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June 10, 2019 general

Windows 7 Dies in Six Months. Are You Ready?

Windows 7 end of life countdown Computer upgrade and operating system migration

We first warned about Windows 7 end of life in July 2018. At 18 months out, it felt like plenty of time. Now we're at six months. January 14, 2020 is the hard deadline. After that: no more security patches, no more updates, no more support.

If you still have Windows 7 machines in your practice, this is your final planning window.

The Current Situation

As of June 2019, Windows 7 still runs on roughly 35% of business PCs. Despite 18 months of warnings from Microsoft (and from us), migration has been slow. Common reasons we hear:

  • "Our PMS only certifies on Windows 7" (check again, most have certified Windows 10)
  • "The machines work fine" (they won't be fine without security patches)
  • "We'll do it next quarter" (you're running out of quarters)
  • "It's too expensive" (it's less expensive than a ransomware attack on an unpatched OS)

Your Six-Month Checklist

June: Inventory and Verify

  • Count your Windows 7 machines (you may have more than you think)
  • Confirm Windows 10 compatibility with your PMS vendor
  • Confirm Windows 10 compatibility with imaging software and peripherals
  • Identify machines that can be upgraded vs. need replacement

July-August: Budget and Order

  • Budget for Windows 10 licenses ($200/machine for Pro) and any new hardware
  • Order replacement machines for hardware that's too old (generally pre-2012)
  • Schedule the migration with your IT provider

September-October: Pilot and Train

  • Upgrade one machine first and test all workflows
  • Train staff on Windows 10 differences (minimal but worth 15 minutes)
  • Document any compatibility issues and resolve them

November-December: Full Rollout

  • Upgrade remaining machines in phases (2-3 per week)
  • Verify all machines are receiving Windows 10 updates
  • Retire or repurpose Windows 7 machines

January 2020: Zero Windows 7

  • Confirm no Windows 7 machines remain in production
  • Update your IT documentation
  • Celebrate with the knowledge that WannaCry 2.0 can't touch you

What Happens If You Don't

After January 14, 2020:

  • Every new vulnerability discovered in Windows 7 will remain permanently exploitable
  • Attackers actively target end-of-life operating systems
  • Your cyber insurance may not cover incidents on unsupported systems
  • HIPAA auditors will flag unsupported OS as a compliance violation
  • PMS and software vendors will stop supporting Windows 7 configurations

Six months. No excuses. Get it done.