[talldayo]

Seems pretty clear, in hindsight. Microsoft won the enterprise "stack" by bringing Active Directory and the Office products to Mac. They were blatantly willing to go cross-platform, which meant Windows Server would be a sure choice for expanding companies that wanted to pay extra to ignore compatibility (and even then, neither MacOS Server nor Windows Server were that good of an idea).

So if Apple couldn't win the integrated product segment of the server market, they had to compete against the post-dotcom-bubble cloud behemoth. The one that had been more or less cannibalized by Linux and brought down to-cost or even below-cost by AWS. MacOS Server could carve out a cutesy niche as an accessible FTP server and Time Machine host, but they couldn't make a business out of it when Linux did it all for free.

[lukeh]

Mostly agree, but MS did not bring AD to the Mac: their server only runs on Windows, and the AD client was developed by Apple (as part of DirectoryServices/OpenDirectory, Heimdal and smbx).