Microsoft has come a very long way in its fight back into the graces of all technologists. There will be some die hards that will never forgive Microsoft for what it attempted to do to open source software. Like there will be some die hards that won’t embrace PowerShell, WSL, and future Microsoft improvements. But, there is no denying that Microsoft has changed as a company in a way that is beneficial to the open source community and beyond. I’d like to share my personal Microsoft journey thus far.

Since the mid-90s, I have worked in IT in one capacity or another. Before that, I used computers routinely. I remember my childhood days on a Commodore 64 typing LOAD "*",8,1 to play the game du jour. A few years later, I recall upgrading a computer from a version of Windows 3 to Windows 3.11 because I was bored and the install disks were next to the machine. I remember in the mid-1990s when I first saw Windows ‘95 after years of DOS and Windows 3.x. It was at Forest High School in Ocala, FL. My first thought was how beautiful it was and how much easier life was going to be because of this monumental leap in the user interface.

That summer I got enough money to buy a used x86 box. I received copies of Windows and Office as gifts from folks. I was so hooked on the potential of the platform that I was tinkering with all the GUI tools. I was so enthusiastic about Microsoft I was using PowerPoint to make ad mock-ups for Redmond. They were hokey as hell but it was cool and I was a teenager. Don’t judge me, my youth was, interesting.

The next summer, I was working in an MIS department in Hendersonville, NC. That fondness for Microsoft products and long nights breaking and fixing them had turned me into a 40-hour a week IT employee for the summer. I was all in on all things PC and Microsoft. It led to me having one of the best summer jobs anyone in my school could ever have. Windows ‘98 was like the second coming of Christ. People lined up for the release of a computer operating system at a Media Play in Hickory, NC. It was a fun and exciting time in consumer computing. I remember one thing around that time that changed my life.

Internet Explorer 4 on CD-ROM was everything. The CD-ROM that came with FrontPage Express is what got me into web design and web technologies in general. I spent countless hours flipping back and forth between the WYSIWYG interface and the raw HTML view. Then cross-referencing that with the W3C specs to validate compliance. I ended up dumping FrontPage because of the non-standard compliant things it was doing for Notepad.exe. This led to my next big job in IT, a webmaster at a local ISP in Hickory, NC. My step-mom sent me to an ISP she saw an ad for on a public access channel on TV. I walked into their office to sign up for service one day. I asked for the basics for dial-up connectivity. In the days before DHCP, this was a phone number, IP addresses, and protocol configurations.

I was offered the job almost on the spot because I understood networking, Windows, and rudimentary web design. Still being in high school this job was absolutely amazing. I still talk about it today. I was proud to be a webmaster at an ISP in the late 1990s. But, by that time, IT budgets were ballooning and Microsoft was into its vision of making Microsoft products more proprietary. I saw a change coming out of necessity but still loved my Windows machine for how simple it made life. My ISP was a Windows shop. We realized continuing to go down the Microsoft Windows NT Server path was going to need a significant paying down of technical debt. We addressed some personnel issues. The ISP started using Linux after a couple of hires came in that weren’t MCSEs. I saw and fell in love with Linux’s deep toolset around networking components. I still had a Windows box on the desk behind me to help with troubleshooting but my daily driver became a Red Hat Linux 5 machine (yes, Red Hat before RHEL). 1998 was the year of Linux on the Desktop if you didn’t mind rebuilding it every once in a while. I was already writing HTML and CSS in Notepad on Windows. Jumping to jed and later vim was natural.

nmap became my favorite tool for finding oddities on our network. I had a friend at the time have his mind blown when I showed him how many open ports a Windows box on our dial-up modem network had. Then he was even more mind blown when I disconnected a box that had been idle on our network for hours with a well-formed ping. My love for Microsoft became more of a love for making showing my parents how to do things easier and less in its potential. The open source bug bit me hard; I ❤️ Linux. I remember Windows 2000 prebuilds were rolling out and Microsoft kept a box online to test against. Microsoft was calling it one of the most secure operating systems ever. History would show that wasn’t the case. I was publishing hourly nmap scans of the box and eventually, it was exploited. So much for that Microsoft security.

I joined the Air Force when the dot-com bubble burst. I was blown away that the Department of Defense was all in on Microsoft products. I was expecting a highly secure environment and got networks full of very poorly configured Windows machines. I did all kinds of annoying things on Air Force schoolhouse networks. WinPopup was my tool of choice and should never have been enabled on these networks.

I had to use and work on Microsoft products every day but I hated it. There was better tooling elsewhere that wasn’t aggressively trying to screw people over. I made every effort to use Linux in DoD. I’m pretty sure I ran one of the first Linux systems in the Air Force in 2000 during JEFX 2000. But, that’s a story for a different time.

Then Steve Balmer called Linux a cancer and set back the platform in government for a few years. When I got out of the Air Force in 2010, Microsoft had become toxic. I wanted to be in Linux environments full time. But, I still needed those damn Windows apps because that’s what a lot of folks were using (Office and Internet Explorer). I used a Windows box at work but, I spent most of my time in SSH sessions and web browsers. IE was a thorn in everyone’s side and I kept Windows so IE wouldn’t bite me too hard when I worked on solutions to problems.

Windows 8 prebuilds began rolling out. I spun up a VM running locally one night laying in bed to kick the tires on it. This is when I recognized Microsoft’s desktop/workstation days were over. I jumped back over to Linux and shortly thereafter, Mac for daily drivers. The Microsoft platform lost me likely forever at that point.

Microsoft has come a very long way since then. They haven’t won back my desktop (and they likely won’t). They will likely never win me over on servers. Their cloud offering, Azure, isn’t good enough (yet) but, it’s coming along. The fact they were at All Things Open all those years ago speaks volumes. With a booth in a prominent location and speaking on stage about how much Microsoft loves Linux; it was a breath of fresh air. Marketing folks were reaching out to people like me to figure out how best to rebuild Microsoft’s brand reputation. The fact Microsoft recognizes they messed up and are doing things to fix it says a lot.

I hope that history shows us the Balmer years at Microsoft were its time lost in the woods. The highest praise I can ever give Microsoft is saying it’s a place I would consider working if the offer ever came. We have reached that point and that says more about Microsoft’s journey than this story ever could.

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