“Once burned, twice shy.” That’s good advice if you’re working around a hot stove. It’s an equally wise strategy for anyone responsible for administering Windows 10 PCs.
After the disastrous rollout of Windows 10 version 1809, you should indeed be extremely wary of touching that hot stove. Microsoft had grown cocky after a handful of relatively trouble-free feature updates to Windows 10, and had even bragged about how quickly it was able to roll out those semi-annual feature updates. That hubris caught up with them in late 2018.
Only days after rolling out version 1809 to the public, a pair of data-destroying bugs forced the company to pull the update from its servers. It took more than five weeks before the update was relaunched.
That painful experience inspired Microsoft to rethink its enthusiasm for those every-six-months updates. In the wake of the version 1809 debacle, the company promised major changes in the way it tracks product release, including a renewed focus on product quality.
One of those major changes was a deliberate slowing down of the rollout process for the next feature update. Microsoft’s engineering team signed off on the 1903 release, build 18362, in mid-March 2019. Under the previously established norms, that release would have gone to the general public beginning in April. That’s not happening this time around.
Because of the slower rollout process, what would previously have been an April update is now officially the May 2019 Update for Windows 10 (version 1903). And as we approach the end of May, that update is still undergoing testing by members of the Windows Insider Program as well as corporate customers and developers who have access to early releases of Windows 10.
For now, if you want to upgrade a Windows 10 PC to version 1903, you’ll need to use one of the following techniques:
- Assign the device to the Windows Insider Program, choose the Slow or Release Preview channel, and use Windows Update to install the new version.
- Download the version 1903 installer files from an official Microsoft source (such as a Visual Studio subscription) and run the Setup program, choosing the option to keep existing programs and files.
When you try either technique, there’s a good chance you’ll encounter the following error message:
That generic message is misleading. Even if all your hardware is fully compatible with Windows 10, you’ll be blocked from upgrading if any external storage devices, including USB flash drives and SD cards, are attached to the PC you’re trying to upgrade. You might also encounter this upgrade block if you’re using a PC with two or more internal hard drives or SSDs.
The issue is documented in this Microsoft Knowledge Base article: “‘This PC can’t be upgraded to Windows 10’ error on a computer that has a USB device or SD card attached.”
The bug in question causes drive letters for secondary drives to be reassigned during Windows 10 Setup, which can wreak havoc with system functionality, including backup programs. Microsoft says the issue “will be resolved in a future servicing update for Windows 10.” As a workaround, you can physically remove the USB flash drives or SD cards until Setup is complete.
That’s not the only issue associated with version 1903, of course. As of May 20, the status page for build 18362 has been updated 11 times since its initial release in mid-March, and it still lists three upgrade blocks. In addition to the issue associated with external storage devices, your PC will be blocked from upgrading if you have older versions of games with anti-cheat software that can cause crashes. There’s also an outstanding issue that affects machines with known folders (Desktop, Documents, and Pictures, for example); Microsoft says the issue does not cause any files to be deleted, and engineers are working on a fix.
If all goes as expected, Microsoft will release a servicing stack update for previous versions of Windows 10 shortly. (You can download the current servicing stack update for your edition from this page: “Latest Servicing Stack Updates.”) That should be followed by the general release of version 1903 to a subset of the Windows 10 installed base.
One of the post-1809 commitments from Microsoft was a dashboard for monitoring the health and stability of each new Windows 10 release. That Windows Release Informationdashboard is now live. It contains just about everything you need to know for currently released Windows 10 versions, with dates for when they were made available for their respective servicing channels and their end-of-support dates.
When version 1903 is released to the general public, its details will be added to this list, under the Semi-Annual Channel (Targeted) servicing option. Using the links on the left side of that page, you’ll be able to track known issues, including the status of upgrade blocks. But in another major change to the Windows 10 release model, this feature update won’t be installed automatically via Windows Update; instead, it will be offered as a separate update, and you’ll need to manually download and install it. (Feature updates will be delivered automatically when the current version reaches its end-of-support date.)
Even after the version 1903 update begins its slow public rollout, I recommend caution. You can monitor that release health dashboard to identify bugs that might affect PCs you manage. For business customers, consider waiting until Microsoft has declared version 1903 ready for widespread deployment. When that happens, you’ll see a new line on the dashboard for the Semi-Annual Channel servicing option.
And even that milestone doesn’t mean you need to rush into an update. Consumers and small businesses have 18 months from the release of a feature update before they’re required to install an update. On machines running Enterprise or Education editions, you have up to 30 months of support for the current version. Assuming the PCs you manage are running version version 1803 or later, you have at least six months to test version 1903 before you have to begin making upgrade plans.