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In a normal month, you need a scorecard to keep track of Windows patches. Now, your scorecards need a scorecard. One ray of hope: It looks like some Windows 10 cumulative updates will include the new “Download and install now” feature.

The May 2019 Windows updates have taken so many twists and turns it’s hard to pin things down, but as of Thursday morning, here’s what we’ve seen.

Windows 10 cumulative updates

As of now, all of the recent versions of Win10 (1607/Server 2016, 1703, 1709, 1803, 1809/Server 2019) have had three cumulative updates in May. Depending on where you live (or, more correctly, which locality you’ve chosen for your machine), you’ve been pushed one or two of them. If you’re a “seeker” (and clicked “Check for updates” or downloaded and installed the patches), you’ve had at least two, and maybe three. Got that?

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You have to wonder who’s testing this stuff.

Admins, in particular, have had a tough month. April brought widespread breakdowns – bluescreens, hangs, very sluggish behavior – to hundreds of thousands of Win7 and 8.1 machines. This wasn’t a “small percentage” kind of event. For some companies, rebooting overnight on Tuesday brought seas of blue screens on Wednesday morning.

The first round of cumulative updates and Monthly Rollups arrived on Patch Tuesday, but the now-ubiquitous second round didn’t show up until late Thursday afternoon, two and a half weeks later. Talk about admins taking a beating.

We still have one Tuesday left this month – the mythical “E week” that Microsoft never talks about – so the month may yet end with both a bang and whimper.

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March was an unusually light patching month – all of Office only had one security patch – and there don’t appear to be any immediate patching worries. Just as in the past few months, Microsoft’s holding off on its second cumulative update for Windows 10 1809, raising hopes that it’s taking Win10 quality more seriously.

Win10 1809 deployment proceeded at a positively lethargic rate, even though Microsoft declared the OS fit for business consumption last week, leading to all sorts of speculation about the next-next update, Win10 version 1903, ultimately overtaking its younger sibling.

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Microsoft continues to hold Windows 10 version 1809 close to the chest. While all of the other Win10 versions have had their usual twice-a-month cumulative updates, the latest version of the last version of Windows, 1809, still sits in the Windows Insider Release Preview Ring.

For most people, that’s excellent news. It seems that Microsoft is willing to hold off until they get the bugs fixed, at least in the 1809 releases. May I hear a “hallelujah” from the chorus?

Mystery update bulldozer KB 4023057 hits the Catalog

You’ve heard me talk about KB 4023057 many times, most recently in January. It’s a mysterious patch that Microsoft calls an “update reliability improvement” whose sole reason for existence, as best I can tell, is to blast away any blocks your machine may have to keep the next version of Windows (in this case, Win10 1809) from installing on your machine.

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