10 key warnings for your Windows 10 migration

5. Plan on a backlash

No matter what you do when you roll out a new version of Windows, you’re going to get backlash. Some of it is trivial, but a lot of it has to do with “muscle memory” and retraining. The initial step from Win7 to Win10 will draw howls of pain, frequently from your most experienced users (and staff!).

You can ease some training concerns by changing the way Win10 works, to align the Start menu more closely to the familiar Win7 Start menu. Two third-party tools draw a great deal of praise: Start10 and Classic Shell. They won’t silence your harshest internal critics, but either will help bridge the gap.

6. Licensing gets hairy

Windows 10 brings new twists and turns to the arcane art of Windows licensing. You are no doubt familiar with the old world: Enterprise (and Academic) Edition, Volume Licensing, Software Assurance. In the new world, you get to work with E3 (roughly analogous to Software Assurance), E5 (includes Advanced Threat Protection), and many variations on those themes. And then there’s Azure.

You can rent Win10 E3 and E5 with a Volume License from Microsoft, or from Cloud Solution Providers. In addition, you can rent the Win10 Secure Productive Enterprise E3 or E5 package, which includes Office 365 and Enterprise Mobility + Security. If you currently have a license for Win7 (or 8.1) and you jump to the Secure Productive Enterprise level, your older machines can be upgraded to Win10 free.

While your head’s spinning anyway, you can now rent E3 with Azure Active Directory and other cloud support, through the Windows 10 Enterprise E3 in CSP program for $7 per user per month. You can rent E5 in a similar fashion, but the Cloud Solution Providers set the price. Both let you run Win10 Enterprise on up to five devices per user, but the rules for managing those devices is complex.

Licensing is a minefield. Best to consult an expert.

7. Security is better in Win10, but you need people who can manage it

To many people the No. 1 reason — arguably the only reason — for moving to Windows 10 is its improved enterprise-level security. There’s a great deal of merit to that assertion. Microsoft always claims that its latest version of Windows is “the most secure ever.” With Win10, though, the defenses have certainly ratcheted up.

In no small part that’s because the nature of attacks has changed significantly over the past few years. In the not-so-good old days, the attackers were largely ad-hoc individuals or small groups, frequently with nothing greater than creating mayhem in mind. Nowadays, attacks run the gamut from ransomware to personal data mining on a massive scale. Attackers are frequently both well-versed and well-heeled.

Microsoft has a good high-level view of the problems and their Win10 solutions in “Mitigate threats by using Windows 10 security features.” As you read that article, keep in mind the caliber and commitment of individuals you’ll need to hire to make it work.