Gentoo or Slackware.

Although, technically Debian.. Because I had Debian 1.0 on CD, and had no idea what I was doing (no idea if that even came with Xfree86, if it did, I didn't know how to run it at the time)

People today have it easy since Xorg added auto configuration, PulseAudio was added and manufacturers started treating Linux as a Tier 1 OS.

I think Gentoo back in 2005. I left my laptop compiling OpenOffice while I went to class for the day. When I came home the laptop was off, so I had to start over. My roommate denied responsibility. The next day the same thing happened! It turns out I hadn't configured the fan correctly - or I guess at all - so the laptop had been overheating leading to emergency CPU halt.

But I've been using Linux since 2002. A lot of distros used to be a lot harder. But it's also hard for me to remember what the struggles were so long ago.

No doubt the hardest was the first one. I recall it was slackware with kernel 2.x around the late 90s. Having to recompile the kernel and configure manually the scan line freq for the monitor made it challenging. Ah yes, the man pages I printed them at work, that was all I had access to. No internet.

The first one I installed (doesn't matter its name) as it was the one forcing me to question all my decades long habits and to build new ones.

SLS Linux. I feel old.

First challenge: getting it.

It was about 25-30 3.5" floppy disks, but you had to download the disk images, and I downloaded them to my PC via a modem connected to the modem pool at the University where I worked. At the time, they had no limits on the use of the modem pool, so I was able to stay connected and just keep downloading until I had it all.

Then, you had to manually create the disk partitions and create the file systems on them. When that was all done correctly, you could run the install script.

I switched to Slackware when it came out. I also downloaded that to a SunOS box at work and used that to write the floppies.

It's more "annoying" than hard, but... Linux From Scratch. Having to mix and match every element (to see if they work) can be a very frustating experience.

Suicide Linux of course.

Linux from Scratch

Everything is built from scratch.

First, you need some kind of host Linux system, which then is used to compile and install everything to target environment.

It is quite a huge undertaking, needs lots of time and patience. Basic LFS book is around 280 pages, and it will just give Linux terminal - you will need to go Beyond Linux from Scratch to actually get desktop environment running.

I have installed it twice, as a learning experience.

https://www.linuxfromscratch.org/

Gentoo. I've gotten to stage 3 a few times, but somehow I cannot get past it (Be it a VM issue or a skill issue)

Probably trying to design and build my own custom distro. There's help like LFS but you still need to read an entire book and learn about a million important decisions to make. I scrapped the idea. It's just hard and then how am I even going to maintain it?

Slackware, back when the Linux kernel was still static and had to be configured and compiled each time an update came.

in the early 00's it was Mandrake. totally borked my HDD trying to install that and nuked my Windows XP partition in the process. just couldn't wrap my brain around it.

as for recently? Slackware. My Dad uses it but I just couldn't get it working correctly. More than likely it's simply because I did something wrong during install or setup post install. I've installed Gentoo a few times and I currently use NixOS and OpenBSD so I don't think i'm stupid, I just messed up Slackware.

Sort of in keeping with the people saying "the first one I installed", for me that was some 20 years ago with early Fedora and Ubuntu, I forget which order I tried them but it took multiple attempts over different hardware, any Linux was definitely more "difficult" back then, worse when combined with being a noob. I think some people don't know how easy they have it.

As for modern distros, it depends what you're trying to do; for example you might say something like Gentoo, but Gentoo has good documentation and is arguably "easy" for what it's specifically trying to be.

I've tried all the "main" ones over the years and the only one that's consistently defeated me is Slackware - somehow I could never work that one out.

I to this day have yet to get a successful Gentoo install. Virtual or bare metal and following walkthrough I always fail on compile. Before that though I always struggled with Slackware. The concept of Slackware is something I love, but I have always struggled with the setup and especially installing new packages and updating.

NixOS. A beautiful idea that had me fight it constantly. That was after daily driving Arch for 10+ years, so I was no newbie. It's one hell of a learning curve.

Exherbo's fresh on my mind, so it springs to mind first.

But I doubt it's the hardest.

Could perceive GuixSD as harder (~ I swear, even as a bedrocklinux user (with it's longer file paths and other complexities and extra concepts to grok), I'll never get used to the GuixSD/NixOS confounding noisy style of file paths, with those fat hashes in the middle).

And if what's harder, is changes to the file system, different to the conventional norms, then maybe GoboLinux is harder. Nice as the idea is, I never managed to really daily drive Gobo for any meaningful duration. I at least managed to stick with GuixSD for months.

Distros like CRUX, and also KISS and Carbs, spring to mind. It's a different kind of hard again.

But for sure not the hardest. There will be some even more obscure distro I'm forgetting, because it was too hard.

Do distros that just failed to install for some reason, count as harder, in my experience, since they were just a hard wall blocking getting further? Because some distros I did not even figure out how to download, so they'd be even harder?

Ah, but, the question is indeed "tried", not "used".

I tried NixOS, then gave up when I realised how much had to be learned for its package management language that would not be a transferable skill learned (~ and it was then I decided to run GuixSD, and learn guile, lol, I know no guile from a few months in GuixSD years ago). Maybe that's more a case of tried to try.

And LFS's another "tried to try" (several times even). But always giving up before can really say "tried".

Joborun, might be one of the more obscure examples, that had some hardness to it, that I'd actually tried to ride along with... but that was more a (for want of a different description) a penance amidst familiar comforts. [Edit: and joborun kinda invited [/insisted] more attentiveness, so that, in a way, made it easier to be attentive enough to use something arch-based more properly (e.g. not using AUR blindly)]

I dabbled at making my own (~ respin + scripts + things + grander ambitions). That was pretty hard. Though, the hardest part, was the cat herding community aspect. Not running it.

I tried doing hardened gentoo... that hardest?

I've done decibel linux many times since around 2008 (though it was called gentoo studio back then iirc). If one were to partake of decibel without first learning at least a little gentoo... that's hard. And I only did my first stage3 gentoo install in 2010. [Edit: Oh, and last time I checked, the site was down, and couldn't get the stages from the wayback machine... so that's even harder to try decibellinux now. ~ hoping the guy's okay. ~ which reminds, XeroLinux, another distro I've tried, that's hard in a different way, emotionally, concerned for the developers wellbeing.]

And so I don't think I'm going to include bedrock as a candidate for the hardest... because by the time one arrives at a need for bedrock, one is already comfortably familiar with (likely) many distros, and the amount learned already is still more than the sizeable amount of learning new things required for bedrock, and so, like other distros [though, confoundingly, every distro example coming to mind are also each in their own way exceptions to this rule], that just take a bit of time diligently attentively learning and following the documentation, it's not hard, especially from the likely entry point.

So perhaps I just never really pushed harder... if one were to jump sooner to something harder... then it'd be harder. But the things that would seem harder to the novice, are not hard once you arrive there with the knowledge that brought you there.

Perhaps the hardest, might have been the first, simply because as a windows refugee, it was like going from 0 to 1, the initial infinite step change, where everything after that is easier.

... So wait, am I going to say SuSe is the hardest distro I've tried? lol.

Yeah. Final answer. Suse is the hardest distro I've tried. Simply because it was my first.

Honestly I have never been much for my home machine being overly complicated. Yeah back in the day I made my own rig but at home I mostly want to use it and not support it. I used linux at work though as far back as the early aughts and nothing today I think is as complicated as that. So I simply have not used a hard one in my day to day. Pretty much went puppy to zorin (ubuntu) to bazzite.

I don't remember which one it was but it was back in like 95 and it was the supposedly user friendly one because it had a terminal menu system for installation that only required figuring out every chipset in your beige box yourself and picking out drivers for manual compilation of the kernel and hope it was enough but alas something else didn't still work and when everything supposedly did there were obscure crashes that had no hits on neither Altavista nor usenet and you were called a lamer for not knowing how to fix whatever in C/Cpp yourself.

Turbolinux 6, which was the first Linux distro I tried and which I never successfully installed because I was a high-school kid and had no idea what I was doing.

(Why Turbolinux and not some other distro? Because it's the one I found a physical, boxed copy of. I can't remember if I bought it at a store or somebody gave it to me at a Ham Fest -- more likely the latter -- but I definitely didn't download it.)