The not so brave new world of Windows 10 updates.

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Much as Microsoft would like us to believe it, the continuous and seamless delivery of a Windows OS still isn't a reality.

I had been happily using my Windows 10 Dell XPS 13 2-in-1 laptop for the last couple of years without any issues. However, my version of Win 10, Version 1803, was reaching its end of life, so I decided to update it.

To cut a long story short; I spent two days without my laptop as we attempted numerous upgrade attempts; culminating in a total rebuild and re-installation of all my apps.

Where did it all go wrong?

I had ensured that my current version was fully updated using Windows Update, in addition I had updated all my Dell XPS laptop drivers. 

I then used the Windows 10 Update Assistant tool to download and run the upgrade process. I left the office at 6 pm with the machine running at 94% install progress; feeling confident that it would be completed in time for my 8 am online meeting the following morning.

I arrived at 6:45 am to find the machine at 99% complete. That’s right, 13 hours to get from 94% to 99%, a fairly clear indicator that the upgrade process had stalled.

Googling “Windows 10 Upgrade Assistant Stuck at 99%” highlighted the following known issue and workaround from Microsoft (https://support.microsoft.com/en-gb/help/4027554/windows-windows-10-upgrade-assistant-is-stuck-at-99)

I followed the instructions, until I reached step 6 where rather unhelpfully the screen wasn’t referenced correctly – it isn’t entitled the “Get Important updates” screen. However, I spotted this and managed to complete the steps successfully, et voila! – my XPS finally loads with Win 10 1909 and I logged in.

A blue screen awaits.

I was thinking now that I had gone to all this effort, I might as well make sure all my Windows Updates are up to date. So, I let Windows Updates do its thing and then restarted in order to finish the installation of the updates it had downloaded. End result – blue screen on start up!

Several restarts later, same result each time – blue screen. I booted up in safe mode with networking, but no networking available. Attempted various other repair steps but ran into the same problem every time, as they all needed a local admin account and I stupidly hadn’t created one. In my defence, on setting up Windows 10, Microsoft encourages you not to! Do not heed this advice is my advice, and always set up a local admin account.

Long story short, nothing could be done apart from wiping the device and reinstalling Windows from scratch.

While all this time my colleagues worked away happily on our thin client/Citrix platform that we can update in a matter of minutes for all our users.

The implications.

This personal experience got me thinking about the implications for our business as a Managed Service Provider (MSP) and for the customer networks that we look after.

1. My experience raises the following questions: What happens to customers who are thinking of ditching their virtual desktop environments for thick clients? I ask this as I recently came across an organisation that is equipping nearly a thousand end users with laptops and I really don’t think they have thought through the implications. Their IT team has been ignored, and they have nothing like the resource to handle the flood of support calls and additional maintenance it is going to demand, let alone the health, safety and security issues that working on laptops brings with them.

2. Did I do something wrong? Had I made a simple task difficult?  My subsequent research and consultations with colleagues show that I didn’t. One thing is for sure, the dream of seamless OS upgrades with Windows is still not a reality.

3. Can we automate this process intelligently in our role as an MSP? Do the tools exist to handle large scale desktop Windows 10 feature upgrades without creating significant downtime risks and harming customer satisfaction? The answer I am told is no, or rather those that do exist but are very poor. So, when the upgrade process fails there is a need for manual intervention and potentially significant intervention, which for large scale fleets is a real challenge.

4. What is the impact on stretched IT service teams and MSPs? I think Microsoft have presented us all with a huge headache. The feature updates all refer to Windows 10 which our customers see as the same product, but under the covers we know these feature versions can be very different. The problem is our customers don’t see it. They understood the nature of the change when we talked about the move from XP to Windows 7, or Windows 7 to Windows 10, but now they are in danger of being sold a dream that isn’t a reality – the continuous and seamless delivery of a Windows OS. 

This is all costing MSPs and internal IT teams dearly. Previously, customers understood that upgrading to a new OS was a big deal that required resources and was therefore chargeable so required a budget to be allocated for the work required. On the face of it, Windows 10 feature upgrades appear less critical. As a result, it’s a lot more challenging to make clear their implications and the potential disruption, yet the effort required to install them is just the same.

Needless to say, I won’t be recommending large user bases ditch their VDI platforms anytime soon.

For information about Quadris’ future-focused IT solutions, contact Gavin Young on 0161 537 4980 or gavin.young@quadris.co.uk