Ask Paul: March 10 (Premium)

Good morning and Happy Friday from Roma Norte, Mexico City! Here’s another great set of reader questions to kick off the week a bit early.
Realized ambitions?
sabertooth920 asks:

Roughly 20 years since Longhorn, do you think the various iterations of Windows (Vista, 7, 10, 11) have realized the ambitious aspirations Microsoft initially envisioned?  Obviously, much more gradually.

In an interesting coincidence, I just finished updating the Longhorn section in Windows Everywhere (which has grown to a mammoth 830+ pages with lots still to go), and I was literally just thinking about this. Not just in the context of Longhorn, but also of Cairo, which I wrote about the other day. These two projects very closely parallel each other in that each was ambitious and future-leaning, and of course each failed. The difference is that Longhorn did so publicly, whereas we’ve never seen a public build of Cairo to this day. (You’d think something might have leaked given how long it was in internal testing.)

I miss this Microsoft because they were really shooting for the stars. But the problem with evaluating them vs. what we have today in Windows is that the stakes are so much lower: when Cairo and Longhorn were ongoing concerns, Microsoft dominated personal computing, and everything that did---everything they said---had such weight. A simple announcement from this company could set the industry down a different path.

The influence of Windows faded slowly but it has only kept fading. The start of it, in some ways, was Mac OS X, which was so more advanced than Windows 2000 in some ways, but was also more advanced than Windows XP, which not only shipped later but was then kept in-market longer than expected because of the delays in Longhorn. That was the beginning of Microsoft ceding its technical leadership in the PC space.

Did Microsoft catch up? And to your point, did they realize their ambitions? Yes, mostly. But it’s interesting how many of the initiatives that began with Cairo/Longhorn just don’t matter much anymore.

For example, Cairo was supposed to introduce an object-oriented file system based on SQL Server technology and virtual folders, and the former was eventually found to be too top-heavy to be viable and was abandoned, as was a lesser attempt at a similar file system in WinFS. Virtual folders did happen in Windows Vista, and stuck around through Windows 7 (and are still technically available today, though you have to dig around to see that), but were found to be too confusing to users. That’s a great example of an engineering mindset running into the real-world needs of normal people. (Microsoft is apparently resurrecting ReFS for Windows 11; that file system debuted in the Windows 8 timeframe, but I believe it was only really used in Server. This won’t achieve the goals of Cairo/WinFS, but then I don’t think we really need any of that anyway.)

The biggest visual innovation in Longhorn was the Aero Glas...