Jay Little - Software Obsessionist
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Things I Don't Miss About Windows: Updates
3/12/18 11:45:48 PM

So I'm going to start off this post by being extremely blunt: I don't like Windows. In fact when it comes to Operating Systems (aka OSes), I consider virtually any other OS a superior choice. The only exception is situations in which some piece of critically required and irreplacable software mandates that you must use Windows. Despite these feelings and the fact that my house contains only two Windows machines, only one of which belongs to me (the other belongs to my current employer), I spent quite a few hours mucking about in Windows this past weekend.

How did this happen? Well it started with the fact that a few years back I was chomping at the bit to sign up for HBO's new streaming service called HBO Now. Nowadays that's not a big deal and users have a wide variety of options regarding where to sign up, what apps to use and most importantly: How to handle recurring subscription billing. However when the service was first unveiled in April of 2015, there was only one option for handling all of this: Apple iTunes. I already had an iTunes account, as I owned an Apple TV, so I used it to sign up. Now fast forward three years to this weekend when I realized that subscribing to HBO via Amazon Channels also grants access to actual live streams of the HBO channels rather than just on-demand content made available through the official HBO Now app.

So I needed to cancel my iTunes subscription. Guess what? You can only manage iTunes subscriptions via the iTunes application. And since I don't own a Macintosh, it was time to fire up the old freebie Surface 3 and install iTunes on Windows 10. I hadn't booted it up in over six months. I really had no idea what to expect. The first thing I got hit with were outdated browser warnings and outdated browser plugins, all of which are to be expected and easy enough to resolve. Once that was done, I proceeded to download iTunes for install. While it was downloading I decided to initiate the install of Windows Updates as I knew the machine was more than a little behind. In my world view, the only thing worse than dealing with a Windows machine is dealing with an outdated Windows machine. Missing a security patch in the Windows ecosystem can wreck insane consequences in a world full of malware that targets Windows users relentlessly.

So I kicked that off. iTunes finished downloading before the Windows Updates did which was hardly a shock. I launched the iTunes installer. It literally took 20 minutes to install, which was beyond silly. But hey it was a 250 megabyte installer for a piece of software that is basically just an overrated thin wrapper around a web site Apple refuses to let you access with an actual web browser, so I'm going to put that one on Apple's doorstep. Somewhere along the way Windows Updates began to install and this where things got really get hairy.

But before we go on, it's probably important to take a moment and relay just how insane all of this is to a Linux user like myself. While much of this experience is perfectly normal for a Windows user, for a Linux user this is all pretty horrifying. For starters I've literally described at least three seperate application update processes (in browser automatic updates, third party installers with their own auto update mechanisms and Windows Update itself). This is unheard of in the world of Linux. When I use my personal Linux laptop or log onto my Debian / Ubuntu Linux servers all of my updates are queried, downloaded and applied using a single utility and/or button click. It's unbelievably simple and most importantly: It's quick.

Now back to Windows. Needless to say this experience wasn't quick, though it was something short of insane. However if I was depending on this machine to do anything other than cancel an iTunes subscription or to program a Logitech Harmony One remote control, I would probably refer to the process as insane as I would be forced to go through it more often. Not only did I have to initiate the Windows Update process multiple times to counter the fact that the machine kept going to sleep (as I wasn't using it because I detest it) during the update process (which apparently cancels it), but each round of successfully installed updates simply led to yet another round of updates that needed to be installed.

While I'm sure somebody could offer a cogent technical explanation for why Windows Update is unable to offer you every available update out of the gate and install them all transparently (allowing for multiple automated rounds of installation if need be as I'm not completely heartless), this process was shit. It isn't friendly and frankly it doesn't really work all that well. Given how immensely important it is to keep a machine up to date with current patches from a security standpoint, it's absolutely silly that it took this kind of effort to get the machine somewhat up to date.

Yes, I just said somewhat. That's because this process is actually still playing out on my Surface 3. When I get a free moment and I think about it, I will go and check on it again. I'm always sure to check for more Windows Updates whenever it "finishes" as I want to be fully up to date before I shut the box down for another six months ya know. Regardless of my distaste for Windows, I pride myself on being a responsible netizen, no matter how painful it is to uphold those obligations at times.

Anyway it's time to go kick the Windows box again and see if it's done. Thankfully my Linux machines are still humming along fully updated within the span of mere minutes every month.

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