When I copied files from Google Drive to the Files app on my MacBook (and in iCloud), I spent hours (days?) renaming files. A file named 0002346.pdf tells you nothing… you have to open the file. The new OS (both MacBook and iPhone) makes this a snap. (Clip is only 24 seconds and has no audio)

It’s been a few years since I decided to move key elements of my online life from Google to Apple. I still have files in Google Drive and Google Docs but most of those are also in my Files app on my devices and in iCloud. As I recall, I wanted to have anything of importance in the Apple ecosystem.

With the arrival of the news and improved Siri AI, that has started to pay off. It’s early days but I’m impressed by what I’ve seen so far. Exhibit A: my Calendar app.

I spent hours entering every event (of any importance) in my Day-Timer’s to the Calendar app on my MacBook (The Great Calendar Project). Even attaching relevant PDFs when I had them. Don’t ask me why. Probably the same reason I’ve maintained this blog for 25 years. Siri AI now gives me a handy (fun?) new way to tap into this archive.

Pretty sure this is not what the Apple programmers had in mind as they worked on Siri AI. Most folks just want to know what’s coming up.

In the coming days and weeks I look forward to exploring what Siri AI can do with all of the data I have (obsessively) collected in various apps.

I’ve been playing with the new Siri AI and find myself more impressed with every little experiment. I think Apple finally got this right. In a recent Substack article (“125 Tests of the New AI Siri”), David Pogue calls it “a phone-changer.” (That will make more sense after you play with it a little)

It replaces most Google searches, most ChatGPT or Claude interactions, and cumulative hours of fumbling and searching and dragging and copying and finding and tapping and pasting. […] You can ChatGPT your own life […] The hardest part will be getting out of the habit of opening apps, and remembering that you have Siri.

It’s tempting to tell those around you, “Wow! Did you know Siri can…” but I’m going to resist that temptation. Here’s the thing… Android users (who all secretly suffer from Apple envy) will insist their phones have done xyz since the early 70s. The anti-AI crowd simply doesn’t want to hear about… anything AI related. So I’ll try to limit myself to sharing WHOA! moments here. Continue reading →

(Perplexity) Apple executives have explicitly stated that the new Siri AI is intentionally designed to avoid the engagement-driven and relationship-building models used by competing chatbots.

In public remarks, Craig Federighi, Apple’s Senior Vice President of Software Engineering, contrasted Apple’s philosophy with the rest of the industry by criticizing the focus on user engagement:

“If you use many of the existing chatbots, they’re really focused on engagement to a large degree. And sycophancy, right? They kind of want to pull you in. They might encourage you to reveal things about yourself, and then use that as a basis to establish a connection.”

Federighi further clarified that Siri’s design architecture purposefully rejects this approach:

“The way that we have designed Siri, Siri really wants to say ‘Listen, that’s not what I’m here for, right? I’m here to help you. I can help you get things done. I can help you learn about the world.’ But if you try to engage Siri as a romantic partner, Siri’s not up for that.”

Key Elements of Apple’s Approach

•  Utility Over Companionship: The system is built around direct, task-focused interactions—such as on-screen awareness, searching deep within personal messages, and executing multi-step app automations—rather than prolonged, open-ended conversations designed to maximize session time.
• Rejection of Personification: Testing of the updated Siri confirms it is programmed to decline “acting human” or expressing personal feelings, preferences, or favorites.
• Privacy Alignment: Minimizing conversational engagement reduces the intake of unnecessary personal data, aligning with Apple’s reliance on on-device processing and Private Cloud Compute.

I think this is exactly the right strategy and can’t wait to try out Siri AI. Readers of this blog might remember I was a big fan of ChatGPT. I deleted my account a while back for a couple of reasons.

OpenAI had been making noises about advertising and while I never saw an overt ad, I can’t be sure it wasn’t happening under the covers. Basically, I just didn’t trust the company or Sam Altman.

And I could not get ChatGPT to stop smooching my bottom (“Great question, Steve!”) Updated my settings but the model was trained to encourage engagement to keep me coming back. Ewww!