Windows to Linux in the Enterprise: building the “sysadmin bundle”

Migrating from Windows to Linux in a company is not the same thing as what a home user does on a personal laptop.

At home, you install a Linux distro, you are the admin, you have no directory services, no fleet to manage, no policies to enforce, no compliance constraints, and most of your work happens in a browser anyway.

In an enterprise, you don’t throw an existing ecosystem in the trash overnight. You need a smooth transition. That means interoperable protocols and a progressive migration path.

No “big bang”

The “big bang” method almost never works. It’s the best way to break something critical and lose trust internally. A realistic migration is a coexistence period where Windows and Linux desktops run side-by-side, and services keep working for both.

That coexistence is only possible if what you deploy is based on standards and interoperable protocols (Linux ↔ Windows), so everything continues to function even when you must keep some Windows machines (because a business application only runs there).

Microsoft is (too) well integrated

It’s also important to admit something: Microsoft is extremely well integrated.

Windows is a “turnkey” desktop OS for enterprises, with a lot of sysadmin building blocks designed to work together out of the box: identity, policies, device management patterns, encryption workflows, certificate enrollment, remote access, and so on.

On Linux, that “sysadmin bundle” exists, but it is not delivered as one single coherent package. It’s something you have to assemble: pick the bricks, make them work together, and make the result manageable at scale.

That is the real topic of this article.

Not about servers

This article is not about the server side.

Today, building a server environment entirely on Linux is often the easiest part. The real challenge is the desktop side: managing endpoints, users, authentication, security controls, enterprise workflows, and long-term operations.

Not about choosing a distro or a desktop

I’m also not focusing on distro choice or desktop environment selection. That debate is mostly sterile and doesn’t solve the core problem.

The hard part is not “GNOME vs KDE” or “distro X vs distro Y”.

The hard part is: how do we replace the Windows enterprise admin ecosystem with something solid on Linux, while staying interoperable during the transition?

A growing list of enterprise “sysadmin” use-cases

I started listing the main “sysadmin-side” use-cases that need an interoperable migration path on GitHub. The list is a work in progress:

• some use-cases already have solutions (built or ready to use),
• some have partial solutions (still being built),
• and some still don’t have a clear equivalent.

Repository here:
https://github.com/sfonteneau/windows-to-linux

Interoperability: protocols first

Interoperability is relative.

Some things can’t be “interoperable by design” because they are vendor-specific concepts. A good example is AppLocker: it’s not a protocol, it’s a Windows feature. In that case, the goal is to find an equivalent on Linux.

But the protocols and integration points should remain interoperable wherever possible (identity, authentication, file sharing, certificate workflows, remote access…), because that’s what makes a progressive migration possible and avoids breaking mixed environments.

What’s next

Soon I’ll publish a similar “Windows → Linux” list for the server side — which should be simpler.

For now, the focus is the desktop migration and the missing “bundle” that needs to be built for Linux in enterprise environments.