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Romancing the Thinkpad 365

Two Morons and a Compact Flash Card

Spring 2022

Our Premise

Recently, a friend of mine decided to get into DOS VGA demo coding in C. While DOSBox is a great piece of software, nothing really beats The Real Thing when it comes to testing, running and even developing your demos. As luck would have it, another friend recently and very generously gave me a working IBM Thinkpad 365 laptop from 1997. It's a fully specced out technical marvel with a 75 MHz Pentium CPU, 40 megs of RAM, an 850 meg HDD, an internal CD-ROM and a surprisingly decent 800x600 screen. Along with it, I was also given a PCMCIA network card.

The top lid of a Thinkpad 365 onto which a sticker reading Amusing Canines has been applied
Correctly branding your hardware is key to making it run successfully.

The internal 850 meg hard drive had already been installed with FreeDOS, but the installation was sort of broken and it wasn't possible to start any of the drivers in order to install new software from the PCMCIA card slot or the CD-ROM. The external floppy that originally came with the machine was long lost. With no other machine handy that we could connect to the internal 2.5" IDE hard drive in the laptop, what to do?

Compact Flash! Ah-haah! Saviour of the universe!

I can navigate my way around a DOS machine in a pinch, but I've never actually owned one: my retro computing experience lies mostly in the field of Amiga. As luck would have it, though, the Amiga 1200 and 600, the two models I mostly use, both have internal 2.5" IDE interfaces and Compact Flash cards are basically IDE devices, which means that a simple adapter and some tweaking with AmigaOS' HDToolBox is all that's needed to format and partition them as hard drives. Would the same work in an old laptop as well? The short answer is yes, it works perfectly fine - but that doesn't mean two halfwits working together aren't going to first have to become Kings of the Impossible and complicate something very simple.

A Timeline of Cluelessness

1630 hours

Friend arrives. We immediately start by generally checking the laptop out and then begin downloading a FreeDOS hard drive image prepared in advance. It's swiftly written to a Compact Flash card using dd and a USB-to-CF adapter on my Linux box.

An opened IBM Thinkpad 365 surrounded by various tools and hardware paraphernalia
An open Thinkpad 365 and a lot of Very Useful Computer-type Stuff.

1650 hours

Opening the laptop up and performing hardware maintenance is super simple - a hallmark of IBM Thinkpads that still make newer models popular among hackers and open source aficionados. In the case of the 365, it's as simple as pulling two little plastic knobs and lifting the keyboard up. The hard drive is mounted directly on the motherboard, where the hard drive's male pin connectors slides onto a female connector instead of the more common variant with a female/female lead between the HDD's and motherboard's male pin connectors.

We replaced the old mechanical hard drive with our new and fancy CF card, closed everything up, congratulated ourselves on a job well done and proceeded to power on the computer.

Naturally, nothing happened. We swiftly rebooted and entered the BIOS - and what a wonderful BIOS it is! Unlike many machines contemporary to the 365, IBM crafted a fully graphical user interface which supports the trackpoint built into the computer. They even made a different mouse pointer for each of the settings screens - on the main screen, it takes the form of a duck in flight which flaps its wings when the pointer is moved. This alone is, in my opinion, a good reason to get your hands on one of these machines if you have the opportunity.

A photo of an error message in the IBM BIOS config.
Ahh yes, the old FRU 6010 is acting up again.

After a bit of figuring we realized that the hard drive had been mounted upside-down and simply flipping the IDE adapter over should do the trick. So we did. We also unanimously concluded that this slight oversight on our part wasn't due to us both being intellectual cul-de-sacs but rather because the designers of the Thinkpad 365 were the worst hardware engineers in the history of hardware, ever.

A CF card in a CF to IDE converter mounted on the Thinkad motherboard - facing the wrong way
A compact flash card facing the wrong way on a Thinkpad 365 IDE connector.

Naturally, nothing happened: we were just presented with a handful of dots on the screen and nothing more. Not even a FRU 6010 hint this time - or any other sort of error message.

Was it in fact dd that was the problem here? Was this, the most dangerous and useful of programs, really a steaming pile of crap and possibly the worst piece of software produced since OS/360? We at least knew it couldn't possibly be us that were at fault - after all, we are both experienced computer gurus and know exactly how to operate any kind of software and hardware through our innate geek powers.

No matter. Time to fire up gnome-disks and put our faith in The Magic Of The GUI™!

1710 hours

Turns out that gnome-disks is the worst program written since, like, Burroughs MCP, because after re-writing the CF card with it, the Thinkpad once again presented the same dastardly sequence of dots and then nothing more. Maybe writing the disk image to the CF card somehow cocks up (a technical term) the MBR? If only we had some kind of bootable install media with FreeDOS (or, really, anything else) on it that would allow us to examine the CF card while it's actually mounted in the Thinkpad, we could find out! The laptop has a CD drive, but who even as a CD burner lying around these days?

1715 hours

Well, not to brag or anything, but who's got two thumbs and is a legendary retrocomputing wizard in possession of unexpectedly useful hardware? You guessed it! Turns out my old (well, ten years anyway) laptop sports a bona fide burner! And there's an amazing program called Brasero (I guess "Manssiere" was already taken) that'll actually burn CD:s with it! Except... who even has CD-R discs lying around these days?

1730 hours

Nerds can move fast when they have to, and by now we were already on the freeway, heading for the nearest store still stocking CD-R discs. It was a beautiful spring evening with a glowing sun setting in a sea ablaze with reflections. A perfect time to drive at top speed towards a temple of mammon so that we could return indoors and fart around with outmoded computer hardware as soon as possible.

1750 hours (10 minutes before closing time)

Breathing heavily, hearts pounding and with the taste of adrenaline in our mouths, we casually strolled into the electronics shop and asked the pimply-faced clerk for a some CD-R discs. "And get us the top shelf product, buster. Not the off-brand junk you kids use to burn your illegal DivX rips and low-bitrate MP3 collections!" Our brazen demand was met with a look of shock and awe: clearly, we were people who knew our stuff and wouldn't take no for an answer. That's just how you have to deal with retail workers - otherwise the bastards will short change you and laugh all the way to the bank. Our strategy of ruthlessness and condescension worked: we walked away with 25 (count 'em!) sweet, shining Verbatim discs neatly stacked in a spindle.

An in-action shot of Brasero burning a compact disc.
Maybe we could call it the "Bro"? (Also, everyone knows that real hackers always have a thick layer of dust on their screens, because it makes your computer less attractive to thieves and ransomware.)

1830 hours

Food break. Danish delicacies were enjoyed. Det er dansk, det er dejligt!

1900 hours

Well, shit. The worst hardware engineers since the Apollo program had been at it again! Not being able to boot from CD-ROM on a 1995 laptop design is preposterous. In no way should my friend and I be blamed for hurtling across the plains of southern Sweden, buying esoteric storage media and writing an ISO file to it for a good ten minutes before checking if the computer was actually capable of utilizing it.

1915 hours

At this point, we scientifically and methodically started to tweak relevant parameters in an orderly fashion, working according to rigid principles of deduction and relying on our extremely broad and deep knowledge of computing in general and Thinkpads in particular. A random simpleton, such as the aforementioned store clerk, might have called it "aimlessly dicking around with jumpers and BIOS settings," but backwards and uneducated people will of course never be able to discern between madness and true genius.

Alas, some of the things we tried didn't work.

An error screen displaying a crossed-out hand, the text ERROR in capitals and the error code 00301.
An experiment we of course didn't really expect to work performed as expected.

2000 hours

Some more of the things we tried didn't work.

An error screen displaying nothing but the error code I9990305 and a blinking cursor.
Just checking to see if intentionally doing something completely wrong would trigger the appropriate response from the firmware.

2015 hours

A lot of the things we tried actually just didn't work.

A mysterious BIOS screen showing an image of a cylinder, the text HDD and a progress bar.
Despite the bar, progress was very slow.

2030 hours

By now we had deemed science in general and the scientific method in particular to be, at best, scams concocted by some of the worst thinkers since The Poetic Edda was written. Desperate times call for desperate measures and we resorted to using Windows (gasp!) and the program with the friendly and welcoming name Rufus, which made us really warm to it.

With Rufus, we created yet another supposedly bootable CF Card by using the built-in FreeDOS option, and...

IT WORKED! The computer happily booted and gave us a DOS prompt!

After taking a few minutes to congratulate ourselves on being the greatest hardware hackers since Charles Babbage designed the Difference Engine, we set about to copy the contents of our earlier, less-working FreeDOS disk image onto the new one through more traditional, file system-ish ways.

And... once again we were presented with the dots. Seven of them, to be precise. Exactly as many dots, in fact, as there are letters in the word "FreeDOS". Things finally started to make a bit of sense.

2045 hours

Once again, we Rufused (IT biz jargon) ourselves a blank FreeDOS card and copied a full FreeDOS install onto it - except for FDCONFIG.SYS, FDAUTO.BAT and KERNEL.SYS. This time we tried booting from PCMCIA by plonking the card into a Compact Flash to PCMCIA adapter - and IT WORKED!.

Copying the the full FDCONFIG.SYS and FDAUTO.BAT over once more, IT STILL WORKED!. King Carl XVI Gustaf of Sweden and John Carmack of id Software immediately telephoned us to congratulate and offer praise for our relentless work and intellectual prowess.

An IBM Thinkpad 365 finally running FreeDOS.
Long live the Victorious Heroes of the Eternal Kingdom!


Something was strange with the KERNEL.SYS file from the FreeDOS image we first used - we're not sure about the details yet. It worked fine in both DOSBox and QEMU, but it did have a different md5 sum compared to the working one. We could have gotten the very first CF card prepped with dd working if we'd only tried replacing the kernel - but hindsight is always 20/20.

The Thinkpad 365 is a really nice computer. It's sturdy, durable and well designed. The keyboard reaches levels of typing comfort we haven't seen in laptops in a long time. It's at first glance shockingly bulky, but really not that much thicker than my Lenovo IdeaPad from 2012. Working with virtualization and disk images is super easy in Linux these days. Rufus is a great little program. FreeDOS is an amazing effort in recreating a better DOS, unhindered by silly IP laws and greedy megacorps, providing an opportunity for us lovers of platforms past to relive old and create new memories of having fun with computers.

In all, we had a great afternoon and evening racing to the electronics shop, mounting Linux devices in QEMU, editing DOS system files with nothing but ECHO and TYPE, watching animated BIOS pointers and finally tasting sweet victory, booting a laptop from a PCMCIA card. And we got to eat some damn fine smørrebrød.