Windows Copilot aims to be your best friend forever, but can you trust it?

Microsoft Copilot is more than just a tool–it’s designed to learn your preferences and tastes, and even anticipate your needs by buying stuff. Whew! That’s a big concept to try and get your head around. But that’s what Microsoft is trying to do, as it transitions to the next stages of its Copilot assistant.

We’ve used the term “assistant” rather loosely over the past few years. In part, that’s due to the aspirational marketing of companies like Google and its “Google Assistant,” which has provided answers to spoken questions and not much more. And we will tolerate those machines anticipating some of our preferences: autofilling commands, suggesting movies, and even automatically ordering refills as we run out of ink or milk. Knowing that we typically order orange chicken over chow mein? OK, fine.

Copilot wants to know all about you

Microsoft’s, um, thinking different. It wants to proactively offer you reminders and suggestions. How? By assigning a Copilot a “memory”: your nephew’s birthday and what gifts he might like, the foods you enjoy, and what movies you like. It all sounds very much like an advertising profile, and that’s probably what it is.

And if Microsoft’s Copilot starts to recognize you as a person, Microsoft hopes you might begin to think of Copilot as a unique individual, too.

“As we explore the full range of what true personalization means, we are experimenting with new ways for you to interact with your Copilot,” Microsoft said. “For example, what if your Copilot had an appearance and you could shape and form it to be whatever you want? We’re early in this thinking, but soon you’ll have the ability to personalize Copilot and interact with your AI companion in a fun way while it offers advice and support when you want it. You can strike up a conversation with Copilot and now have an entertaining appearance that’s unique to you.”

Creepy? Well, let’s put it this way: someone will use that term.

But there’s more. Microsoft would like Copilot to finally realize its agentic aspirations. Remember how ChatGPT was supposed to search out an open table at your favorite restaurant? Through partnerships with 1-800-Flowers.com, Booking.com, Expedia, Kayak, OpenTable, Priceline, Tripadvisor, Skyscanner, Viator, and Vrbo. Microsoft wants to make that a reality. Not only will it know what flowers your wife likes, but it could remember her birthday and order some, too.

“Use simple chat prompts to ask Copilot to book event tickets, grab dinner reservations, or send a thoughtful gift to a friend, and it will check that task off your list,” Microsoft said in a blog post.

It’s unclear, however, how much Microsoft will allow Copilot to actually make transactions on your behalf. In the demonstrations Microsoft showed, the user always made the final purchase. Whether that will end up being the case is anyone’s guess.

Microsoft does already have some shopping skills, however, since it has the ability to track prices and alert you during a key sale. Those sorts of agentic actions would be handy during the closing seconds of an eBay bidding war.

Is this Recall 2.0?

For some users, none of this will matter.

Microsoft took pains to reassure users that they could control which types of information Copilot remembers about them and even opt out entirely. But anyone who’s simply clicked and clicked and clicked again through the dozens of screens that make up the setup process in a Windows PC probably knows that it’s rather easy to simply hurriedly agree to Microsoft slurping up your personal data.

Those users will probably remember Recall, the Microsoft indexing tool that constantly snapped photos of your desktop before archiving them and allowing you to search the results. (Recall was revamped and then re-released for Copilot+ PCs.)

Even though Recall and the updated Copilot are two different things, some users are sure to see the updated Copilot as additional evidence of Microsoft trying to intrude in your privacy, once again.

“Every day we hear the most incredible stories about the many and varied ways people enjoy Copilot,” Mustafa Suleyman said. “So, as we continue on our journey to create a Copilot for everyone, we’re focusing on one critical goal: to make it truly yours. Each will have its own unique style and blend of attributes that distinctly suit each and every one of us. All the while, we’ll stick to our core promise. You remain in control; you are the pilot, and you make the calls and set the boundaries.”

That sounds promising, but your memory probably goes back a year or two when Microsoft debuted Bing Search, then Copilot, and weathered a firestorm of highly personable Microsoft chatbots doing strange things like inquiring about the status of a person’s marriage. Now Copilot is about as bland as it can be.

So can the new Copilot walk the line between a companionable assistant and one that tries just a little too hard to be your friend? History says no. But Microsoft sounds like it wants to take a shot at it. Hold on tight.