In the decades since I started using Linux, I’ve experienced just about every distribution ever created, some of which were user-friendly and some of which were not. In some cases, I was determined to use them just for the bragging rights that I’d installed and used one of the most challenging operating systems on the planet. Other times, I just needed something to work out of the box.

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If you’re new to Linux, you’ve probably come across lists of distributions you should try first, like Ubuntu, Linux Mint, elementary OS, and others. What you might not have read, however, is a list of distributions you should avoid until you’ve mastered the command line and aren’t afraid to do a lot of things manually.

But what are those distributions? Behold! The list.

1. Linux From Scratch

Linux From Scratch (LFS) is the single hardest take on Linux you’ll find because it’s not a distribution per se. Instead, LFS is a set of instructions for building your own distribution from the ground up. Sounds hard, right? It is. One of the reasons LFS exists (other than creating cool Linux distributions) is to help people learn three important deep-dive concepts:

• Compiling the kernel
• Installing base system software
• Configuring and installing hardware drivers

When you have a solid understanding of those three concepts, the sky’s the limit with what you can do on Linux. On top of that, when you finish with LFS, you’ll have a custom Linux distribution that you can either use yourself or distribute to the world.

2. Gentoo

Gentoo Linux is the most challenging of all the Linux distributions available. The reason Gentoo is so challenging is that you have to compile everything from source — from the OS to the apps. If you’ve ever compiled an app from source, you know how challenging dependency spirals can be. You attempt to compile App X, only to find out it depends on App Y, but App Y depends on App Z — and so on. I’ve spent hours trying to solve dependency issues, and it’s not fun. Imagine doing that for every single app on a system. 

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Until you feel like you’ve mastered the fundamentals of Linux, don’t even think about Gentoo.

3. Arch Linux

Arch Linux gets the nod because the installation process isn’t nearly as user-friendly as other distributions. Unlike some of the forks of Arch (such as Manjaro), there is no GUI OS installer, which means it’s all handled from the command line. That is not to say the installation is impossible for newcomers. The developers have simplified the process somewhat, thanks to the archinstall command. Instead of having to first create an installation file, you can run the command and answer the questions. 

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Even with archinstall available, I wouldn’t recommend Arch to anyone new to Linux.

4. Slackware

Slackware is one of the oldest Linux distributions on the market. While Slackware is also one of the most stable operating systems on the planet, it lacks the standard fare of user-friendly tools and automated updates. Additionally, Slackware uses the slackpkg package manager, which requires cleaning up older packages before installing new ones. The most challenging aspect of Slackware, however, is that it offers no automated dependency resolution (similar to Gentoo). This can cause problems for new users who are accustomed to using an App Store for installing applications. 

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Using Slackware involves reading a lot of man pages (and other documentation) for things that other distributions do automatically.

5. NixOS

If you don’t mind configuring every single aspect of your system, NixOS is a good option. Beyond that, NixOS uses a unique package manager that requires you to think about how you want every part of your system to behave (such as the UI, network, and security). Another challenging aspect of NixOS is installing non-free software. Fortunately, NixOS has created the search.nixos.org site that allows you to search for an app and view instructions on how that app is installed. But for those unfree apps, you have to set nixpkgs.config.allowUnfree = true in /etc/nixos/configuration.nix. 

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With a little effort, you can get NixOS up and running, but it won’t be a walk in the park.

6. Void Linux

Void Linux isn’t based on another distribution, as it was created from scratch. Like many of the distributions on this list, Void uses a unique package manager (xbps), which is similar to Arch’s pacman. To install an application, you would use something like sudo xbps-install -S git. One interesting feature of xbps is that it also allows you to install from source. To do that, you would clone a repository (or download the source) and then build/install the package with the following commands:

./xbps-src pkg PACKAGE
sudo ./xbps-src install PACKAGE

Where PACKAGE is the name of the package to install. Void Linux does include Flatpak support, so you do get a bit of user-friendliness there (although without a handy GUI).

Also: I’m a Linux power user, and this distro made me rethink what an operating system can be

Another issue with Void Linux is that it doesn’t use systemd as its system/service manager. For some, that’s actually a bonus, but those who are new to Linux will find that much of the information on the web is about systemd. Finding documentation about OpenRC isn’t nearly as simple (nor is that init system easy to use).

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