[jimnotgym]

I wonder start makes your setup so fragile? We have a similar number of Windows machines, and we would be doing nothing in IT this week if we were just answering support calls.

We use WSUS for updates, and barely have to touch it?

Again I don't have any problem with licensing. I tell a reseller what I want and review their response. No big deal?

[krylon]

> We use WSUS for updates

So do we. But I have encountered my fair share of cases where an update to Windows or Office broke some third-party application. Once, and update for Office 2007 failed to register properly (but only on two machines), so after the reboot, Windows Update wanted to install that update again, followed by a reboot, etc. Once, an update to Office broke Autodesk Inventor, and reinstalling inventor subsequently broke Outlook. And don't get me started on Siemens SIMATIC/WinCC software. I have seen Office 2013 cease working spontaneously (again, only on a few select machines, and only a full reinstall fixed the issue), I have seen a certain revision of the AV software we use cause Windows 8.1 to crash regularly (literally: every 24 hours, the same time of day).

During my training at a large IT company, I heard they had a team whose entire job was to install and test updates to Windows and third-party applications and test if they broke something. I used to think they were a bunch a wimps, but after a couple of years as a Windows admin, I envy them for having the resources to do that kind of testing. My strategy is to wait for a couple of days after updates become available, check a couple of forums if anybody complains about stuff breaking and then release the updates that I consider safe.

> I tell a reseller what I want and review their response. No big deal?

Have you ever had to deal with, say, per-CPU vs. per-user licensing for SQL Server? Or consider whether to use a plain old license vs. software assurance? Maybe using GNU/Linux or BSD on my private machines has spoiled me, but I always wonder if MS wants to annoy their customers or if they just want to screw them over.

I am not sure if we are doing something wrong or if you are lucky. But I am glad that I do more programming than sysadmin tasks these days.

[jimnotgym]

> Windows 8.1 to crash regularly

When windows 8.1 came out, we stayed on Windows 7. When Windows 10 came out, we stayed on Windows 7. We downgraded each new machine to Windows 7. Last year we gave a power user Windows 10 to find out how it operated with our collection of third party software. Two more were added over the year. A year later we are rolling out Windows 10 across the estate. I think this is the answer, we run a conservative strategy with regards to OS versions. We went from XP, to 7 and then to 10 and skipped all of the experimental versions. don't get me wrong, I tried them all, I installed Windows 10 on my laptop the day it was available, but not on my domain...no way.

We let WSUS install critical updates when it wants to. I don't install much else without a good reason. AV updates have caused a few freezes that have meant a couple of reboots are in order, but not much else.

I use Kubuntu and Ubuntu server and I have had some really annoying update issues with them too. I used to have an Apple laptop that after updates would disable it's own wifi and need a reboot.

> Have you ever had to deal with, say, per-CPU vs. per-user licensing for SQL Server?

No, but if I did it would be licensed once and then stay the same for years. I do have Oracle, like you mentioned before. That has a very quirky license, but that hasn't left me anything to do for 3 years since it moved server. It did 7 years on the old server!

I think one of the secrets of enterprise IT is conservative versioning, "n-1 is the version you want", I was told some years ago. A normal PC at our place would be running Windows 7, ERP client, browsers, and Office 2010. A number run Adobe cc and other things I can't avoid. We are looking at moving to Office 365, but if we instead re-buy Office 2016 we will stick with it for years. Perhaps that is the secret? It seems like you are unable to run this conservatively in your environment?