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January 17, 2020
End of Support for Windows 7, Server 2008 and SQL 2008 – What to do?

So, the day has finally arrived. Microsoft has officially released the last patches for the Windows 7 and Server 2008 families. SQL 2008 has ended support as well, but not many folks talk about it. And they released some doozies to go out with a blast. So, what do we do now?

For those of you that were able to retire all of the systems running these operating systems before the deadline, it’s business as usual for you. No fireworks, no fanfare, maybe a pat on the back for all of the hard work required to get there.

For those of you who have not crossed the finish line yet, there are many possible paths, but the clock started ticking on Tuesday of this week. You effectively have until February 11th to get your ducks in a row. Moving forward the only patches for those OSes we can expect would be extremely rare cases like MS17-010 – the infamous WannaCry patch. So, let’s look at that example and find out why not having support for an OS really matters.

Sure, you can’t open a support ticket with Microsoft for issues on that OS, in general this is no big deal for most people. The big problem here is that it seems that when there is a critical vulnerability on a Windows operating system, that the problem frequently runs across all the operating systems.  So when a patch is released for a specific vulnerability, bad guys can frequently reverse-engineer the patch to find out where the hole is that is being plugged. Once they know that, then they can simply look at the operating systems that are no longer supported and see if the same hole exists there – and it frequently is. Then, it is only a matter of time before the bad guys write some code to exploit the hole. That’s really high-level and basic, but that is the general premise of the risk to the environment. If we look at WannaCry, Microsoft released patches for XP, which was way out of support, to close that hole.  They knew the NSA’s toolkit got left on a park bench and the bad guys got a free skills power-up overnight. Same general premise, but the toolkit just shortened the timeframe required for the bad guys to be able to exploit it.

Again, the clock is ticking. When the next set of monthly Microsoft “Patch Tuesday” patches are released, the bad guys will get busy trying to find out what they can exploit on Windows 7/2008. With the crypto-related patches released this month, if Windows 7/2008 would have already been out of support, I would expect Microsoft to have released them for Win7/2008 as well – it was such a potentially catastrophic vulnerability.

Something like this will happen again. Some critical vulnerability will be exposed at some point, and the bad guys will exploit it on non-supported operating systems. Predicting this doesn’t take some mystic seer – just some basic common sense.

So, you realistically only have a few paths that you can take from here.

  • Work tirelessly to get rid of the last of the Windows 7 and Server 2008 systems in your environment.
  • Write Microsoft a check and pay for patches. If it will take you a while to remove these systems in your environment, and you can scrape up the budget, this is the best choice. I don’t like writing Microsoft big checks anymore than anyone else, but this is a business decision. How much risk is the business willing to accept?
  • Isolate anything that you can on the network. Leverage all of the other layers of protection that you hopefully have in place to protect. There are still companies running Windows XP and Server 2000/2003 because they simply cannot change that portion of their environment. Those companies isolate like crazy.
  • Stick you head in the sand. Oh, and if your end-users are running Windows 7 and they have admin rights, don’t worry – your head probably won’t be stuck in the sand for too long.

So, get off of them if you can, or pay the piper for more patches, or wait and possibly pay the consequences.

For those of you with enterprise patch management tools, some vendors will allow you to purchase support to support the deployment of the patches you purchased from Microsoft. BigFix is one of those tools. For those of you not familiar with BigFix, reach out and let’s talk. Wicked powerful set of tools that go way beyond the patch – true configuration state management tools.

BigFix recently released an announcement stating they will offer paid content to complement the patches you paid Microsoft for. This content keeps things business as usual. Very affordable as well – $10k per OS flavor (Win7 or Win2008) per year. If you have 100 Windows 7 systems or 10,000, the price is the same from BigFix for the extended support content. Again, you still have to write the check to Microsoft.

Like I said earlier, this is simple math – how much risk is the organization willing to take on before they decide to open the wallet?

If you need help – let us know.

Useful Microsoft Extended Security Updates links:

Link to HCL BigFix Blog for Extended Security Updates

https://blog.hcltechsw.com/bigfix/bigfix-offers-fixlets-after-end-of-support-for-windows-7-and-windows-server-2008/

About the Author
CBI | Cybersecurity Solutions
CBI Cybersecurity
CBI is a leading cybersecurity advisor to many of the world’s top tier organizations. Founded in 1991, CBI provides innovate, flexible and customizable solutions that help ensure data is secure, compliant and available. We engage in an advisory-led approach to safeguard our clients against the ever-changing threat landscape—giving them comprehensive visibility into their entire security program and helping them avoid cyber challenges before they can impact their data, business and brand. We are dedicated to the relentless pursuit of mitigating risks and elevating corporate security for a multitude of industries and companies of all sizes.
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