Windows Server 2008 and Windows Server 2008 R2 reach end of support on January 14 2020. This means that unless you have a custom support agreement with Microsoft, or unless you’ve migrated VMs running these operating systems to Azure, you will no longer receive security updates related to these operating systems in around 8 months time.


None of this should be surprising to anyone who frequents this blog. Even though we haven’t talked about Windows Server 2008/2008 R2 end of support much here, the end of support date for these operating systems has been public for many years. While more publicity might have surrounded the end of support for Windows Server 2003 and Windows Server 2003 R2 a few years ago, that the clock is running out on Windows Server 2008/2008 R2 shouldn’t really be a secret to anyone.


What’s interesting in the case of Windows Server 2008 and Windows Server 2008 R2 is that, 8 months out from the end of support date, the operating systems are still very widely deployed. When I’ve talked about Windows Server 2019 at conferences around the world and informally surveyed my audience, most in the room will admit to still managing a substantive number of servers running the operating system. (A good number of the audience still admit to having 2003 servers lurking in their datacenters, but let us not open that particular can of worms!)


When I’ve talked to IT Pros as to why their organization hasn’t move to a newer version of the operating system, I’ve received a variety of responses. Everything from a lack of resources to perform the migration, through organizations having bigger fires to put out, to some simply finding that 2008 and 2008 R2 do their job pretty well, so up until this point in time, it’s been hard to make a compelling case to management for the need to upgrade.


Beyond the fact that unless you have a support agreement with Microsoft, you won't get any updates beyond January 2020, there are other good reasons to move to a more recent version of Windows Server. When Microsoft stops supporting an OS, vendors follow suit. It won't just be your OS that's unsupported, but you'll likely find that any applications and drivers you are using with the operating system won't be supported either. Support isn't just a matter of "if it's broken, they won't help us fix it" but is increasingly a matter of "if it isn't supported, we aren't able to meet our compliance obligations" as quite a lot of compliance regulation specifies that workloads must be run on platforms supported by the vendor. The pragmatist's argument "it's not supported, but it still works anyway" is unlikely to pass muster during a compliance audit. While management might be reluctant to release funds on the basis of a technical argument, they might be more willing to open the wallet if not doing so might lead to compliance headaches.


What we’d love at IT Ops talk to hear in the comments of this post is, if your organization hasn’t migrated from Windows Server 2008 or Windows Server 2008 R2, why you think that’s the case? Are there resources we can provide for you that would assist you with the process? If you have Windows Server 2008/2008 R2 deployed, is end of support something that you’re actively worried about, and if not, why not?

Super Contributor

Admins are too busy updating Windows 10 every 6 months and dealing with updates issues :) Seriously though lack of time and resources is the main thing. Many SMBs are understaffed in IT. On my last job we had 2 infrastructure admins for 200+ users and dozens of systems and hardly were able to keep up. I have recently been in an interview and 120+ users company with huge office and 15 laboratories wanted one guy to look after. SMBs still don't see IT as an important thing.


Do you think that there's anything that Microsoft can do to help people get off 2008/2008R2 beyond what's already being provided?

Super Contributor

Reveal some nasty unpatched vulnerabilities after the support end :D

I think the only thing Microsoft can do is educate (seminars, through partners) and i think this is already happening and most admins know that. Maybe some discounts for upgrades, at least in the public sector.

We have used 2003 Server 1 or 2 years past support because hardware we owned only worked with that version and we didn't have a budget to replace that hardware. When i was leaving my last place they had around ten VMs with 2008/2008R2. Last time i spoke with them a few months ago they still had at least one of them running. Some should be easier to move, but for some i just can't imagine them ever doing that. One farm with 6 servers of highly customized SP2010, which is a huge task to even port to 2013/2016 (not even mentioning SPO). And this is the main LOB app. One 2008 server with the main finance management app made my a not so cooperative local provider with 10+ years of customization, libraries, frameworks, etc. And it can't be stopped for a day or so. And one somewhat new admin and another one completely new.


I believe the SharePoint Migration Tool https://docs.microsoft.com/en-us/sharepointmigration/introducing-the-sharepoint-migration-tool?WT.mc... only supports SharePoint 2013 and later rather than 2010 - also necessary of course to migrate the underlying infra stuff such as SQL as well when upgrading SharePoint.


I've had a few people tell me the reason they are stuck on Server 2003 was a dependency on some code that only worked on SQL 2000. VMs running 2008/2008 R2 should be upgradable to 2012/2012R2 (and at least with a VM it's relatively straightforward to create a disposable clone and see if the upgrade breaks anything.

Complicated Vendor software I think is the big stopper, it's painful and drawn out to move it to another updated server or servers. I don't know how Microsoft can help at all with this because Microsoft isn't the problem :)

Senior Member
Ditto to Adam. The infrastructure that my co-workers and I are responsible for already moved to 2016/2019 for the most part. A few "old" things are on 2012/2012 R2. Everything on 2008/2008 R2 is stuff that we host for vendors, sub-departments with internal support, etc. These are nigh impossible to move because either A) vendor support is lacking, B) vendor no longer exists, C) time/resource constraints keep the responsible parties from acting, or D) moving away from 2008/2008 R2 involves buying new hardware or entering new, cost-prohibitive support contracts with vendors. Microsoft can't do anything about that.
Super Contributor

Well, Microsoft can do one thing. Prolong the support. Although they probably won't do it.

Occasional Visitor

I work for a Managed Service Provider that also works with quite a few break-fix clients.  For our managed clients, we work with them to create an IT budget and a plan to bring them to a supported world before the January 14 2020 D-Day (replace 2-3 legacy windows machines a month for instance) and even do much of the legwork at trying to get legacy software (vendors that may not even exist anymore) running on modern operating systems when possible.


Aside from legacy software compatibility, the core problem is that many companies do not have an IT budget and fail to plan.  These small businesses undervalue their IT infrastructure and have the mistaken mentality that “if is working, why change it?”  


If I approach an unmanaged break-fix client with no IT budget they balk at the cost of:
1) New server. “Why can’t I just keep using my 10-year-old server?”
2) licensing costs (Server, Cals etc) For instance an SBS 2011 client who still has to keep email on premise that now has many more licenses to consider
3) Cost the vendor charges to migrate their line of business application or, in most cases, the cost to renew their long-expired support contract that they decided to not renew after their last upgrade was complete. (One vendor wants them to pay for every year prior)
4) Labor cost to perform the actual domain, exchange and file migrations.

If a client has an IT budget and plans accordingly, these do not become issues. 



The most common reason I hear is "we are waiting on the application developer", whether that's an in-house legacy app or a third party vendor. For vendors who have not brought an app up to scratch yet, there's a cost to the customer to find & migrate to an alternative application, so most customers sit & wait for an app upgrade instead.