In 16 months Windows and SQL 2008 and 2008 R2 will no longer be supported, what’s your plan?

Let’s not kid each other, you or someone you know is still running Windows Server 2008, 2008 R2, or SQL 2008, 2008 R2 in production. I’m not trying to say you (or them) are a bad I.T. person because of it. Some applications are either so outdated they can’t be upgraded or they are just a huge pain in the a$$ and you have been putting it off. Consider this post an intervention, because it’s time to make a decision.

What are your choices?

These platforms are already in what Microsoft calls the “Extended support” phase, but that too will soon expire.

  • Extended Support for SQL Server 2008 and 2008 R2 will end on July 9, 2019.
  • Extended Support for Windows Server 2008 and 2008 R2 will end on January 14, 2020.

If you still have these in production you have two choices:

  1. Migrate your system to something newer before Extended Support runs out.
  2. Purchase Extended Security Updates if your migration will take longer than the deadline.

One way or another it is time to upgrade. The real question is how long will it take you.

What are extended Security Updates?

Microsoft has an FAQ PDF document here that explains in detail what is available if you plan to keep one of these platforms past the dates above and purchase Extended Security Updates.

In summary:

What do Extended Security Updates include?

For SQL Server 2008 and 2008 R2: Extended Security Updates include the provision of Security Updates and Bulletins rated “critical” for a maximum of three years after July 9, 2019.

For Windows Server 2008 and 2008 R2: Extended Security Updates include the provision of Security Updates and Bulletins rated “critical” and “important,” for a maximum of three years after January 14, 2020.

  • This offer does not include technical support, but you may use other Microsoft support plans to get assistance on your 2008 and 2008 R2 questions on workloads covered by Extended Security Updates.
  • This offer does not include new features, customer-requested non-security hotfixes, or design change requests. However, Microsoft may include non-security fixes as we deem necessary.
  • There is no retroactive effect for any update that the engineering teams declined in the past.

So basically if something crazy happens and it’s critical enough for Microsoft to patch the problem… you would get that patch.

Do you want to pay for extended security or get them for free?

Microsoft has a new program that benefits both you and them. (Remember Microsoft is all about one thing… Spinning the Azure meter faster than an electrical meter at a Chinese Bitcoin mining farm.)

If you want to read the full offer check out this link. In summary, Microsoft will give you (for free) Extended Security Updates for all workloads that you move to Azure for 36 months!

If you aren’t ready for Azure, then Extended Security Updates will cost you 75% of the price of NEW licenses. (Meaning that if SQL 2017 costs 10,000 … extended security will be 7,500).

Bottom line… if you have been thinking about dipping your toe in the public cloud space… this is a pretty sweet deal… and now is the time to start.

Getting to Azure

It turns out that Zerto is able to move these legacy workloads to Azure with ease. Trust me, I tested it; and I will be posting an article soon on how to prepare a Windows 2008 and Windows 2008 R2 server for migration to Azure. (There are some pitfalls)

Once you get to Azure it’s time to think about what the end game is. Do you create a Windows 2016 (or Windows 2019) server VM, then install SQL server 2017 and migrate the databases? Or do you start using PaaS and migrate the databases right to Azures SQL platform as a service?

The choice is yours, either way, the advantage of having your existing legacy SQL server in Azure is clear: When it is time to migrate you will have the fastest possible connection to the PaaS service, or to a new Windows 201x VM. (I put “x” because depending on how long it takes you Server 2019 might be out.)


Normally I don’t write articles about management-level stuff like this (That’s normally Sean Master’s job). But this article is a precursor to a few posts that I have queued up that are technical.

Migrating to Azure can be as simple or as complex as you make it. Using Zerto obviously helps to get VMs into Azure IaaS, but there are still some tips and tricks worth sharing. Those are what my upcoming articles will be about. I have learned a lot about Azure and migrating to it in my Tech Alliance Architect role at Zerto, and hopefully, that experience will make your life a lot easier!

If you would have asked me a couple years ago if I was for putting servers in the cloud, I would have told you hell no. That is still my stance for some workloads too, like the ones that need to be connected to manufacturing equipment or for facilities where Internet connectivity is sketchy. Outside of that stuff though, I see no reason not to leverage IaaS and PaaS platforms like Azure, AWS, and GCP.

As a side note, I think that if you are in the “I build data centers with a hypervisor and hardware” game, I think it’s time to get some public cloud skills, because like it or not, cloud won’t be going away and the market for customers wanting hardware will continue to shrink over time. (You have to ask yourself: if I’m not having the public or hybrid cloud conversation with them… who is?)

So stay tuned, and hopefully, I can share some stuff that will help you make the migration to Azure easier.


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