What does the upcoming end of life for Windows 7 mean to me?

As many of you may already know, support for Windows 7 and Windows Server 2008 officially ends on 14 January 2020. It may seem like a long way off but now is the time to begin planning your migration. In the interest of brevity, I’ve tried to be short and to the point below with some quick ‘what does this mean’ and ‘what do I do’ points but, if you have any questions or if you’d like for Cyber Tech Cafe to help with your migration, definitely let us know.

What does this mean?

Microsoft works with it’s internal staff as well as it’s Bug Bounty program to find vulnerabilities (bugs and other problems) in it’s products. They then write updates (fixes) and release updates every month that users can install so that cyber-criminals and miscreants can’t use those bugs to do evil (steal information, destroy information, etc.). As of 14 January 2020, even if new bugs are discovered, no updates will be released. Users still using Windows 7 or Windows Server 2008, will be left vulnerable to any new attacks.

In addition to the security implications of running an unsupported operating system, there will also likely be problems as third party vendors (productivity applications, security applications [antivirus, etc.] and others) stop supporting the out-of-date operating system.

What do I need to do?

Inventory. If you don’t already have one, inventory your current network to find out how many Windows 7 and Windows Server 2008 systems you have. It’s also a good idea to use this time to make sure that there are no older systems (Windows XP, Windows 2000, Windows Server 2003, etc.) still running. It’s worth noting that an inventory of authorized and unauthorized devices in your environment is the very first thing listed in the CIS top 20 critical security controls.

Do you have any software or hardware that do not work with Windows 10 or Server 2019? Armed with the information from your inventory, reach out to other hardware and software providers to confirm that their products (and the version of the products that you are using) support and are supported by the updated version of Windows. An example here would be Dexis dental sensors; There are a number of these that are still 32-bit only that cannot be used in a 64-bit environment. These are a couple of thousand dollars per so, in even a small dental office with a few of these installed, that will impact the budget significantly.

Plan. Are you going to upgrade or replace? You may be able to upgrade the Operating System from Windows 7 to Windows 10 without replacing the hardware. The actual cost difference between the two is often negligible and it’s more cost effective long-term to simply replace the older computer but, if short term budget is the primary concern, this may be an option. I would not recommend installing Windows Server 2019 on the hardware that’s currently running Windows Server 2008.

Schedule. This needs to be done no later than 14 January 2020. We are recommending to our clients that they have the project completed by no later than 1 June 2019. This will provide sufficient wiggle room if something goes wrong (hmmm, I guess that was the 32-bit only version of that sensor, now what). It will also get them ahead of the last minute buyers and the inventory shortages that will likely result from everyone trying to do this in Q3 and Q4 of this year. Including a period of time (a week to a month, depending on your organization and your users) for a test group to use the upgraded system(s) and make sure that there are no surprises may also be helpful.

Execute. Now that you know what you have, what you need and when you’re going to do it, execute.

Clean up. Any of the computers that were replaced will have your data on them. Before you get rid of them (recycling or donating them), make certain that you’ve securely erased any data that’s on them.

If you have any questions or would like assistance with any part of the process (from simply bouncing questions off of us to outsourcing the entire migration to us), let us know. We’d love the opportunity to earn your business.

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