Installing Debian Linux 2.1 From 1999 Was A Painful Experience ...

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Published 2021-01-16
In the first video of 2021, I decided looking at a sealed box of Debian Linux 2.1 from 1999 that I found on eBay would be a fun way to set the tone for the new year. Sponsored by VA Linux, this box proudly claims that it's the last Linux you'll ever have to buy, trouts up the advantages of apt-get, and that you would never have to buy software again.

Included in the box was a demo disk of Myth II from Loki Games, offers of StarOffice, and much more, but what I would find in practice is that, at best, most of what was offered was optimistic at best, and downright deceptive at worst from VA Linux. Compounding the issue, VA muddled this release of Debian by only including one of a two CD set, but this glosses over a large number of issues in trying to use Linux in this era, as well as the oddities of Debian in specific.

As compared to almost any other distribution, Debian had a reputation of being somewhat difficult to install (although its admittedly better than Slackware), but what would surprise me the most is that Debian's overall user experience was far less than that of Softlanding Linux System from five years prior.

This doesn't help that Debian is overly complicated and it would take many years of effort (primarily from Ubuntu) that would help smooth out many of the rough end of this product. While this video only goes into the ins and outs of installation, it would show what a miserable experience a user would have, and some of the major mistakes made by VA Linux. It would also show that while Debian has become a cornerstone of many Linux distributions today, it would also have a difficult start and genesis.

Interesting Timestamps:
00:00 - Intro
00:57 - The Golden Age of Big Boxed Linux
03:10 - Cutting the Shrink-wrap
05:00 - Dual-booting Discussion, FIPS, and PartitionMagic
06:10 - Starting Installation
07:12 - Disk Partitioning
08:30 - Finding the CD-ROM
09:30 - Second-Stage Installer, tasksel, and dselect
12:00 - Trying to Configure Debian Properly ...
13:50 - Difficulty with gpm ...
15:08 - Debian's origins
16:33 - On The Topic of Dial-Up Networking ...
18:30 - The Single CD Problem
19:20 - Post-Installation Problems
20:05 - Deceptive Packaging from VA Linux/Conclusions
21:50 - Signoff and Thanks
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Music is from www.epidemicsound.com/, with the following tracks used in order:
- Circular Thought - Ethan Sloan
- West of the Soul - River Foxcroft
- Without Purpose - Jon
- Rise of the Velcro - Gabriel Lewis
- Deviation In Time - Johannes Bornlof
- Infernal Machine - Bonnie Grace
- Maze Heist - Max Anson
- Person of Interest - Dream Cave
- At Evenfall - Howard Harper-Barnes
- In the Aftermath - Michael Rothery
- Night Thoughts - Max Anson
- Chasing the Truth - Dream Cave

This video is a corrected upload since the original had broken audio issues.

All Comments (21)
  • @zigginzag584
    this is probably why Linus says he can't figure out Debian 1999 was the last time he tried.
  • @Thanatos2996
    Linus's quote about not using Debian because it was difficult to install last time he tried is making a whole lot more sense now.
  • @RexTorres
    So, you're basically buying a book with a free CD...
  • @thpeti
    My first Linux was a Debian 2.2 "potato" when I was around 17. My middle school IT teacher copied it on 3 CD's for me. I loved it, I could find almost everything in the dselect utility, I've even installed it on a 486 which I built from junk computer parts, and made a router to share the 56k modem with my brother. In those times, there was a free dial-up provider in Hungary, but with limited slots available. It was free between 18:00 and 6:00, so i made a crontab and an automated wvdial script to get the slot every night. That machine had a Digital DEC203 (if I remember) 10mbps ISA network card and 4 MB of RAM, booted from a 120MB hard drive. My main PC was a Celeron 333 MHz with 64MB ram, running Windows NT 4.0 / Debian. I used this distro for copying DRM protected audio CD's for my friends. cdrdao made a "copy-protected-copy" of audio discs with "cactus data shield" or similar protection...
  • @garyburke6156
    oh my god I feel so vindicated, decades later. 22 years ago I got this exact box and tried, struggling, for hours, to install debian. i got it working eventually because i happened to be friends with one of Debian's core developers, who provided me excellent and thorough support, but it was still a nightmare getting slink up and running. And I thought it was because I was a dumbass. Its shit like this that made me embark on a career in UX design. I may well be a dumbass, but thats not why i had so much trouble with this debian install back in the days of pentiums and giant CRT monitors. great video.
  • @ehs03y3ol
    I really appreciate how really well is now all documented. Even Gentoo seems much better end-user experiencie than this :/
  • @kostis2849
    Oh damn. I avoided Debian like the plague back in the day, now I remember why. That hurt....
  • @aguy2093
    Damn am I grateful I was born in a time where GNU/Linux is easy.
  • @Yezu666
    It's nuts how much Linux has improved. I started with Linux around 2004 and it was tricky at times, but manageable. In the 90s you had to be hardcore to use it. In the early 2000s you had to be an enthusiast, Linux was good for every day use, but was still playing catch up to Windows. Now? I'm confident to say that using a distro like Fedora, Ubuntu etc. is a much easier, smoother and pleasant experience than using any version of Windows.
  • Considering how easy Linux is these days this is a complete nightmare lol
  • @shellgecko
    Now I understand why linus torvalds never used debian
  • @commentarysheep
    It's just simply a miracle that after 22 years in the oven, Debian has gone from a frustrating install experience that involves a lot of know-how about how your computer works and typing in alien-sounding commands to Debian just ending up using Calamares in Debian 11 and providing a "click Next-Next-Next-Install and you're done" install experience. I have to say I got into Linux at the right time.
  • @jonshouse1
    I am showing my age here, but I remember install Xenix on a 386 with an MFM HDD, this made the Debian partitioner seem good. To install Xenix (first versions) you needed to calculate the partition heads/cylinders/sectors with a calculator, if you got it even slightly wrong the system would install (taking about 5 hours and 35 floppy disks) then round about the second reboot it would corrupt its hard disk and crash, needing to be installed again from scratch. Over a period of a week I did this 4 or 5 times before I got a working machine.
  • @juancriolivares
    I started to use Debian around the year 2000. I remember it was super easy to install. Once, I left a Debian installation CD inserted and the monitor disconnected. Someone tried to make the computer work by rebooting and pressing enter a lot of times... Big was my surprise when I discovered she was able to re install Debian by just pressing enter a bunch of times :)
  • @sugaryhull9688
    I've used Debian since version 8 and it's nice to see how far it has come since then. Never had any issues with it that weren't self-inflicted
  • @Psy500
    Mandrake 7 come out shortly after and was my first experience installing Linux; I'm so glad I didn't have to put up with this.
  • When I was a kid in 97-99 somewhere, one of my computer magazines included a Slackware CD. The installation process was identical to this. The questions were extremely hard. Especially since I had never seen Linux before. I remember doing like 5 retries until I finally had a booting graphical system. I noped at how ugly the desktop was. And went back to Windows...
  • @RussellFlowers
    I wasn't big into this scene at this time, but I imagine this is why Linux User Groups were so popular - people helping each other.