Ever since Windows 10 2004, the May 2020 feature update, began rolling out, I’ve been pestering Microsoft about the number of late-breaking incompatibility issues the company disclosed only after the rollout began. And every time I ask, I get the usual “we have nothing more to share” answer. So I tried going the sources route to find out what’s happening and what Microsoft intends to do to make the Windows 10 feature update rollout process smoother going forward.

Sources inside the company who asked not to be named acknowledged there’s been mounting pressure from the inside to figure this problem out. Yay! I’m glad to hear it’s not a case of “everything is fine — nothing to see here.”

Microsoft began rolling out Windows 10 2004 to “seekers” on May 27, 2020. This was after months and months of testing with Insiders and numerous cumulative updates applied to the “final” version of the update. But one day later, on May 28, Microsoft posted a number of blocking issues for Windows 10 2004 that had not been disclosed during Insider testing. The Always On/Always Connected blocking issue affected Surface Pro 7, Surface Laptop 3 and other Surface devices (though Microsoft never actually called out these devices specifically as being blocked by this) — a problem not remedied until July 1. It still took me two more weeks to have Windows 10 2004 “offered” to my Surface Laptop 3 via Windows Update.

We Surface paying customers, not to mention Microsoft’s own employees and execs, unsurprisingly aren’t keen on hearing our own premium Surface devices can’t get an update, when one would think Surfaces would be at the very top of the list of tested devices. (Were they this time around? I couldn’t get a firm answer on that from folks I talked to.) 

There have been some inside the company who think Microsoft’s decision to provide a regularly updated Windows Information Release dashboard page, listing some of the bigger known compatibility issues, is a mistake, erring on the side of too much transparency.

But I’m hearing the servicing team is pushing forward and intends to keep the updated dashboard around in spite of pockets of opposition. It also is stepping up work around drivers, which have proven to be a big blocker for Windows 10 2004 and some previous feature updates. Problems with NVIDIA, Realtek, Conexant and Synaptics audio and other drivers have all affected the rollout of 2004. Sources say need Microsoft is working on beefing up the driver test matrix by adding more hardware/driver combinations and coupling that with their artifical intelligence/machine learning tech to highlight potential problem areas before and after rollouts begin.

Speaking of the “after” rollout period, Microsoft also is working to do what many Windows users have been requesting: Make blocking issues clearer and more customized. Microsoft’s goal is to provide Windows 10 users with much more specific information on why their machines are blocked from receiving a particular update and to give them an inbox notification that is both specific and actionable, I hear. None of my contacts would say when something like this might happen, unfortunately, but at least it’s on the list.

I pressed my contacts for information about how well/poorly Windows 10 2004 is faring, blockage- and problem-wise, compared to other Windows 10 feature updates. It sure seems from anecdotal, Twitter and email questions that I and others have gotten that the 2004 rollout has been more problematic on this front than some but maybe not all feature updates. All my contacts would say is Windows 10 2004 is doing no worse than previous updates in terms of rollout pace and blocks that Microsoft had to put in place. If this is true, my guess is the reason we’re seeing more stories and blog posts on 2004 problems is — at least in some part — because Microsoft is telling us via its dashboard about some of the blocking issues, making it easier for all of us to write about them. And Twitter definitely makes it easier for all of us to kvetch about our problems.

I will note there are a bunch of blockers and problems with Windows 10 feature updates that never get mentioned on the Release Information Management known issues page. I, myself, had an Ethernet driver problem that surfaced when I moved to 2004. After many hours, I figured out updating my DisplayLink Ethernet driver for my Dell Universal dock seemed to do the trick and made my Ethernet driver reappear in 2004. Another example: A number of users are reporting domain-profile issues after upgrading to 2004. When I asked Microsoft about this one, a spokesperson said the company was aware of the issue and working on a fix, but had no timeframe as to when it might be available.

I understand it’s not possible to test every possible Windows PC, driver and peripheral combination for every new feature rollout — especially when a number of the PCs slated to get the update are five ore more years old. And maybe, if the rumors are true, Microsoft will be moving to just one Windows 10 feature update per year starting next year. (Officials haven’t confirmed my report that they’ll be doing a Windows 10 feature update in H2 and a Windows 10X feature update in H1, going forward, which would give Windows 10 feature updates even more time in the oven before rollout.)

I asked Microsoft again this week for an official statement on what’s been happening with Windows 10 2004’s rollout and blockers, but was told yet again the company had nothing to say.