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.

Apple is working with Microsoft to make new Xbox Series X controllers compatible with iPhone, iPad, Mac and more.

Support for Xbox One, PlayStation 4 and other controllers is already baked into the latest versions of iOS. It’s not yet clear if Apple will add support for the PlayStation 5’s new DualSense controller, too.

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.

Microsoft is reportedly using a workaround to get Xbox Game Pass on iPhone and iPad. Rather than going into the App Store, this cloud-gaming service will be available as a web application.

This is the same strategy Amazon took to get its own streaming game service on Apple handsets and tablets.

It’s been a hot minute since Microsoft and Apple were the big tech rivalry. But Microsoft is ready to renew cold war hostilities for old time’s sake. At least, if a new blog post is to be believed, that is.

In a new blog post promoting the Microsoft Store on Windows 10, Microsoft takes a few thinly veiled shots at Apple, cashing in on the current rough time Apple is having regarding its allegedly monopolistic running of the App Store.

Microsoft is working on a major Outlook redesign inspired by macOS Big Sur. Its new app, which is redesigned from the group up and promises to deliver a reimagined email experience, will land in October.

September 11, 2009: Microsoft CEO Steve Ballmer reportedly snatches an iPhone from a Microsoft employee during a meeting and pretends to destroy it.

This isn’t the first time Ballmer behaves in a wacky way and incurs negative publicity as a result. However, it’s an embarrassing moment for a man who ranks among the world’s most powerful people.