On September 30, 2014, Microsoft announced something new and totally radical: Windows 10. Making up for the missteps of Windows 8, Windows 10 was set to be the first major release that's totally free to most existing users. Beginning the next day, you could install the first Windows 10 Technical Preview (the term "Insider Preview" came later), as part of the all-new Windows Insider Program.

Over the years, the program saw several leadership changes, as things tend to over the course of over a decade. And through the years, I've become friends with some of the fine folks who worked on the team. At conferences like Microsoft Build and Ignite, I, along with other journalists on the Microsoft beat, used to hang out at the Windows Insider Program booth, chatting with the team about Windows, work, life, or anything else. We'd chat with attendees too, and I learned a lot about the different relationships users have with the operating system we all know.

All of those people are gone now.

Everyone has moved on

No more taco hats, ninja cats, or big red buttons

On September 19, Star Trek and Dr Pepper enthusiast Brandon LeBlanc moved on to a Director of Communications role for Windows and Devices in Microsoft. The man had penned Windows Blog posts, and was one of the primary voices on social media interacting with Insiders on social media. On November 10, dog-lover and unfortunate Texas Rangers fan Jason Howard moved on to another role within the company. The two were partners in crime, serving as the faces of the program throughout changes in leadership.

On November 3, Amanda Langowski, who's always been quieter on the public side of things, also moved to another role within the Windows and Devices team. Amanda was the third chief of the Windows Insider Program, following Gabe Aul in the very beginning (now at Meta), and fashionista Dona Sarkar. This marks the first time the leader of the program has left, and an immediate successor was not named.

When Gabe Aul left, there was a press release, and a photo op of him handing Dona the "big red button", which was symbolically used to push new builds of Windows. I remember that it happened in the spring too, because Dona's Twitter banner showed her at the Microsoft Build sign, pushing it. Yes, she was pushing a build.

The Windows Insider Program still exists, but I don't know the names of anyone that works on the team anymore. And I apologize for that, because I'm sure I've met them before, or they're slipping my mind right now. But the trio that served as the main characters are gone.

The Windows Insider Program used to be fun

It was the new hotness, as the kids say

The early days of Windows 10 were wild, because no one really knew what it was going to be. Microsoft held that one event in September, but the more through reveal was in January 2015. The first Windows 10 Technical Preview was essentially Windows 8 with a regular Start Menu. And coming off of Windows 8, people were pretty hyped.

New Windows 10 builds arrived roughly every month, assuming you were in the Fast Ring. Yes, there were Fast and Slow Rings before there were Canary, Dev, and Beta channels. The Slow Ring was meant to be more stable. When Dona Sarkar took over and we started getting Fast Ring builds weekly, Slow Ring builds were supposed to be monthly. That never actually worked out, one of the reasons they moved to the channel system that doesn't align with a speed.

When it started, Gabe Aul had just six Twitter followers, notably saying, "and I think one of them was my mother." When he moved on, he had 130,000. I remember someone making a video that used John Cena's entrance and music, changing the name to Gabe Aul, and putting Gabe's face on it.

It was fun.

Windows 10 was filled with big promises too, so if you were an enthusiast, it was exciting. The personality and whimsy around the Insider Program was easy to rally around.

It stopped being fun

The OS stopped being interesting too

After Windows 10 shipped in July 2015, there was a new problem. How do you keep people pumped, in the famous Microsoft lingo, about a product that's now getting updated. There were no major redesigns coming, and fewer major features coming. The major version of Windows had shipped.

It didn't happen all at once. The fall update that year was seen as the real Windows 10 release, with the OS pushed early in July for OEMs. There were still new features to come, and after that, there were fewer new features, and after that, there were even fewer.

Things also got, well, annoying. The Windows Insider Program started doing controlled releases with new features, something that was universally hated. Those early builds of the OS were unstable, so when you put the stability of your system at stake in order to be first in line for new features, it really stings when you install the build and don't actually get the thing you wanted.

In the fall of 2017, Microsoft decided to just go ahead and ship the Windows 10 Fall Creators Update, completely skipping the Release Preview Ring of the Windows Insider Program. It did not go well. The company had to pull back the update because some people's files were getting deleted.

There were no rules anymore. The social contract was broken. The Windows Insider Program was formed as a community, a passionate group of Windows users that would help to shape the future of the OS. At that point, Microsoft was treating us like common QA testers, with the exception being that Insiders weren't on the payroll.

The updates got even more minor as time went on. Windows 11 arrived in 2021, and that was a bit of a resurgence, especially since PC sales were surging thanks to so many people moving to working from home. But even then, once it shipped, there was little else coming.

Today, it seems like every piece of Windows news revolves around AI, and more specifically, Copilot. And frankly, it's all stuff that's tough to get excited about.

It's just an open beta program now

The whimsy is gone, and it's sad

Ever since Microsoft pushed Azure as hard as it did, in order to become a cloud services company, and now with its push for AI, Windows goes through cycles where it's a priority, and then it's not. Windows 10 was a huge release, and then OS efforts were essentially in maintenance mode. Then, people started working from home and Windows 11 was rushed out of the gate. After that, things have been a bit dull, and now there's the Copilot/AI push. It's all ups and downs.

That's really not what this is about. Some of my favorite memories at Microsoft events will always involve the Windows Insider Program, and since everyone I knew left, I'm faced with the reality that I won't make new memories like that.

The Windows Insider Program continues to exist, but it's just an open beta program that you can enroll in from Settings. There won't be meetups anymore, not that there have been in a long time.