Remember the days before Automatic Updates? For a long time, if you wanted updates to a Windows system you had to wait for a Service Pack or a new version. Once the Internet came around, you could download patches from Microsoft if you really needed them, but in general you had to wait for the new versions.
Then Microsoft introduced "Windows Update". You could go to the web site and it would scan your system and present you with a list of available updates. This worked for system patches as well as service packs, and was great for System Administrators and home users alike.
Both of these distribution methods worked well, and were characterized by one very important mode of operation -- they required the end user to take the action to install an update.
Then Microsoft introduced "Automatic Updates". Instead of users initiating the action, this system allowed Microsoft to initiate the action. Users and System Administrators raised objections, saying that this power would be too easy to abuse, and Microsoft's past track record of incompetence could put too many machines at risk. Microsoft responded by reassuring users that they would not force updates, and they would have a strict process in place to make sure they were fully tested before deployment.
Now that Automatic Updates has been in place for a few years, and while it's had success, it's had some recent and significant failures. Each of those failures puts the integrity of the entire system into question, and makes one wonder if the successes are only a result of careful stewardship by a few individuals, and not a bulletproof process that ensures the integrity of the updates. (For such a critical system, one cannot rely upon a "really good guy" to make sure the system works correctly -- there must be a rigid process in place to control releases.)
Some notable recent failures include:
Each of these failures calls into question not only the integrity of the Updates system, but also the integrity of Microsoft itself. Stealth updates and forcing new features on users is a serious breach of trust in the system, and is exactly the kind of thing everyone was worried about when Automatic Updates was first launched.
Because Windows is such widely installed product, no longer do these failures impact just the IT "back office", but every level of the organization. The fact that updates come monthly and almost always require a reboot is already weighing heavily on IT Managers ("How much downtime do I have every month because of Microsoft?"). Now IT Departments are faced with the additional burden of products being installed without their consent, and secret updates that don't even show up on the radar. The fact is that organizations are already looking for alternatives to Microsoft for many of their computing needs, much of which is driven by the constant headaches caused by the updates system.
Each of these failures, their relative frequency, and their impact on systems has shaken to the core the trust that we reluctantly gave to the system. We agreed to trust Microsoft because of their assurances, but every mistake introduced into Automatic Updates is another straw on that camel's back. With IT Managers getting fed up with Microsoft, and the increasing prominence of alternatives in the IT landscape, Microsoft better get its act together on Automatic Updates, or we'll reach the final straw sooner instead of later.