior IT Manager, Integrity

    “We were immediately impressed with the advice that the Compete366 specialists in Azure Architecture were able to provide. This was all new to us and we really needed some external expertise that we could use to get our questions answered. The beauty of working with Compete366 is that we transferred our Azure consumption to them, and at the same time received all of their advice and guidance free of charge.”

    Tim Entwistle, Head of Software Development, Herrco

    “Working with Compete366 has been like extending our own team – they are extremely and easy to work with. Right from the outset, it was clear what was on offer – everything was presented to us in a straightforward and uncomplicated way. They also provided just the right level of challenge to our developers and saved us time and money by suggesting better ways to implement our infrastructure.”

    Oliver Mackereth, Project Director, Hanse

    “Compete366 were able to help us leverage some useful contacts in Microsoft. We really value the expert advice and guidance that they have offered us in setting up a highly scalable infrastructure. We are also setting in place a regular monthly meeting which will allow us to further refine our architecture and ensure we keep on track as our requirements grow and change.”

    Matt Brocklehurst, Technical Director - AWOL Adventure

    “I have been delighted with the migration, where my team worked very hard, supported by expert advice from Compete366, and achieved everything in the timescale we had set out. Compete 366 made sure that we didn’t make any expensive mistakes, and guided us through the process”

    Darrell Cann, Managing Director, APEX
    Jon Milward

    By submitting your details, you agree to be contacted.