Microsoft Windows: End of the World (Support)

Companies like yours need to keep up with strict business, compliance and industry regulations. New threats have made it harder than ever to secure data and applications. With end of support for Windows Server 2008 (including R2) and Windows 7 operating systems approaching, the time to prepare is now, not in December. Waiting will not make it go away.

Although you can certainly make logical arguments upgrading and modernizing applications should and will lead to improved capabilities and efficiencies for end-users, in this case not upgrading introduces significant risks to the company.

End of support means the end of critical security updates, opening the potential for business interruptions. Worse still, without regular security bulletins it is impossible to guarantee protection against hackers or malware.

Unfortunately, the technology world still communicates in technical terms not easily understood by the business community. This is still the case with Microsoft’s announcement regarding the end of support for products. Simply stating an end of support date looming for Windows Server 2008 (including R2) and Windows 7 doesn’t mean it resonates with the business community using those software applications.

The first question often is…

What do I need to do about the end of support?

… when the first questions should be:

What products are impacted by end of support?

What do these products do?

Do we currently run or use any of these products?

So let’s take a step back and answer those questions.

What products are impacted by end of support?

1. Windows Server 2008/R2 January 2020
2. Windows 7 January 2020
3. SQL Server 2008/R2 July 2019

What do these products do?

1. Windows Server 2008/R2 – is the foundational software used by most companies to manage their users, assign security permissions to users and groups, and support other software sitting on top of this foundation. The scope and impact is company-wide.
2. Windows 7 – is the operating system software used by end users on their individual desktops/laptops and support other software sitting on top of this foundation, for example, Outlook, Microsoft Office. The scope and impact is the end user.
3. SQL Server 2008/R2 – is the database software other software uses for database functionality, for example, Great Plains, industry specific software. The scope and impact is company-wide.

Do we currently run or use any of these products? To know if you are using any of the solutions impacted by end of support, you should rely on your technology department or provider to conduct an assessment of all the systems currently in use and provide a report showing the current versions and usage of those products. Once you have a report, whether you have 1 or 100 systems impacted, you should then use the information to develop a plan for addressing each one. Some systems may take months to address, so having a plan sooner than later will save management potential stress and sticker shock. WHAT TO EXPECT. Let’s assume you’ve had an assessment done and determine you have 4 servers running Windows Server 2008 R2 and 25 workstations/laptops running Windows 7 Professional. Developing a plan for addressing them should be tailored to your specific business, budget and system use. Workstations may be replaced quickly, where servers may take months.

Cost is not the only factor.

Using our example, a ‘refresh plan’ should be defined for every workstation running Windows 7 Professional. If the workstations are 4 years or older, it may make more fiscal sense to replace them with new machines running the latest Windows 10 operating system. If the machines are still acceptable from a performance specification standpoint, it may make sense to upgrade the machines to Windows 10 Pro from Windows 7 Professional. Aside from the costs related to these options, consideration should be given to how employees are using those machines and what potential improvements might be gained from a machine replacement versus upgrading only the software. To avoid a large capital expenditure (CAPEX) cost at the last minute in December, you may want to spread out the purchase of replacement machines over the next 5-6 months. A simple method is to take the number of machines, 25 in our example, and divide by the number of months remaining before you want them all replaced. It is now June, so assuming replacement needs to be completed by January 1, 2020, purchasing 4 machines a month July through November and 5 in December would have them all replaced by year end, spreading the cost over time.

Migrating servers from Windows Server 2008 R2 requires more analysis and planning because typically servers are running mission critical software applications for the business. It is not best practice to upgrade a Windows Server operating system as you typically would with a Windows end-user operating system and in most cases, it would be recommended to migrate to a new installation. Some standard questions to consider during planning include –

1. What business software is running on the server? Will that software run ‘as-is’ on a new version of Windows Server 2016 or will it require an upgrade as well?
2. Is business software running on Windows Server 2008 R2 that is NOT supported by later versions of Windows Server and will not run on later versions? Should the business software be replaced with software more current and supported? Should we continue to run the software on Windows Server 2008 R2 knowing the significant security risks?
3. What impact will downtime have on the business related to migrating servers?
4. Can they all be migrated during a single timeframe (likely a weekend) or does it need to be a phased approach?
5. Does the server hardware need to be replaced along with the Windows Server software? If so, what are the options now available that may not have been available 2-5 years ago?
6. Will our customers and vendors be impacted by any of these changes? What notices should be sent prior to the changes?

Don’t wait. Get help.

If all this seems overwhelming, you’re not alone. Many companies read the headlines and do nothing about it because it’s just too much to contemplate and is a major distraction to normal business duties. Because of the very real security risks, this is one of those times procrastination can really hurt the business exponentially more than the cost associated with addressing the issue.

You don’t have to do it alone. Fluid has been working all year and will continue to through the end of the year to do the heavy lifting for companies. From the assessment, planning, recommendations, obtaining necessary quotes, working with third-party vendors, and implementation, we try to do as much as possible to keep the business running. We will take on the tasks management and operational staff don’t have time to deal with. The additional benefit is knowing it will be done with technology proficiency and discipline many companies simply don’t have in-house.

If you do not know if ‘end of support’ will impact your company, you are at risk. At a minimum, knowing your exposure should be a top priority. Waiting until December may make the holiday season more stressful than it needs to be. If you need help, we’re here to do so.

You can reach Fluid at 866-802-9848 or via email at secure@fluiditservices.com