itSynergy: Blog

Microsoft Windows Server 2008 End of Life

Hackers Have Windows 7 & Windows Server 2008 End-of-Life Plans. What are Yours?

Zero-day exploit: The details of a software bug are released to the public before the manufacturer has a chance to fix it. Hackers exploit the flaw, harming your business with malware or accessing confidential data.

When Microsoft Windows Server 2008 and Windows 7 enter End of Life (EOL) on January 14, 2020, every day has the potential to be a zero-day exploit because Microsoft isn’t going to provide security patches or updates.

You Can’t Afford to Ignore Microsoft End of Life

You may be tempted to procrastinate, but hackers won’t lose any time. The confluence of businesses not preparing and support ending for Server 2008/Windows 7 is a perfect storm. As much planning as Microsoft has done to make business owners aware of Windows Server 2008 and Windows 7 end of life, hackers are doing the same level of planning for their zero-day threat opportunity.

After EOL, hackers will be able to manipulate security flaws and businesses will have little ability to stop them. Once inside your network, all client, customer and business data on your server will be an open book for hackers to see, steal and sell on the Dark Web. Additionally, your systems are an easy target for malware and other Trojan horses like spyware and adware, preventing your business from operating normally and jeopardizing your reputation.

This is the danger you will live with every day after January 14, 2020 if you continue using Windows Server 2008 and Windows 7. Even if you avoid hackers your organization won’t meet regulatory requirements like FINRA, HIPAA or PCI because you cannot prove that your data is secure.  

EOL is a real threat. Delaying is not an option.

5 Best Practices for a Seamless Microsoft Windows Server 2008 and Windows 7 End-of-Life Migration

To avoid security and compliance liabilities, you need a cohesive EOL strategy. Here are 5 best practices any small business can follow for a smooth and stress-free migration.

1. Start Planning ASAP

EOL migrations involve balancing multiple schedules. You need to consider your own business cycle and the availability of your IT partner and any other vendors using your Microsoft software, such as line-of-business applications. If you don’t plan your migration appropriately, it could occur just as some critical business process becomes due and you’re at your busiest. An accounting firm may have to wait until the height of October tax deadlines.

Tip! Count on a 60- to 90-day planning period and factor this into your migration timeline.

2. Select a New Operating System

The automatic reaction often is to move to the most current release, which would be Windows 10 and Windows Server 2019. Windows 10 was released in 2015 and is a reliable product we’ve migrated clients to countless times. But we’ve experienced issues as we’ve implemented Server 2019 internally at itSynergy. We recommend Windows Server 2016. It is a more stable offering and the end-of-life date isn’t until 2027.

3. Check Applications for Compatibility

Updating your workplace operating system is not like downloading a new version of an app on your smartphone. You need to ensure that every application you currently rely on will work with Windows 10 and/or Windows Server 2016. You want to upgrade older line-of-business applications so they continue to work with the new system.

4. Discuss Upgrading Hardware

Our focus is not on selling you new hardware, but on having a discussion about whether or not upgrading makes sense for your business.

For instance, if you have a machine that can run the new operating system you may not need to upgrade. However, if the machine is over 5 years old, you may want to invest in new hardware now rather than sink time and effort into a device you’ll replace next year.

5. Limit Downtime

One of the biggest concerns small business owners have during migrations is the potential loss of productivity. As long as proper steps are taken, downtime can be minimized.

An experienced IT partner can move your organization to Windows Server 2016 and Windows 10 without your employees ever noticing. At itSynergy our process is so fine-tuned we can come in after your employees leave on a Thursday, transition everything to the new server and no one will know the difference when they come to work on Friday.  

We favor migrating on Thursday rather than over the weekend. If any issues occur we can promptly resolve them on Friday, allowing you to start the following week with no unexpected delays.

If an employee’s desktop wallpaper was a photo of their kids, we make sure that photo is the wallpaper they see when they come to work after the migration occurs. It is a small factor in the overall migration, but it minimizes the psychological impact of the change and helps your team return to pre-migration productivity levels more quickly.

Have questions about Microsoft Windows Server 2008 or Windows 7? As a Microsoft Silver Partner, we’ve demonstrated expertise in managing migrations and can provide additional information and strategic IT advice. Contact itSynergy today at 602-297-2400 or online.



itSynergy has been providing managed IT services and outsourced technology management to small- and mid-sized businesses for over 20 years. We are seen as trusted technology advisors by clients because we partner with them for success. Our philosophy is that when technology works as it should, it supports and enhances an organization’s ability to accomplish its goals and objectives and meet business growth goals.