I’ve been on several sides of this. As a sysadmin supporting a Windows dominated environment integrating Linux, as a user who wants to use Linux in a Windows dominated environment and in security trying to secure an environment with both Windows and Linux. In short, it depends on the use case, environment and the users’ tolerance for problems.

The first question which will come up is, “why?”. If you don’t have a good business use case, you should expect to be basically told to go get fucked. I realize that this seems like IT sticking their head in the sand, and it kinda is. But, also realize that you are asking them to take on extra work for nothing more than your own self edification. I have yet to meet an IT department which is so overflowing with time and resources that they want to take on new work which isn’t required. Even with the most basic use cases for Linux, IT is going to need to have resources dedicated to support, maintenance and oversight. Things like asset management, patching and license management don’t go away on Linux systems. Sure, the OS may not have a license to worry about (unless it’s RHEL or Ubuntu Pro), but there may be other software installed which is licenses and that license may be a different SKU on Linux. Then there are issues with ensuring IdM works on that flavor of Linux and supporting it when it breaks.

Along side that “why” question, be ready to answer the “why not” questions. Why not a Windows based alternative? Why not Cygwin/WSL? Why not a Linux based server that you SSH into from your main Windows desktop? Especially with a lot of workloads moving to the cloud, I’ve seen the mainframe model start to return, just with Linux instead of Unix/AIX this time. This sort of thing centralizes a lot of the IT headaches into a single host (or handful) which can much more easily be centrally managed. And that’s a theme to keep in mind, IT departments love centralized management. This is one of those places where Linux kinda lags Windows. Centralized management does work on Linux. It’s one of the reasons RHEL is all over the place, Satellite is like crack for IT departments dealing with Linux. But, a lot of centralized management looks like a folder full of Ansible scripts. With proper code management, it can work quite well. Keep in mind that many folks in IT are not coders and for a handful of Linux systems, dedicated resources which can handle that may not be in the budget (in the end, everything is about money).

Ok, so you have your “why” and are ready for “why not”. Let’s talk about the security stack. No, just because it’s Linux doesn’t mean you can ignore security. I’ve personally worked cases where Linux boxes got popped. And from the user side, things like ClickFix attacks are starting to crop up targeting Linux desktops. So, does your company’s software stack support Linux? This has, thankfully, started to be more common. Go back a decade and the answer was almost certainly, “no”. Partly because Linux wasn’t that common and partly because idiots believed Linux was fully secure by design. Anyone who believes that today shouldn’t be allowed to work on anything more advanced than an Etch-a-Sketch. With the dominance of Linux in the cloud, attackers are targeting Linux and your system will need to be ready for it. If your company’s security stack doesn’t support Linux, and/or your security department doesn’t have the expertise to monitor and respond to issues on Linux systems, you might find them resistant. Thankfully, that whole “Linux dominating the cloud” thing has started pushing security teams towards supporting Linux. And more advanced security teams often utilize Linux themselves in some capacity. So, that could ease your path a bit.

The final bit might be your tolerance for pain. If you’re out there on the bleeding edge, trying to be the first Linux system in an all Windows environment, expect things to break. No matter how well planned the rollout, the fact that the IT department hasn’t done this before means that they are going to miss stuff. It happens. If your system becomes a common source of trouble tickets, IT leadership may try to pull the plug. If you turn out to be a high maintenance user, you might find IT slow to respond and unwilling or unable to help with things aren’t working quite right. Some level of self-help and patience with a help desk which doesn’t have Linux expertise are going to be necessary. You really don’t want to become the phone number which pops up on the Help Desk queue and all the analysts scramble to avoid taking the call.

To conclude this long ramble. Linux systems in a Windows dominated environment is getting easier. That “the cloud” basically runs on Linux has gone a long way into getting Linux integrated into Windows environments. Microsoft has been forced to make their tools actually work with Linux, rather than the abomination which was setting up POSIX uids in a Windows 2000/2003 Active Directory domain. But, a lot of IT departments will still want to treat Linux as a server OS and not a desktop OS. MS Office, Teams and the rest of their communications and collaboration software still treats Linux as a pariah. Integrating and supporting Linux alternatives means budget and resources which aren’t dedicated to the core business. And that’s really what IT is going to care about.