Should Microsoft brag about Windows Insider Program success after its October Update mess?

Surface Insider Rings
Surface Insider Rings (Image credit: Windows Central)

In early October, Microsoft announced its next major Windows 10 "feature update," appropriately named the Windows 10 October 2018 Update. It started rolling out the update shortly thereafter to users who actively sought it out (it was not available unless you used a tool to fetch the update). A major issue with the build soon arose, causing users to lose data and leading Microsoft to pull the update.

So what exactly happened? Our Senior Writer Zac Bowden did some digging to find out, and you can read the details here. Short answer: Microsoft mistook the early reports of issues for another bug that had already been squashed. So it continued to roll out the update, oblivious to the fact that a significant file-deletion bug still existed. So you could argue the Windows Insider Program failed, or that Microsoft did in its response to reports of issues. It took weeks for the problem to be resolved, and the "October Update" was not publicly released again until November.

Ever since, some people on the Windows Central team have debated exactly what happened and who's to blame. In particular, Gaming Editor Jez Corden and Contributor and app reviewer Sean Endicott have felt particularly strongly, with opinions that occupy completely different ends of the spectrum. A keynote address from Windows Insider Program Chief Dona Sarkar, at the European SharePoint Office 365 & Azure Conference late last month in Copenhagen, Denmark, brought the debate to a head. (Sarkar happens to be one of our 80 must-follow 2018 Microsoft Influencers.) Sarkar's speech was about how other companies can and should mimic Microsoft's Insider program to ensure successful software releases, and it came on the heels of the October Update mishap.

Endicott argues that it's a very bad look for Sarkar and Microsoft to be touting the Insider Program's success right now, while Corden believes one mistake shouldn't sour the success of the program to date. Below you'll find those two arguments fleshed out a bit. Which side do you stand on? Let us know in the comments.

Time for damage control, not boasting

Microsoft's Dona Sarkar

Microsoft's Dona Sarkar

From Endicott:

My issue isn't with the Windows Insider Program helping Microsoft gain feedback from users, it's how people at Microsoft seem to view it. Slides and presentations from Sarkar about how "insidering" software guarantees the successful rollout of software are both inaccurate and tone deaf to recent issues with Windows 10 and its update process.The presentation that sparked this conversation, by the head of the Windows Insider program, immediately drew attention on Twitter. Sarkar should understand more than anyone that the Windows Insider Program did NOT ensure the smooth rollout of the October 2018 Update. Sure, Microsoft has had success using Insiders for Office and Xbox releases, but that doesn't mean that Insider programs ensure smooth rollouts. Far from it.Windows Insiders spotted bugs that contributed to the delay of the October Update rollout, and those seem to have been ignored. Furthermore, the Release Preview Ring for Insiders was completely skipped over before attempting a large-scale rollout. Why did Microsoft create the Release Preview Ring if it wasn't going to be a last line of defense for spotting issues?There's definitely a role for the Windows Insider program, but the people at Microsoft need to remember what it is, and it isn't a replacement for a QA department. It can help gain meaningful feedback and bug reports from users, but that most certainly doesn't guarantee the smooth rollout of software, particularly software on the scale of Windows 10.(As an aside, I've seen many comments on the web criticizing Dona Sarkar in a sexist and inappropriate way. I think this is both morally wrong and counterproductive to creating meaningful change.)

Corden took a contrary stance ...

One mistake should not define the Insider Program

From Corden:

The spotlight has been on the Windows Insider program since the October 2018 update fiasco, but is it really a "fiasco"?In October, Microsoft revealed that less than one one-hundredth of one percent of users, in very specific conditions, had lost some of their files. Data loss sucks, even if it's affecting just a small subset of users, but the ramifications for Microsoft were fairly broad. Mainstream media covered the issues, which put a target on Microsoft's back, specifically the Windows Insider Program.Microsoft has philosophically been at odds a bit with users over how it handles Windows 10 updates. Those updates are incredibly crucial for the OS to remain secure given the modern-day hacking arms race. The way Microsoft updates Windows might seem inconvenient at times, but it's crucial for the health of the OS, particularly since Redmond seems to have done away with big packaged Windows updates it can sell every few years. It's that sense of inconvenience that leads many of us to ask, What's the point of the Windows Insider Program if it can't prevent these sorts of issues?The reality is it can and it does prevent these sorts of issues. Thousands of them, every year. For a single (but, yes, major) flaw to slip through the cracks, it isn't worthy of some of the outrage I saw spilling all over Twitter, particularly when it was directed at individuals. Even more so when it comes to personal attacks. But that shouldn't even be up for discussion . Does this whole situation warrant all the angry criticism of the Insider Program? Not even slightly.Microsoft is also using Insider Programs for both Xbox One and Office, as well as other software and services it has. The amount of users in those respective programs is far lower than that of Windows, however, and arguably far less complex. Given the bulk that makes up Windows, it's a little remarkable that it works as well as it does.Constructive feedback is always useful, and Microsoft has responded with a wide array of new measures it's going to leverage to prevent the data-loss issue from happening again. But the deluge of entitlement and internet tears over this problem, particularly by those unaffected, has been a little bit silly to digest. Microsoft has plenty of reasons to tout the quality of its Insider Program, across every product where it lands, and the team that works on it should be proud that they, frankly, remain sane despite the deluge of rude, disrespectful whining that makes its way in their direction.The October problem is something that simply doesn't happen often, and I think Microsoft can (and should) be afforded a few mistakes every now and then. To err is human, and human is very much what modern Microsoft is.

Where do you stand?

Do you think it's a big deal that a bug like the one that made Microsoft pull the October Update for weeks after its release slipped through? Should Microsoft still have its employees doing keynote addresses about the Insider Program's success in light of the recent issue? And do you tend to side with Endicott or Corden on the subject? Share your take in the comments.

Sean Endicott
News Writer and apps editor

Sean Endicott brings nearly a decade of experience covering Microsoft and Windows news to Windows Central. He joined our team in 2017 as an app reviewer and now heads up our day-to-day news coverage. If you have a news tip or an app to review, hit him up at (opens in new tab).

  • The Insider Program does help a lot, but there is no need to hype it up. You will get people joining it that don't understand they are getting buggy early versions of an update, and they'll trash the OS instead of realizing the choice they made. Too often I see users blaming Windows for an issue a program, or they, caused. That type of person in the Insider Program would do more harm than good. I was a part of the program on my Lumia devices, but I need my computer to work reliably. I don't intend on joining the program for desktop use.
  • I think MS has every right to boast about this. What other company has anything even remotely like it? I’ve personally had response from MS to feedback given. And they’ve actually fixed things as a result. As I’m sure a number of folks have had here. They take the program seriously. Kudos to them for implementing it.
  • I agree. Massive storm in a tea cup for a very fringe case of data loss (who doesn't back up anyway!)
    A handful of QA testers inside MS is no comparison for hundreds of thousands of real users.
    They probably run internal testing anyway (unit testing) and leave experiential testing to insiders and their own employees presumably.
    Bit of a nonsense this insider program bashing if you ask me.
  • not that I don't agree with what you said but I think most people backup to cloud services like OneDrive. So if you're backing up to OneDrive and there's a bug that deletes your onedrive data then backing up is kinda moot at that point. I got hit with the bug it wasn't that big of a deal. Your data is still there it's just no longer in your OneDrive. It's somewhere in your computer
  • Speaking only for myself, I hope they don't end the program. Hyping it? Maybe they should dial that back a bit, but perhaps the better path would be to put better telemetry in the builds until they are ready for production release and then yank the extra telemetry. When I sign up for the Skip-ahead ring, I know full well I'm walking into a potential minefield.
  • I'm positive they won't END the program. They would not want to mention it at all, if they had plans to shut it down :) But I agree, they should not had hyped it so soon after the backlash. And not in Denmark, where I perceive the majority of Danish enterprises stance on Windows as "Give me 7 or get out". I have never seen a corporate device running Windows 10 in Denmark, I am sure they exist, but that they are so hard to spot tells you a lot about the adoption rate.
    That, and the fact that Danish Feedback Hub top-5 voted feedback can be summarized to "Why have you not given us Cortana yet?".
    Don't interpret all that as rude, it's only meant to establish how disconnected the Danes are from this program and Windows 10 in general and thusly prove that Microsoft cannot assume the same PR-statements works outside of the US, and that they should research how their own product exactly work (or doesn't) before doing their selling.
  • I wonder how many Insiders sign up for the sole purpose of getting the builds earlier. I was one of those. I never gave feedback, but I enjoyed the early updates. I am an IT tech so I can resolve my own problems. If something didn't work correctly, it usually wasn't an issue for me to either resolve it or roll back.
  • Do the greater good and report issues. The program in that iteration only worked when volume of reports was taken into account because severity was not a metric they were tracking. It sucks to have to join Insider program to ensure basic functionality of Windows 10 remains working, but it a necessity since Microsoft can't seem to get it right on their own.
  • The Insiders Program is absolutely vital to the Windows as a Service model. The issues were serious yes... for a tiny fragment of the population. But MS recovered the files. And personally I think this whole thing was overblown by the old-guard anti-MS haters that still cling to the old days like hardliners to the cold-war. Bottom line... There’s no way we can go back to the way it was. While I agree MS could clean up Feedback, by grouping common threads together, and by having more humans monitoring it rather than AI algorithms, Feedback Hub and the Insiders Program is still a key part of keeping Windows relevant in a fast paced world.
  • Total 19H1 slow ring builds rec'd to date: 0
    my purpose in participating in the Insider Program is to familiarize myself with changes to Windows well before my tech support customers encounter them for the first time. If only it actually worked.
  • > [Windows 10 October 2018 Update] was not available unless you used a tool to fetch the update The tool was called "Windows Settings" ... just sayin'
  • He's talking about Update Assistant and/or Creation Tool.
  • Hopefully not, because that would mean that he forgot to buy a clue before setting out to write an article. First wave *was* available through Settings/Windows Update -- I have updated two machines before they stopped a rollout, one of them is still 1809, the other one had to be rolled back due to the issues streaming Steam games.
  • Microsoft always believes their own bullshit. Eat dog food , yum, yum. Insiders bla bla is great.
    Look, you made an egregious mistake and some level of contrition with positive corrective action is warranted sans any bragging. Show some quality metrics from an independent source demonstrating marked improvement and then you can brag, a little.
  • Things are definitely not where they should be. What I would like to know is, please show me where MS fired the entire QA department. I have heard many say this around the internet but I have seen no one show me that it actually occurred.
  • There was movement, but I don't think all were let go, just given other responsibilities. However, that did mean Microsoft was relying more on the Insider Program to find and report issues. That was a good thing, but they should have gotten the bugs out of the Insiders Program and verified that it was just as effective before making those staffing changes.
  • Nope. Now with all of the problems people are having updating to the Fall release. Just say nothing, and deny everything!
  • MSFT does not encourage use of primary or production devices in an Insider testing scenario. Yet that would almost be necessary in order to catch some of the bugs. Virtual machines and regular devices kept out of a production environment simply don't get used in as rigorous ways. The Insider Program is an important tool in debugging and in usability feedback, but the selfhost testing stage is probably what failed in the recent problems. Perhaps that is what needs work (or perhaps some overhauling). That could be a long-range project indeed.
  • I think most people in the insiders program fast ring run it on a secondary machine until it's stable then drop it on their primary machine. I agree you need it on your primary to catch most things but early builds are usually pretty buggy and aren't good to run on your primary machine.
  • I'm going to have to either see the transcripts of the speech, hear it or see it before making any detailed comments about the speech - Ideally I'd like to see the speech as body language, verbal tone, eye movement etc speak volumes. One of the issues I have is that Microsoft took constructive plus very honest feedback on WM10 and decided to chop many phones off the eligible upgrade list. Many which were able to run the new versions at the time of release without issues suchas the creators update Secondly, many items of feedback are left unanswered or addressed on the feedback hub for insiders - this understandably due to the lack of resources and coding hours available since there is no actual dedicated team for quality assurance and programmatic testing. After the firing of quality assurance and programmatic testers, that was one of the reasons I stopped being an Windows Insider as I felt my feedback would hardly be acted upon. To provide some general perspective for many of the comments: Not many understand logistics of the back end side of any organisation - how it actually runs, the processes and policies in play. As well as pyschological, philosphical and physiological factors that govern everyones subconcious and bias - which is why people perceive different and that forms one aspect of our personality. It's more evident in twins, who may look the same but may have differing personalities. The most easiest identifier is accents, you only notice it if you venture out to different regions or countries etc. As people simply do not think in multiple perspectives let alone see things from multiple angles at once, it's not something a person is born with it's a skill that you learn through experience and some are inherently better at it than others due to their empathic nature. Hence the sexist comments from members of the public, most of these people mostly live in their own bubble. I say most, I know a few people who inherently biased against the members of the opposite gender but are insightful in other aspects - just not empathy. That is most probably attributed to the toxic macho stigma that boys grow up with and that is not their fault. It's been happening through centuries as for time immemorial men were seen as the bread winners and it was frowned upon when women worked let alone able to vote. Back to Microsoft for context on the above: In regards to Microsoft, they took one of the beloved features of the panaromic photo roll of favourite photos and replaced it with a grid of thumb nails, as due to telemetry data people went to the album section most of the time after opening the photohub. Another example, the reduced the search key into a glorified QR scanner before it became the dedicated key for Cortana. Here is another, they deemed it was unnecessary to have a file explorer - which meant you couldn't attach files with office apps on Windows phone 8.x in email chains as pressing the attachment button defaulted to the photohub. You could only share to one email, share to your own email and forward or resort to onedrive links for instance. Another example is the removal of kids corner, again based on telemetry data. This caused me countless number of issues as it was a major USP for many parents choosing windows phone over ios and android. As it enabled them to have control over what apps their kids used, personally I am against giving any toddler or baby an electronic tablet or phone to play with - they should be given instruments, rattles, shape puzzles and electronic toys that speak multiple languages instead. I have seen the direct result of children reared on smartphones and tablets, I've had to baby sit them for a time. The live lock screen functionality - that never materialised fully. The other notable example is the action centre, which came after much public outcry as live tiles were deemed suitable replacements. They were not, as counters don't go beyond 99, the unread number is lost once the email app is open and so you have to have read all the emails if you want to keep track - imagine those with ocd.... and not to mention you lose the notification if the app was not pinned to the start screen. The biggest of all is the consumer retrenchment and apparently they didn't think they get hammered that badly. Then we have CEO's track record of not following through on his word, he said if OEM's don't build phones, Microsoft will and later proceeds to axe the mobile division. As a result UWP has been left languishing... there hasn't been much improvement on that front since then either. The lack of investment in team doing localisation for Cortana is also another prime example of risk averseness and poor fiscal management. The availability of Surface devices is another - as for a long time it was only available in limited markets and that was to minimise financial out lay - poor fiscal management albeit they were profitable. That is due to the insane engineering talent at Microsoft and Microsoft research. Microsoft got a few factories with the Nokia d and s acquisition, with these they could have had complete control over the supply chain, financial outlay and component sourcing contracts. Which would have allowed them to completely fine tune the direct level integration between the software and the hardware. All these decisions are devoid of customer perspectives and empathy. Not to mention, the current CEO touted his lesson on empathy was when an interviewer asked him what he would do if he say a abandoned child and his response was he would call 911. To which the interviewer replied, he should have comforted the child - something along these lines. Which is just baffling... Going back to the topic at hand - The speech. If it does seem like it was bragging and there is no mention about the issues of the October 2018 update as well as the misteps then it's more likely damage limitation (As well as the lack of empathy for the aggravation caused by the October 2018 update.). As the speech was most likely vetted by PR and through their "infinite wisdom" probably thought not mentioning the issues was best. However as i said I would ideally need to see the speech it self to really comment about it.
  • From my perspective, Microsoft has a terrible problem with hiccups and chest pains with OS upgrades. It's _always_ been a problem for Microsoft (true for iPhone users too, but it seems to be a curse named Windows). The New Coke moment of Windows 8 was the true genesis of the Insider program. If Sarkar and Company are hyping their engagement with their customers and mega-incrementalism., then fine. But if she is talking about the great powers of telemetry and quality assurance, then she needs to take a giant helping of humble pie.
  • The devil is in the usage. The Insider programme is a fine idea, but it is useless unless the company reacts to the information reported back to it. As an example, Microsoft Edge is mostly unusable on Facebook. It will bog down such that typing any comment is like pulling teeth, whereas Firefox steams merrily along. When bluetooth goes wonky, the bluetooth controls disappear because W10 'thinks' it doesn't exist on the system, creating a Catch-22 scenario. Perhaps more staff is needed because it seems like we get features that sound like a fine idea but the damn things don't work as intended. If need be, do less things, but do them well. Doing many things not well is not a great corporate approach.
  • As has already been commented, the Insider Programs and the Feedback Hub are great achievements in the industry. The better question would have been what the quality would have been without it. I have been in the Fast Ring for years most of the time and only once I had an issue requiring me to do a fresh install. The missing files mishap for some is serious, but nothing at all to doubt the Insider Programs. To the contrary, another step has been made to improve them with introducing a severity scale with the feedback.
  • The insider program has always been a cheap way for Microsoft to outsource to people with no lives or too much free time that which used to be the work of paid workers.
    For that, they tell people their feedback "matters" and etc. Of course it doesn't. Windows Insiders have zero relevance in the development of Windows and none of their opinions matters when it doesn't match what Microsoft has internally already decided. Because of that, fewer and fewer people bother to actually report anything. And Microsoft sure as Hell doesn't bother paying too much attention to anything that isn't a major bug that affects a lot of insiders. The fiasco of the October Update, or as I like to call it, the Clinton Update, is a result of that silly idea that has been the Insider Program.
    Releasing software earlier to people might be nice but not in early stages of development. Things like Skip Ahead and Fast Ring shouldn't be open to people outside Microsoft. But that would require Microsoft to hire people to internally test software properly and that's expensive...
  • It's not expensive, not for Microsoft just not in keeping with the current fiscal policy. As long the stock price goes up, CEO get's softball questions. Simples. Let's not forget Ballmer and Gates own a fair amount stock too.
  • A lot of folks on the Fast/Slow ring are professionals... developers looking to mod their apps prior to major updates... IT shops looking to get a jump on what's coming to their users... and of course reviewers and bloggers sweeping the product with a fine-tooth comb. If Windows were a closed, straight-jacketed, proprietary OS that only ran on proprietary hardware (ie Apple) you could probably suffice two major rollouts a year with internal testing only. But you'd also be living in the weird... hey everybody look at me I'm just like everyone else... world of Apple. Windows, as you know, is meant to run on literally thousands of different configurations on thousands of devices made by a staggeringly wide variety of OEMs, supporting a huge army of both legacy and modern peripherals (cameras, scanners, printers, plotters, musical equipment, scientific equipment, etc. etc.). The Insiders program recognizes and honors that diversity... flexibility... and power... and is the perfect engine to allow them to pull off two major releases a year.
  • Dona Sarkar is surely in denial. The only reason that I can think of that might explain her advocacy of the insider program is that she wants other companies to join MS in the sewer. Was she appointed on Nadella's watch? Her commentary seems to come from the Nadella book of "100 ways to stuff up and look foolish". Let us not forget that she was a lead developer for the mighty Vista. It seems like you stuff up at MS and you get kicked upwards, a certain example of the Peter Principle.
  • Always move forward never backwards.
    and of course Learn from the mistakes.
    Also be fair the entire program has been a success
    over 7 million users is huge.
  • I ask the person who never ever makes a mistake to step forward and complain. The rest should remain silent in this case. It has been 1 flaw... 1. With thousands others succesfully fixed before the release. That is still a success. If we are to burn everyone over simply 1 mistake, then no-one would be alive. It's not like anyone died, it's just file deletion. Just put back your backup. If you don't have a backup, well... That's your problem. If this would happen every time with every update, sure, go ahead, flame and burn. Yet seriously just because of 1 bug that slipped through which effected not even 1 percent of the devices? Don't get me wrong, they SHOULD do everything in their power to prevent such bugs to slip through the net, yet let's please keep everything in perspective here.
  • I honestly think the October Update was exaggerated beyond what it should have. And to be using a bad update as a reason to downplay and hate on the Insiders Program is just ridiculous. The truth is the media will downplay anything having to do with Apple and piss on anything having to do with Microsoft or Android. For us to be still debating if Microsoft is bad for this mistake or not is evident of that.