On September 30th, 2014, Microsoft announced Windows 10. The next version of Windows at the time was crazy for multiple reasons, but one of the most notable things Microsoft introduced at the time was the Windows Insider Program. It's a staple of Windows development today, but back then, testing early versions of Windows was something only a very few select people could do.

Ten years on, the Windows Insider Program has changed a lot, and there's no better time to reflect on this journey than this momentous anniversary.

Exciting beginnings

Being an Insider was so much fun at first

The start of the Windows Insider Program was intrinsically exciting. Going from the very limited testing phases of previous versions of Windows to a program anyone could sign up for was something no one could really expect. In fact, I recall hearing that even people inside Microsoft didn't think the program was going to be open to everyone. Most were expecting some kind of cap on the maximum number of users right up until the last minute.

It was particularly exciting to be able to test the future of Windows after the Windows 8 generation drove so many people away, with Windows 10 promising to right the wrongs of that era and bridge the gap between tablet and desktop users.

The first build of Windows 10 was made available on October 1st, 2014. At the time, they were called Windows 10 Technical Preview, which indicated that the Insider Program was still oriented for the more technically apt users with a keen interest in Windows development. Kicking things off with build 9841, Windows Insiders only received a total of three preview builds in 2014, including that first one, but each one was packed with big changes that had everyone excited. That first build was very much like Windows 8, except the Start menu was now contained in the corner of the screen, and "Metro" apps opened in Windows rather than taking the full screen. But soon we'd start seeing things like new icons for system resources and more in-depth changes that shaped Windows 10 into a totally different operating system.

The waiting times between builds really made things all the more exciting. At the time, the program was led by Gabriel (Gabe) Aul, and we'd often wait four to six weeks for a new Windows build, which legitimately felt like testing something unfinished and looking into the future of Windows. On weeks when we did get a new build, Aul would tease his followers on Twitter with the build number for that week appearing in different contexts. It made it truly fun to watch his Twitter profile waiting for that number to show up somewhere.

A change in leadership

And a loss of excitement

While the wait times did make new builds more exciting, a lot of people were very impatient when it came to getting new builds, and from early on, Microsoft had discussed the idea of a faster cadence of builds for Insiders that chose to do so. This didn't happen for a while, at least not in a significant way.

You can trace the true start of this change to June 2016. At this time, Gabriel Aul stepped down as leader of the Windows Insider program and eventually left Microsoft altogether a few years later. Dona Sarkar, who had also been working on Windows for many years, replaced Aul as leader of the Insider program, and you could tell there was a big change in the way the program was treated. Over time, builds started being released more and more frequently, and the same can be said for Windows 10 updates, which became semi-annual from 2017 onwards.

Microsoft eventually introduced the Skip Ahead channel to release builds to Insiders that much faster, before eventually giving up on that idea. At some point, we basically settled on receiving new builds for the Fast Ring (now called Dev channel) basically every week, with the number of new features in each one naturally being much smaller, though a Canary channel was introduced more recently, in 2023. The predictable cadence and the reduced number of new features in each build definitely made for a less exciting program than it was in the beginning.

Microsoft also started to be somewhat more careless with how it tested Windows 10 releases prior to launch. The Insider program already felt like a sort of replacement for paid internal testing teams, relaying that responsibility to the volunteering insiders, but Microsoft also didn't take enough feedback. Windows 10 version 1803 had already caused issues for a lot of users at launch, but by the time we got to version 1809 in late 2018, Microsoft decided to release the update without even testing it in the Release Preview channel first. Many users who installed the update found that their files were gone completely, which resulted in the update being paused while the issue was worked out.

It was a dark time for the Insider program, where the excitement for new builds was getting lower and lower, while it felt like the end result of that public testing was increasingly less polished. After 2018, Windows 10 updates became even less exciting. New features were few and far between, and some feature updates were basically just enablement packages that changed almost nothing about the OS.

Making the program meaningless

A/B testing ruined the point of Insider channels

In the early days, the Insider program felt like it genuinely gave users an early look at what Microsoft was cooking up for Windows 10, and it truly felt like we were seeing things before we were supposed to. The OS was less stable and less reliable, but it was more fun as a result, and new features legitimately took users by surprise.

But at some point, Microsoft decided that this somehow wasn't good enough. Maybe the builds were too unstable for users, or maybe these builds were spoiling surprises. Either way, the result was that Microsoft no longer wanted to make features available to Insiders as they were developed, and instead, the company started holding them back. Using a mechanism known as feature IDs, the company would often implement features in Insider builds that were disabled for users, so it could control when users would see those features. Of course, solutions like mach2 and ViveTool cropped up to enable feature IDs and make those features visible, but for most people, this meant the Insider program was a lot more boring now.

New Windows features will often only show up after Microsoft has made a big announcement out of them, and many times, rather than appearing in the Canary or Dev channel first, they'll appear simultaneously for every Insider channel. Sometimes they can even show up in the Beta or Release Preview channels before the Dev channel. Choosing a channel doesn't mean anything anymore. Sure, the features you get might change, but it's almost never because a certain feature is earlier in its development stages. It's all just about when Microsoft wants to make those features visible to you, regardless of the channel you choose.

Hello, Windows 11

Finally, the Insider program was exciting again

Thankfully, in 2021, Microsoft reinvigorated Windows and the Insider program with the introduction of Windows 11 on June 24th. Windows 10 had felt moribund for years at this point, and Windows 11 was a radical change. There was a completely new UI paradigm and tons of new features like Android apps. Windows Insiders got first dibs on the new Windows 11 features, and it was a truly exciting time once again. The initial preview build of Windows 11 was a huge deal, but even after that, the Insider program had a bit more life in it as more of the announced Windows 10 features were still rolling out, on top of other surprises.

Things like a refreshed UI for Paint (and eventually a dark mode), Clock with Focus Sessions, Widgets, and Android apps were all rolling out gradually, which made Windows 11 that much more fun to experience as an Insider. That has generally kept going all the way through today. The features we're getting a lot of the time are a bit less exciting, but there are still a lot of notable changes only available to Insiders at any given moment. You can probably attribute some of that excitement to the resurgence of Arm devices and the introduction of Copilot+ PCs this year, but hey, it's something.

Windows 11 testing is still plagued by the same issues with A/B testing, though, so the program still feels kind of pointless and not well thought out. But at least it's nice to see actual features being added now. Hopefully, Microsoft will manage to keep things interesting for Insiders testing Windows 11 going forward.

Has the Windows Insider channel lost its way?

What made it exciting was ultimately its downfall

Everyone will have different outlooks on the evolution of the Windows Insider program, but my perspective is that it lost a lot of the meaning it originally had, and I think that's owed in part to the program being as open as it is. I'm not one for gatekeeping anything, but opening the Insider program up to everyone was part of the problem. When it first started, while it was open to everyone, it was clear that the program was still aimed at the more technically-inclined users. those who don't mind bugs and crashes in order to test new features. That's what most beta testing programs are.

But a lot of the users who joined are probably not that technically inclined, and the feedback they provided was often very vocal about things that are to be expected in a beta program. A lot of people wanted the program to be usable by anyone, and that meant Microsoft had to sterilize the program until it eventually was nothing but a shell of its original vision. People wanted builds more frequently, so they became a weekly occurrence (almost daily, now that multiple channels get builds in different ways). But that means each new build includes very little that's new and there's no excitement in waiting for a build anymore. Those teases with a random build number showing up on Twitter wouldn't really work, because it's always more or less expected we'll get a build that week, and it's likely not much cause for celebration at all.

At the same time, Microsoft became too eager to control the narrative around new Windows features, maybe because many of the people in the Insider program didn't understand that features being tested could come and go at any given moment. Microsoft stopped wanting to deal with that kind of feedback, so it streamlined everything to make features available to Insiders only when they're nearly guaranteed to be coming to a final release a few weeks or months later.

But the way I see it, beta testing isn't meant to be fun. It's fun for people like you or me, who enjoy using worse versions of a product in exchange for learning little tidbits about the future, but at its core, it's just a necessary part of the development process. But it feels like Microsoft wanted the Insider program to be a mainstream thing, and you can't really please both of these audiences at the same time.

Maybe it's time for a reboot

Back in the earlier days of the Insider program, when the Xbox team first implemented it, there was a system that rewarded the more active Insiders. Unlike on Windows, Xbox Insiders were only allowed to sign up for the more advanced channels if they provided great feedback in the less exciting ones. While I think this approach was maybe a bit too restrictive, I now see some merit in it.

Microsoft might be able to make the Insider program more exciting again if it can filter the users who sign up for it a bit more. If it can create a mechanism where Insiders will only join the Dev channel if they're technically proficient and understand the risks, maybe the company can become comfortable releasing more unstable builds with more untested features again. I think this would go a long way in making the program more exciting again.

As we celebrate 10 years of the Insider program, maybe a reboot is warranted. A fresh start for Windows Insiders could be just the thing to bring back that joy of testing Windows 10 after it was first announced.