Why Client Deployment is Such a Mess

I’ve been speaking to some folks about Windows 10 lately. I ask about it a lot at conferences, too. The general feeling, personally, is that about half the world is deploying, or gonna deploy. The other half, “meh.”

You know why the meh? Everyone probably wishes they had Windows 10 deployed, but almost nobody is excited about deploying it. It’s kind like me and “shoulders day” at the gym. Love having done it, not so hot on doing it. 

Close your eyes and go back to that happy, happy place and time, when your users all ran Windows 95. Then, Windows 98. Probably that was it. Lots of companies never broadly deployed Windows 2000 Workstation – it was a massive change over the MS-DOS based Windows versions, and they just weren’t up for it.

But along came Windows XP.

And it stayed. So not only most IT Ops people, but most entire companies, have only ever deployed a client OS maybe three times, max. Once, when you brought in Windows 95, which you probably did on new computers anyway. Again when you deployed Windows XP, and again when you finally rolled out Windows 7. Yes, lots of folks have done more, especially if you go way back, but the mass of the world seems to have done about two or three.

And it’s largely because deploying new client operating systems is a pain in the ass. It’s literally the most impactful thing IT can do to a company, because bloody everybody sees it. Everyone gets a new Start menu, a new Control Panel, and a new reason to bitch at us. Migrations never go 100% smoothly, because users stash stuff everywhere they’re not supposed to. Migration tools suck in large part because we don’t use them enough to generate any interest in fixing them.

And migrations are mainly a PITA because nobody has invested in building the skills, tools, or infrastructure to make it easy. Yes, Microsoft has released tools – lots of them, over and over – but none of them are a Magic Migration Deployment Wizard. Because migrations have always been this painful-point-in-time thing, we’ve never made it an ongoing process that requires us to make it a science. When we deploy OS v2, we don’t put in places the things to make the eventual OS v3 deployment easier. When we acquire client apps, we don’t bother even asking what the forward compatibility story will be.

And so client deployment is a mess.

Windows 10 might offer some relief. Maybe. It depends a lot on how long Microsoft follows through with this servicing branch theory they’ve got running, where most of our computers perhaps live int he Long-Term Servicing Branch (LTSB), but eventually suck down whatever updates are sent to that branch, while others can opt into a more-frequent series of updates as a means of testing new features and fixes. And if they stick with this as a means of shipping new features, eventually shifting to a subscription model rather than a one-time-sale model for client licenses. That’s a lot of “ifs” from a company that doesn’t have a great track record for sticking with update strategies (“we don’t ship new features in service packs,” lolz).

So either Microsoft takes this off our hands by making clients inherently “always upgrading,” without the need for backbreaking deployments and migrations, or we have to fix this ourselves. “Fixing” meaning actually building up the tools and processes so that if someone says, “yea verily, go thee and migrate the Sales department to Windows 12,” we can just nudge a button and have it happen. These damn client computers are our single biggest source of maintenance, upkeep, and security woes, and we need to be able to keep them updated – beyond just patching them.

Oh, also – I committed T-Mobile.

2 thoughts on “Why Client Deployment is Such a Mess

  1. Pingback: Why Client Deployment is Such a Mess | Skatterbrainz Blog

  2. BlondeBetty

    There are a lot of problems with Windows 10. I’m shipping new devices with Windows 10 and upgrading select devices currently and it has been an insanely rough road. The devices not going to Windows 10 will be moving to wmf 5. That deployment I’ve got in testing and should start rolling out in the next day or 2.

    It’s great that Microsoft has gone agile, except for certain parts of Microsoft. The windows desktop area of Microsoft was not ready for agile. I feel they have been forced into it and there are parts of it that are dragging their feet. You can see areas where they make and push changes, but either break, remove, or leave out a way to programmatically control those changes.

    I really feel like they are pushing towards removing most sysadmin control and giving all control to the end user. I’m still encountering certain group policies being overridden, defaults being removed, defaults claimed corrupt and removed, registry keys being ignored, settings reverting, and the list just goes on and on. These are all things that worked just fine in 7 and 8. I keep seeing IE lose its search engines, Home pages, and other apps losing their folder associations and windows claims they are corrupt or that they no longer allow those to be set by anyone but the end user.

    I still can’t figure out how Microsoft wants us to deploy and configure IE 11 settings. It’s a total cluster. You can’t follow what they recommend because even the stuff they posted at RTM seems to have changed our doesn’t work properly. There are just some settings it refuses to let you deploy.

    It’s hard to really ask others what their experiences are, because almost every person I know or communicate with haven’t even started testing windows 10 or attempted to even install it on anything other than their own machine. Some that I’ve talked to who have had blog posts on deploying it, couldn’t really help either, since they really only did the most basic deployment pretty much just got the blog post. You don’t really get into the meat of the issues until you really dive in and start trying to manage a desired configurations state for production.

    So, while I agree with many of your points, windows 10 is more than just an issue of not mastering our deployments. If they do not start strongly using their change log with great detail, a rolling and continuous upgrade could be even worse to maintain as a sysadmin. Now any update could change or break ways we manage our endpoints. Look at the 1511 update and the “consumer experience” setting. Before many would have had a chance to set or find out about that new setting, the damage is done. Candy crush, Twitter, and others would be installed and your users would be seeing ads in the start menu.

    I’ve invested far, far too many hours/days/weeks/months into troubleshooting issues and problems around deploying windows 10. I honestly can’t recommend any organization do it yet. There are just too many bugs and issues still.

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