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Windows 2008 Server End of Life: Here’s What You Need To Know

Windows 2008 Server End of Life: Here’s What You Need To Know

There’s been a lot of news out of Microsoft lately, regarding their termination of legacy platform support. It’s interesting, considering the last time this happened (with the termination of XP and Windows 2000), there was a surprising lack of pomp and circumstance compared to this time around. It’s so odd because these were very ubiquitous platforms, even well into the Server 2008 and Windows 7 days, possibly more so than those two platforms are at the moment.

The difference is that threats to deprecated operating systems are so much more severe now, with the consequences of not upgrading being quite significant. Hackers and other malcontents are faster thanks to the speed with which GPU-enabled computing and brute-forcing are achieved, meaning the absence of ongoing security updates and patches is almost instantly disastrous to users who don’t stay up to date.

This is what awaits people after January 14, 2020, when Windows 7 and Windows Server 2008 R2 become officially unsupported.

But Why?

Why does this happen, I hear you ask? It’s easy to forget that software is a product, the maintenance of which is an ongoing expense for the provider. Like automobiles, once the technology driving a product is too obsolete to be profitable, it stops making a lot of sense to continue pouring money into trying to keep it functioning within normal modern parameters.

Microsoft aren’t heartless, though – they will often support a platform for several years beyond the arrival of a successor, as has been the case with these two operating systems. They understand that upgrading often brings with it expenses, disruption, initial technical problems and of course, probably some training for the users. They also have learned from experience that their newest iteration of a product isn’t guaranteed to be a success (ME, Vista and 8, anyone?). So, there is a buffer period while they let the new product come into its own and prove itself, and allowing companies to take their time smoothly transitioning to new technologies.

Sooner or later, they have to pull the plug on the outdated technology. This serves two purposes – one is the aforementioned termination of unreasonable wasting of resources, the other is that final push some users and businesses need in order to get them to make the transition. It’s often for their own benefit anyhow, with proven new systems having benefits beyond just being still-supported.

What does No Support Mean for Me?

Your next question will understandably be, what does this termination of support mean for your business? Will your operating system just stop running? Will it no longer activate if you need to restore it? Is this the apocalypse?

It’s severe, but the disaster doesn’t quite take that form. Your system won’t shut down, it’ll still activate (for now) if you reinstall it, you can even still purchase licenses for it (though it’s discouraged to license old software). The disaster comes from the fact that Microsoft simply won’t be providing updates for Server 2008 R2 anymore. No new features, no new bugfixes, no new security updates will ever be made by Microsoft again.

Within days, lurkers out there waiting for this opportunity will begin to map the remaining exploits (which will never be fixed), and everyone running this old system will be vulnerable to all manner of chaos. I wish this was hyperbole, but it’s happened in the past, and it will happen this time as well.

You’ll also have a rougher go of getting tech support from Microsoft when something malfunctions with Server 2008 R2, though some level of this will be available for an as-yet unannounced price. Count on it being subpar support for a ridiculous price – this is another intentional strategy to get you to abandon outmoded software, not them being jerks.

Is It Worth It?

So, you remember the headache of upgrades – especially server-side systems – in the past, and you’re wondering if the peace of mind and newness of the system is worth this hassle, when you could probably have third-party patches installed or made.

It is absolutely worth it, especially in the case of Server 2008 R2. In fact, seeing as it’s being terminated on the same date as Windows 7, it’s almost serendipitous. If you upgrade your servers first, with Server 2012 or 2016, you can use distributed update and asset control to very, very seamlessly upgrade the workstations from 7 to 10 (we’ve talked about this one in fact). Do not go the route of life support via 3rd party tools. It’s a rabbit hole, trust me.

How Do I Prepare?

So, while this upgrade is painless, and your hardware is probably fine for the newer systems (server hardware gaps are minuscule compared to workstation specs), it’s always, always a good idea to do the 3-2-1 backup strategy (three copies on two different media).

You should also schedule around some downtime as the upgrade takes place and your IT infrastructure may stall. If you’re using cloud-based or offsite services, this upgrade has probably already happened without you even noticing, by the way.

If you don’t have Microsoft’s Software Assurance policy, you will need to either purchase a copy or license an upgrade, which installs pretty much as seamlessly as the Windows 10 upgrade. 2016 especially shares most of the same code, just with an IT focus and more transparency where this needs to exist, after all.

The Bottom Line

The bottom line is, while your system won’t shut down on the 14th of January, you’re basically running through wolf-infested woods with porkchops strapped to you at that point, if you don’t upgrade. This upgrade is simple, but we’re of course here to help it run much more smoothly. Remember, you’re not alone in the technology world, not with us around.

If you’re running old software, don’t panic, fill out our contact form today. We’ll answer all your questions, we’ll look closely at your environment, and we’ll help you prepare for a seamless upgrade that will keep you secure for the upcoming decade!