I never would have imagined myself in an arm-wrestling match with the floppy disk drive. But sitting where I did in Windows setup, that’s exactly what happened. A few times.

When I had started at Microsoft, a boot floppy was critical to setting up a new machine. Not by the time I was in setup. Since Remote Installation Services (RIS) could start with a completely blank machine, and you could now boot a system to WinPE using a CD, there were two good-sized nails in the floppy diskette’s coffin.

Windows XP was actually the first version of Windows that didn’t ship with boot floppies. It only shipped with a CD. While you could download a tool that would build boot floppies for you, most computers that XP happily ran on supported CD boot by that time. The writing was on the wall for the floppy diskette. In the months after XP released, Bill Gates made an appearance on the American television sitcom Frasier. Early in the episode, a caller asks about whether they need diskettes to install Windows XP. For those of us on the team, it was amusing. Unfortunately, the reality was that behind the scenes, there were some issues with customers whose systems didn’t boot from CD, or didn’t boot properly, anyway. We made it through most of those those birthing pains, though.

It was both a bit amusing and a bit frustrating to watch OEMs early on during the early days of Windows XP; while customers often said, “I want a legacy free system”, they didn’t know what that really meant. By “legacy free”, customers usually meant they wanted to abandon all of the legacy connectors (ports) and peripherals used on computers before USB had started to hit its stride with Windows 98.

While USB had replaced serial in terms of mice – which were at one time primarily serial – the serial port, parallel port, and floppy disk controller often came integrated together in the computer. We saw some OEMs not include a parallel port, and eventually not include a floppy diskette, but still include a serial port – at least inside – for when you needed to debug the computer. When a Windows machine has software problems, you often hook it up to a debugger, an application on another computer, where the developer can “step through” the programming code to figure out what is misbehaving. When Windows XP shipped, a serial cable connection was the primary way to debug.  Often, to make the system seem more legacy free than it actually was, this serial port was tucked inside the computer’s case – which made consumers “think” it was legacy free when it technically wasn’t. PCs often needed BIOS updates, too – and even when Windows XP shipped with them, these PCs would still usually boot to an MS-DOS diskette in order to update the BIOS.

My arrival in the Windows division was timely; when I started, USB Flash Drives (UFDs) were just beginning to catch on, but had very little storage space, and the cheapest ones were slow and unreliable. 32MB and 64MB drives were around, but still not commonplace. In early 2002, the idea of USB booting an OS began circling around the Web, and I talked with a few developers within The Firm about it. Unfortunately, there wasn’t a good understanding of what would need to happen for it to work, nor was the UFD hardware really there yet. I tabled the idea for a year, but came back to it every once in a while, trying to research the missing parts.

As I tinkered with it, I found that while many computers supported boot from USB, they only supported USB floppy drives (a ramshackle device that had come about, and largely survived for another 5-10 years, because we were unable to make key changes to Windows that would have helped killed it). I started working with a couple of people around Microsoft to try and glue the pieces together to get WinPE booting from a UFD. I was able to find a PC that would try to boot from the disk, and failed because the disk wasn’t prepared for boot as a hard disk normally would be. I worked with a developer from the Windows kernel team and one of our architects to get a disk formatted correctly. Windows didn’t like to format UFDs as bootable because they were removable drives; even Windows to Go in Windows 8.1 today boots from special UFDs which are exceptionally fast, and actually lie to the operating system about being removable disks. Finally, I worked with another developer who knew the USB stack when we hit a few issues booting. By early 2003, we had a pretty reliable prototype that worked on my Motion Computing Tablet PC.

Getting USB boot working with Windows was one of the most enjoyable features I ever worked on, although it wasn’t a formal project in my review goals (brilliant!). USB boot was even fun to talk about, amongst co-workers and Microsoft field employees. You could mention the idea to people and they just got it. We were finally killing the floppy diskette. This was going to be the new way to boot and repair a PC. Evangelists, OEM representatives, and UFD vendors came out of the woodwork to try and help us get the effort tested and working. One UFD manufacturer gave me a stash of 128MB and larger drives – very expensive at the time – to prepare and hand out to major PC OEMs. It gave us a way to test, and gave the UFD vendor some face time with the OEMs.

For a while, I had a shoebox full of UFDs in my office which were used for testing; teammates from the Windows team would often email or stop by asking to get a UFD prepped so they could boot from it. I helped field employees get it working so many times that for a while, my nickname from some in the Microsoft field was “thumbdrive”, one of the many terms used to refer to UFDs.

Though we never were able to get UFD booting locked in as an official feature until Windows Vista, OEMs used it before then, and it began to go mainstream. Today, you’d be hard pressed to find a modern PC that can’t boot from UFD, though the experience of getting there is a bit of a pain, since the PC boot experience, even with new EFI firmware, still (frankly) sucks.

Computers usually boot from their HDD all the time. But when something goes wrong, or you want to reinstall, you have to boot from something else; a UFD, CD/DVD, PXE server like RIS/WDS, or sometimes an external HDD. Telling your Windows computer what to boot from if something happens is a pain. You have to hit a certain key sequence that is often unique to each OEM. Then you often have to hit yet another key (like F12) to PXE boot. It’s a user experience only a geek could love. One of my ideas was to try and make it easier not only for Windows to update the BIOS itself, but for the user to more easily say what they wanted to boot the PC from (before they shut it down, or selecting from a pretty list of icons or a set of keys – like Macs can do). Unfortunately, this effort largely stalled out for over a decade until Microsoft delivered a better recovery, boot, and firmware experience with their Surface tablets. Time will tell whether we’re headed towards a world where this isn’t such a nuisance anymore.

It’s actually somewhat amusing how much of my work revolved around hardware even though I worked in an area of Windows which only made software. But if there was one commonly requested design change request that I wish I could have accommodated but couldn’t ever get done, it was F6 from UFD. Let me explain.

When you install Windows, it attempts to use the drivers it ships with on the CD to begin copying Windows down onto the HDD, or to connect over the network to start setup through RIS.

This approach worked alright, but it had one little problem which became significant. Not long after Windows XP shipped, new categories of networking and storage devices began arriving on high-end computers and rapidly making their way downmarket; these all required new drivers in order for Windows to work. Unfortunately, none of these drivers were “in the box” (on the Windows CD) as we liked to say. While Windows Server often needed special drivers to install on some high-end storage controllers before, this was really a new problem for the Windows consumer client. All of a sudden we didn’t have drivers on the CD for the devices that were shipping on a rapidly increasing number of new PCs.

In other words, even with a new computer and a stock Windows XP CD in your hand, you might never get it working. You needed another computer and a floppy diskette to get the ball rolling.

Early on during Windows XP’s setup, it asks you to press the keyboard’s F6 function key if you have special drivers to install. If it can’t find the network and you’re installing from CD, you’ll be okay through setup – but then you have no way to add new drivers or connect to Windows Update. If you were installing through RIS and you had no appropriate network driver, setup would fail. Similarly, if you had no driver for the storage controller on your PC, it wouldn’t ever find find a HDD where it could install Windows – so it would terminally fail too. It wasn’t pretty.

Here’s where it gets ugly. As I mentioned, we were entering an era where OEMs wanted to ship, and often were shipping, those legacy-free PCs. These computers often had no built-in floppy diskette – which was the only place we could look for F6 drivers at the time. As a result, not long after we shipped Windows XP, we got a series of design change requests (DCRs) from OEMs and large customers to make it so Windows setup could search any attached UFD for drivers as well. While this idea sounds easy, it isn’t. This meant having to add Windows USB code into the Windows kernel so it could search for the drives very early on, before Windows itself has actually loaded and started the normal USB stack. While we could consider doing this for a full release of Windows, it wasn’t something that we could easily do in a service pack – and all of this came to a head in 2002.

Dell was the first company to ever request that we add UFD F6 support. I worked with the kernel team, and we had to say no – the risk of breaking a key part of Windows setup was too great for a service pack or a hotfix, because of the complexity of the change, as I mentioned. Later, a very large bank requested it as well. We had to say no then as well. In a twist of fate, at Winternals I would later become friends with one of the people who had triggered that request, back when he was working on a project onsite at that bank.

Not adding UFD F6 support was, I believe, a mistake. I should have pushed harder, and we should have bitten the bullet in testing it. As a result of us not doing it, a weird little cottage industry of USB floppy diskette drives continued for probably a decade longer than it should have.

So it was, several years after I left, that the much maligned Windows Vista brought both USB boot of WinPE and also brought USB F6 support so you could install the operating system on hardware with drivers newer than Windows XP, and not need a floppy diskette drive to get through setup.

As I sit here writing this, it’s interesting to consider the death of CD/DVD media (“shiny media”, as I often call it) on mainstream computers today. When Apple dropped shiny media on the MacBook Air, people called them nuts – much as they did when Apple dropped the floppy diskette on the original iMac years before. As tablets and Ultrabooks have finally dropped shiny media drives, there’s an odd echo of the floppy drive from years ago. Where external floppy drives were needed for specific scenarios (recovery and deployment), external shiny media drives are still used today for movies, some storage and installation of legacy software. But in a few years, shiny media will be all but dead – replaced by ubiquitous high-speed wired and wireless networking and pervasive USB storage. Funny to see the circle completed.