Migration from legacy Windows Operating Systems to Windows 10 Exceeds Project Goals—and Teaches Some Valuable Lessons

by: VMware Consulting Architect, AMER EUC Brooks Peppin

The enterprise community is quickly embracing Windows 10. Shortly after Windows 10 launched, VMware started migrating  legacy Windows systems (7 and 8.1) for both on-site and remote employees as quickly as possible. As with any major transition of this nature, there were numerous challenges and potential roadblocks including how to convert users to the Unified Extensible Firmware Interface (UEFI), where to store user (profile) data, and how to seamlessly migrate settings, files and applications—all while maintaining a consistent experience without any intrusions.

These key metrics determined the success of the project:

  • Minimal disruption to the business and our colleagues
  • All user settings/files were both fully intact and 100% accessible as before
  • The entire migration was zero-touch from an employee perspective (no user involvement needed)
  • Each system moved from legacy BIOS to UEFI mode
  • Minimal data loss or hardware failur       

The keys to success

Achieving project goals and overcoming the various challenges required several factors be in place:

A highly automated, in-place upgrade sequence enabled machine migration within two hours, significantly reducing the drain on IT resources. All user data and settings were maintained, with no interruption in operation regardless of location. The UEFI conversion ensured advanced security features were built-in from the start. It also removed the need for a second touch in the future.

Centralized logging and issue tracking allowed for faster problem resolution. Wiki pages and support documents with common errors and their resolutions were created, and all logs are sent to the central server for better visibility into overall system health.

An executive dashboard for progress tracking offered IT leadership clear visibility into project milestones and incremental accomplishments. Progress was monitored by location and region, encouraging healthy competition.

Workspace ONE powered by AirWatch technology enabled VMware IT’s co-management strategy with the System Center Configuration Manager (SCCM). AirWatch is now used for priority payloads such as wireless network configuration, Windows Updates, securing devices with BitLocker, as well as delivering software with the new Workspace One application. VMware IT is accelerating the move to Modern Management for Windows 10 by adding new payloads such as BIOS management and software distribution with peer-to-peer support for these devices.

Replacement hardware was deployed to those systems that simply could not take Windows 10 or were not compatible with UEFI and TPM. Additionally, in order to minimize end-user downtime, loaner and lightly used equipment was utilized for those inevitable hardware failures.

Did it work?

The transition began in July 2016. By the end of 2017, 99% of Windows 10 compatible VWware machines had been successfully migrated. All key objectives were achieved and user disruption was either minimal or nonexistent depending on location.

What did we learn?

  1. Laptop hardware failure happens as bad NICS, SSDs, screens, and motherboards were discovered. Plan to have break/fix hardware replacement devices on hand.
  2. Leverage Windows 10 migration as the spring clean-up opportunity for your apps and policies and making the transition to Modern Management.
  3. All business apps must be tested for Windows 10 compatibility prior to any migration.
  4. Partner with your colleagues to determine which groups should be migrated first. Leave the most complex groups for last.
  5. Cloud backup solutions are an ideal complement and ‘failsafe’ for user data.
  6. UEFI conversion does not allow reversion to a prior OS when using the in-place upgrade method.
  7. Great communication and ‘public relations’ are key to ensuring every employee is on board. This includes possibly offering giveaways.

What’s next?

  1. Start now and keep progress going. The Windows 7 and 8.1 end of life dates are approaching rapidly.
  2. Have a look at some other great, best practices.
  3. Leverage the free Windows 10 migration tool from VMware to help you analyze your current environment.
  4. Want a more detailed blueprint? Follow this guide.

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