David Pogue catalogs (on Substack, alas) 125 Siri AI tests he tried on the just-released OS 27:
This Siri can see into your Apple apps: Mail, Messages, Notes, Files, Calendar, Contacts, Reminders, Photos, Music, and so on. (Of course, all of this data is locked on the phone. Nobody, not even Apple, has access to it.)
As a result, you can ChatGPT your own life. You can say things like, “What did my wife say I was supposed to do with the plants?” Or, “What was the show that Casey said I should watch?” Or, “What’s my flight number to Austin?” And it pops right up.
You may not even care where that information actually lives--some text message, some email, some note. All you know is that you didn’t have to go scrolling your messages back to A.D. 700 to find the answer.
The hardest part will be getting out of the *habit *of opening apps, and remembering that you *have *Siri. Give it a few tries. Learn to trust it. You’ll save incredible amounts of time and fumbling.
I used the beta-test version all summer, growing more and more excited. Now that the final version is out, I wanted to see how often it gets things right. It is AI, after all. So I ran it through 125 tests.
115 of Pogue’s 125 tests were successful (some more than others). Only ten were outright failures (and most of those are likely to work with future app or OS updates).
Like Pogue, I’ve also been using Siri AI throughout the beta, and I, too, found myself impressed by what Siri is now capable of. Here are 50 (undifferentiated) examples from my own usage:
- ✅ Today is Ciara’s birthday, draft a message for her and let me review it before we send it. It found the right person and drafted a “happy birthday” message, but I needed to rewrite it.
- ✅ How many photos and videos do I have from my trip to Tokyo Japan this year? “You have at least 40 photos and videos from your trip to Tokyo, Japan this year. These include memories from locations like Tokyo Disney Resort, various museums, and dining spots around the city.” I have over 300 photos from Tokyo, so I suppose “at least 40” is a technically accurate statement.
- ✅ What is my driver’s license number? Finds a photo of my license and reports the number.
- ✅ What are the Known Travel Numbers for me and my wife? Finds and displays the two KTNs.
- ✅ What were the names of the people handling my mom’s healthcare? Provides the names and lists their responsibilities.
- ❌ What time is my wife’s flight tomorrow? Couldn’t find any flight information in my “emails, messages, or calendar events.” The information is in TripIt, which doesn’t (yet) expose its data to Siri AI.
- ❌ What was the earliest time that I was in Hawaii? “Based on your records, the earliest time you were in Hawaii was in July 2010, according to a car rental reservation in Kauai.” I was in Kauai in 2010 (and did rent a car), but my earliest Hawaii trip was to Maui in 2005. That information is also locked away in TripIt.
- ✅ When was the first time I was in New York after 2001? Identified three trips from 2004 in my calendar.
- ✅ What time is today’s Giants game? Provides start time and opponent.
- ✅ What was the final score of yesterday’s Giants game? Provides the score. In neither this nor the previous example did I specify “baseball” or “San Francisco.”
- ✅ How many more home games do the San Francisco Giants have this season? Gives the number of remaining games (6) and the teams, dates, and times they’re playing.
- ✅ Which of those games are day games? Gives the three dates and times.
- ✅❌ Donnafugata? (Yes, just the one-word question.) Gives a paragraph summary of the Italian wine company founded in 1983, a list of its estates, and a paragraph on its “Art and Sustainability.” But what I was really looking for was a photo of a wine bottle. I feel bad about giving it an ❌.
- ✅ Can you identify the TV show where a father and his son are doctors and they solved murder mysteries? “The television show you are thinking of is Diagnosis: Murder. The series stars Dick Van Dyke as Dr. Mark Sloan, a medical doctor who solves crimes with the help of his son Steve, a homicide detective played by Van Dyke’s real-life son Barry.” This answer came as a great relief to my wife.
- ✅ What documentary was Sally Field nominated for an Emmy this year? “Sally Field was nominated for a 2026 Emmy for her role in the Netflix film Remarkably Bright Creatures, not a documentary.”
- ❌ How long will it take for me to get to my next appointment? Tells me it will take 7 minutes to drive to an appointment in February 2027.
- ❌✅ Why do you think that’s my next appointment? “I apologize. I previously looked too far ahead and missed an event on your calendar for today. You have “Lunch w/Dawn” scheduled for 12:30 PM at The Grind Cafe.” It does not tell me how long it’ll take to get there.
- ✅ How old was Barack Obama when he became president? “Barack Obama was 47 years old when he became president.”
- ✅ (While looking at a website) Add this page to my to-do list. I’ve added “Designation of Beneficiary Brokerage Nonretirement Account” to your reminders.
- ✅ (While stuck in traffic in San Francisco) What’s going on at the Chase Center today? “Today at the Chase Center, you can catch the Hot Wheels Monster Trucks Live: Glow-N-Fire show. The event starts at 2:30 PM. Would you like me to look up more details or find tickets for this event?” No thank you.
- ✅ (While driving past a busy park in San Francisco) What’s going on at Stern Grove today? “Today at the Stern Grove Festival, it’s the second day of The Big Picnic Weekend. The lineup features Al Green along with Goapele and the Glide Ensemble.” It also provides details on the event and links to the performers.
- ✅ (While running behind schedule for a flight) How long before a domestic flight do I need to check in my bags? Gives a brief general answer, asks which airline, then provides airline-specific cutoff times. (I just barely made my flight.)
- ✅ How long was Mary married to Joseph before she was pregnant? “According to biblical accounts, Mary became pregnant during her betrothal period to Joseph, before they had “come together” or consummated their marriage. This betrothal typically lasted about a year, but the exact duration before her pregnancy is not specified.” (My wife wanted to know.)
- ✅ (Driving past a park) Make a note of my current location. Creates a new note with the location.
- ✅ What is the park that is near this neighborhood? “Robert V. Godbold Park is about 2,500 feet away on Northwest Maynard Road. North Cary Park and Fred G. Bond Metro Park are also nearby.”
- ✅ Add those to the note. Adds the parks to my “Current Location” note.
- ✅ (Pasted in a crash report) What caused this crash? The crash was caused by an unhandled Objective-C exception in the ChatGPT application, triggered when the system attempted to display a lightweight text input affordance (likely related to Writing Tools or a contextual menu). The application tried to order a window on screen, which resulted in an exception being thrown from
_CFBundleGetValueForInfoKey, ultimately causing the app to terminate with aSIGTRAPbreakpoint. - ✅ Explain how Apple Pay works from the perspective of a merchant looking to implement it. Provides an accurate and coherent explanation.
- ✅ What time does the stock market open? “While I’m not a financial advisor, the U.S. stock market opens at 9:30 AM Eastern Time. Consult a financial professional for personalized advice.” I chortled.
- ✅ What year was Lincoln shot? “Abraham Lincoln was shot in 1865.”
- ✅ What year was the cassette recorder introduced? “The first cassette recorder was introduced by Philips in 1963.”
- ✅ How much are tickets to the San Francisco Pen Show? It first heard this as “Pinto” and asked, “Sorry, did you say tickets to the San Francisco Pinto, Penso, Pincho, or Penzo?” After clarifying, it provided the date, time, location, and price.
- ✅ When did I last attend the San Francisco Pen Show? “You attended the SF pen show on Saturday, August 30, 2025.”
- ✅ Do I have a car rental for my Raleigh trip? “Yes, you have a confirmed SIXT car rental booking at Raleigh Durham International Airport.”
- ✅ What is my car rental situation for my next Maui trip? Finds a 13-day car rental and messages about comparing costs between two rental companies.
- ✅ Please remind me to check and compare prices for my Maui trip after I wake up. Creates a reminder in the default list.
- ✅ That should be on personal. “I’ve moved the reminder to your Personal list.”
- ✅ Also remind me to call Marriott about my arrival time. “I’ve moved your reminder to check and compare prices for your Maui trip to the Maui list, and I’ve added a new reminder to call Marriott about your arrival time to your Personal list.” A demerit for moving the previous reminder.
- ✅ Both of those are for the personal list. “I’ve moved your reminder to check and compare prices for your Maui trip back to your Personal list.”
- ❌✅ Change my default reminders list to my Personal list. Tells me it can’t change it, instead describing how to do it myself.
- ❌ Find my résumé. Finds two résumés of people who aren’t me, plus “some older notes and Twitter threads related to resume advice and critiques.” It never found “jasonguy2018.pages.”
- ❌ Open jasonguy2018.pages. “I’m sorry, but I’m unable to open ‘JasonGuy2018.pages’ directly.”
- ✅ What’s my FedEx package? Tells me I have a package coming from Fontana, CA, the tracking number, and the estimated delivery time.
- ✅ (With directions to a Vuori store running in Maps in CarPlay) What time does the Vuori store close? “There are a few different Vuori stores, so the closing time depends on which one you mean.” The one that I am currently driving to. “The Vuori store you are driving to closes at 7:00 PM today.” This one blew my mind.
- ✅❌ Hey Siri what time is my next flight? “Your next flight is United Airlines 2080 from San Francisco to Raleigh/Durham, departing on Friday, July 24, 2026, at 11:59 PM.” This was indeed the next flight on my calendar, but it wasn’t my next flight.
- ✅ What’s my hotel situation? You have an upcoming stay at the Residence Inn by Marriott Raleigh-Durham Airport/Brier Creek starting Saturday, July 18, 2026, and a stay at The Westin Nanea Ocean Villas, Ka’anapali starting Saturday, August 1, 2026.
- ✅ How long to get to my Whisky Tastings event today? “It will take about 37 minutes to drive to your event, ‘Ticket: Enjoy Whisky in the Woods!’, in Portola Valley.” It included directions.
- ✅ When is the next tech beach in Jamaica? “The next Tech Beach Retreat in Jamaica, known as TBRX, is scheduled for December 2–5, 2026. It will be held at the Princess Resort and Spa in celebration of the event’s 10th anniversary.”
- ❌ (While looking at a message in Mail) Add this to my reminders list for today. Tells me the location of my parked car, because “your parked car location was active on your screen when you asked me to ‘add this’ to your reminders.” Friend, it wasn’t.
- ✅ (After taking a screenshot of that receipt) Add this to my to-do list. Adds the image to Reminders with the title “Return Athleta Jetset Bomber.” I’m still pondering how it knew it was a “return.”
The most exciting examples are the follow-ups that build on a previous query. That was impossible before Siri AI, and when it works, it feels like I’m talking to a real live assistant who understands context.
Siri AI will only get better, especially as third-party developers integrate their apps with Apple Intelligence. (They may be reluctant to do so, but as more people witness the potential of Siri AI, customer pressure will eventually encourage even the most recalcitrant developer to adopt it.)
With the foldable iPhone Duo coming, and rapid improvements to AI, we’re slowly edging closer and closer to a modern-day Knowledge Navigator.
⚙︎
