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As we approach the "cliff-edge" of Windows 10 EoL in October I'm trying to get a very non-scientific straw-poll of how members' businesses are planning to meet this.
- Even if you have the benefit of Microsoft SA will you be entirely Win 11 by then?
- Does it remain a desirable target that you hope you'll achieve but might miss?
- Are you planning on a mix of operating systems being present with mitigations until you're able to move fully?
- Are you already costing ESU contracts to keep those Windows 10 non-security updates coming?
Previous "enforced" operating system upgrades have had a history of always leaving some behind, often because of bespoke software or hardware that's "mission critical" but also may not be compatible, it that happening where you are?
EE question threads don't really lend themselves to polls but looking to get a feel on how this is looking like rolling out?
If you're able can you give some idea of the number of licences your responses cover (do you have 20 machines or 20,000)? If you don't want your CTO seeing (or if you're actually the CTO!) you could always message!!
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@Daniel, that's really interesting, especially the Windows > Linux exit, what sort of sizes are these small businesses? Is there no interest in ESU uptake?
Your opinion.
If your company hasn't converted, it's due to lack of leadership push.
Wow, just wow. Not everything is black and white like you think it is. I'd love to see you in some of the organizations I support and decide if putting on a program for patients, or putting food on the table should be stopped to buy a new PC because Microsoft decided so. That's literally the choice in front of several of my clients.
There's also a huge difference between small/medium and big businesses!
I would never have setup my clients on Windows 11 when it first came out! Why would you put clients' through debugging software? It's nice having the new toys, but not in a business environment! In business you want stability. Setting business clients on the new MS OS or Office when it is first released is irresponsible of any serious IT professional.
I don't abandon my clients because they can't afford upgrades, or don't want to upgrade. I work with them as best I can. They know the risks and they assume them. I guide them as best I can, but I can't won't force them. They know about the Oct. deadline.
You might be amazed how hard it is for many small businesses and non-profit to afford buying a series of new PCs and affording the IT help in setting it all up.
Wasn't Windows 10 supposed to be the last OS?! That was short lived.
I think we've all views on the pros and cons of enforcing a minimum hardware standard but what I'm really asking for here is what is actually happening as the clock ticks down on Windows 10 EoL
While I agree that there's a leadership requirement (and this is coming from a 20k+ seat, public sector background) it's impossible to ignore the real world cost pressures on SMBs and there are far more of them dealing with their own priorities over this than the big corporates.
The question remains:
What is actually happening where you are?






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Wasn't Windows 10 supposed to be the last OS?! That was short lived.
Why would you believe that it would be forever. XP lasted 8 years for mainstream support and 13 years for extended support, from 2001-2014. Windows 7 lasted 6 years for mainstream support and 11 years for extended support and it kept getting additional extensions until 2023, so 14 years. Now Windows 10, has lasted 10 years There's still the ESU, so it'll stay for a few more years. You think Windows 11 will be around forever too? Apple's cycle is even shorter for most of their hardware.
This happen periodically since the start of the PC revolution. Why are people still not prepared? Why would you believe they'll never change versions. How do you think they make money? I have a bridge for sale…
When you buy a new laptop that only comes with Windows 11, you use Windows 11. Most businesses just use Office 365 ad Saleforce and other SAAS systems these days. Most of the companies I had maintained in my previous job had locked down computers with software published on Azure. They could not install anything that we didn't make available. Some companies even filter web browsing and need approval for access to pages. Users' systems are upgraded and should be upgraded. They had no choice in the matter.
Some were financial groups, some were clinical testing facilities a few were those small companies that we took over that wanted better support and better computers. We replaced their crappy OfficeMax/Staples computers with “Enterprise” computers mostly from Dell ad Lenovo. They cost more but come out to be about the same TCO since they'll last 3-5+ years instead of 1-2 with poorer performance specs. We know they were buying those cheap computers every 1-2 years because that's what they told us. All of those were heavily locked down to prevent user data leakage. If you're not properly calculating their TCO for the computers and show them real life performance and timelines, you're not doing your job. If you're in the USA, they're also not getting the full 5 years of property depreciation on those cheap junk.
Hospital equipment computers are a separate category and should not be connected to the internet. They're not user computers. User computers are upgraded. Medical equipment computers should be behind firewalls and limited from access to the internet in the first place. They're also not accessible to the rest of the users' computers. The clinical testing facility I worked with had those systems disconnected from other users and had special interfaces for access. None of those systems could connect to random internet sites. Those are special cases. They might stay on Windows 10 or even Windows 7 because they can't purchase new equipment. You had to deposit files into a safe transfer location that got separately scanned. It had patient data. The patient records were accessed through VMs and none of that data resided on user systems ever.
No.
Sticking with Windows 10 all the way.
Windows 10 is the new Windows 7.
Windows 7 was the new Windows XP
Windows XP was the new Windows NT/Windows 98

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All I have to do is watch all of the complaints/questions on this forum, and others, to know that Windows 11 is the new Yugo.
Time is money. Wasted time is lost money.
Ads are more wasted time as is bling.
People just want to freaking work.
Oh, and change. Yeah, it's Microsoft's machine not the company that actually paid for it. Kind of like GM saying, “you're driving on public roads so we're going to do what we want with the telemetry” and Adobe, “you're creating with our products so we're going to use your shit as we please”.
No opt-out. Hotel California baby.
Looks like the momentum for this has run out. Thanks for letting me know what's really happening with you.
We just had a sit down with our largest accounting firm in the region on this vary question.
The fear mongering is strong with Microsoft.
We talked about Windows 7 carrying the ball through successive horrible Windows versions and how Windows 10 is going to be the new Windows 7. We talked about the extended security updates as well.
But, the real discussion was around attack vectors because that's a part of Microsoft's marketing.
1: If the perp ain't in the perp ain't going to exploit anything. Train the human.
2: If a perp gets in because of an errant click by a human, then they're going to be focused on the product of the day: Windows 11. They won't waste time cycles on an OS that is no longer mainstream. This is a gimmee.
3: If there's a zero-day it won't matter what version of Windows whether Server or Desktop since there's shared code there.
It was a good conversation. They like the idea of not having to spend a lot of money on something pushed by guerilla marketing.






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Absolutely this!
Big fan of the first edition of the Immutable Laws, I guess a bit less so as #3 is much more wordy (and of course hosted by M$). Am genuinely fascinated by how this one pans out, particularly if M$ blink first.
https://learn.microsoft.com/en-us/security/zero-trust/ten-laws-of-security
I have a large banking institution (1 of the big five here in Canada) as a client and they still run PCs with WinXP as they require it for compatibility for some of their software. If a bank does this with all the in-house and external expertise guiding them, it does make you wonder!
Wow … that's a lot of FUD in that article.
“Security Theatre”
Yeah, that's how we sell SEP licenses today! (in 2005)

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We have Windows XP in production. Some older software requires it.
Security is always about layers.
The “Tiering” system today seems to be more about creating complicated environments that are difficult for the human to manage and thus keep secure.
KISS always wins. Tiering, not so much.
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This topic area includes legacy versions of Windows prior to Windows 2000: Windows 3/3.1, Windows 95 and Windows 98, plus any other Windows-related versions including Windows Mobile.