Is Upgrading Windows Server 2008 Before End of Support Worth It?

by | Nov 14, 2019 | Managed Services | 0 comments

Windows Server 2008 Upgrading to new technology can be challenging in any form, particularly when dealing with enterprise-scale issues, like deciding what server operating system to use. Yet with the Windows Server 2008 end of support date approaching on January 14, 2020, businesses should highly consider upgrading to Microsoft Office 365 beforehand. After the Windows Server 2008 end of support date, Microsoft will no longer provide security updates and technical support for the product.

Windows Server 2008

Why Should I Upgrade Windows Server 2008 Before End of Support?

Maintaining the status quo may seem like the easiest way to go; however, failing to upgrade before the Windows Server 2008 end of support date can leave your server vulnerable to attacks. Normally, Microsoft will send security patches when it identifies a security hole in its products, yet after the Windows Server 2008 end of support date, users won’t receive those updated for that version. As such, cybercriminals may be able to recognize a weak link in your network and hack in, and there won’t be a fix readily available to you.

After Microsoft ends support for Windows Server 2008, it will stop sending out product upgrades. You won’t receive new features, and over time, your ability to manage your server using this product will become less practical. Further, Microsoft will no longer offer technical support for Windows Server 2008 after its end of support date, which may affect your business if you experience troubleshooting issues.

These risks are analogous to what Windows 7 users will face after end of support, which also falls on January 14, 2020. Organizations that use Windows 7 along with Windows Server 2008 after end of support would thus be putting themselves at an even greater risk for cyberthreats and limited functionality.

Windows Server 2008

Possible Workarounds in Response to Windows Server 2008 End of Support

While you may recognize the risks inherent in using Windows Server 2008 after its end of support date, many businesses try one of the following tactics so that they don’t have to completely overhaul their server software:

  • Separation: With the separation workaround, you could take the Windows Server off of your network to try to avoid it being infiltrated. The server would only be used for non-critical activity, like managing thermostats or a door system, rather than critical functions on the main network. This way, if the server is hacked, the business as a whole wouldn’t be in imminent danger.
  • Isolation: Another option is isolating the server and only allow activity to pass through one reliable and heavily secured pathway, such as a firewall. However, this workaround can require expensive technology purchases and detailed oversight to guard the data flow to and from the server.

At the very least, businesses using Windows Server 2008 after the End of Support date should cut all integrations with Windows 7 to limit the risks of not having security patches, upgrades or support. You should really only consider these options if you need to buy some time for an ideal window to perform an upgrade.

Even with these workarounds, keeping server software running after its EOS date does not eliminate risk; upgrading is still the far safer option. Hackers are experts at identifying weak links in the network, and end-of-support technology is like a homing beacon for bad actors looking for a way in.

Windows Server 2008

Upgrading for Higher Security and Lower Costs

While these workarounds may seem appealing to those looking to minimize expenses, neither option is more cost-effective than upgrading to Office 365. Firewalls and third-party security technology can be expensive, and a data breach can be far more costly than the price of your server operating system.

Instead of exposing your business to this risk and long-term costs, migrating applications to Office 365 is the more reliable and efficient solution.

Working with a certified Microsoft partner like Peters & Associates can make the migration to Office 365 significantly easier. We have deep experience across Microsoft products and can help you upgrade your server and reconfigure your IT architecture as needed to accommodate new software according to your needs.

Get in touch with Peters to learn more about your options for upgrading from Windows Server 2008 before its end of support date, and learn more about how you can prepare for other upcoming Microsoft end of support deadlines in our end of support overview.