November 21, 1985: Following Steve Jobs’ departure, Apple comes close to signing its own death warrant by licensing the Macintosh’s look and feel to Microsoft.

The deal, between Microsoft co-founder Bill Gates and Apple CEO John Sculley, comes hot on the heels of the Windows operating system’s release. The pact gives Microsoft a “non-exclusive, worldwide, royalty-free, perpetual, nontransferable license to use [parts of the Mac technology] in present and future software programs, and to license them to and through third parties for use in their software programs.”

Oh, boy!

Craig Federighi, Apple’s senior vice president of software engineering, says Macs with the new M1 processor could run the version of Windows Microsoft created to run on similar chips. Apple did nothing to make that impossible. So whether Apple Silicon Macs ever run Windows depends on Microsoft.

November 10, 1983: Microsoft tells the world about an upcoming product called Windows, which will bring the graphical user interface to IBM PCs. Although Microsoft’s announcement about the new operating system comes before Apple launches the Mac in 1984, Windows 1.0 won’t actually ship until November 1985, earning it a reputation as “vaporware.”

At the time, Apple doesn’t view Windows as much of a threat. That doesn’t take long to change, however.

November 6, 2003: After porting iTunes to Windows, Apple sets a new record for digital music sales: a massive 1.5 million downloads in one week.

Bringing iTunes to PC users opens up a new, lucrative market for Apple. The record-breaking sales clock in at five times more than the 300,000 downloads Napster (remember it?) achieved in its debut week. And 1.5 million is double the 600,000 iTunes downloads per week Apple reported selling to Mac users prior to the Windows release.

October 16, 2003: Six months after opening the iTunes Music Store for Mac owners, Apple expands the service to cover Windows PCs as well.

Steve Jobs later quips that making iTunes available to Windows owners is akin to “giving a glass of ice water to somebody in hell.”

August 14, 1991: As Apple and Microsoft head to court to battle each other, the tide begins to turn against Cupertino and its claims that Windows unlawfully copies the look and feel of Mac OS.

The case concerns whether key elements of Apple’s operating system are original enough for copyright protection. The decision turns out to be a major blow against Apple — and the start of the company’s 1990s decline.

Parallels Desktop 16 for Mac launched Tuesday, bringing new features and performance enhancements that mean the virtualization software delivers the “ultimate Windows-on-Mac experience,” the company said.

The update also preps the popular software for the upcoming release of macOS Big Sur. That required a major effort from Parallels’ engineers.

“We had to re-engineer all of the (kernel extensions) that we would need from scratch to work with the new macOS kext that’s integrated into the product,” said John Uppendahl, Parallels’ VP of global communications, during an online briefing about the software. “And to give you context, that alone took 25 man-years of engineering work.”

Apple has confirmed that Boot Camp, the tool that allows Mac users to boot into Windows, will not be available on upcoming machines powered by custom ARM chips. Users will need to rely on virtualization software instead.

June 11, 2007: At WWDC, Steve Jobs unveils Safari 3 for Windows, bringing its web browser to non-Apple computers for the first time.

Apple advertises Safari as the world’s fastest and easiest-to-use web browser, capable of rendering web pages up to twice as fast as Internet Explorer and 1.6 times faster than Firefox. It lasts until 2012, but never becomes a major player on Windows.

If you really have to associate with Windows users, there might come a time when you need to send them a Pages document they’ll want to open in Microsoft Word. Here’s how to ensure your file is Word-friendly.