Welcome to Mossberg, a weekly commentary and reviews column on The Verge and Recode by veteran tech journalist Walt Mossberg, now an Executive Editor at The Verge and Editor at Large of Recode.

Welcome to Mossberg, a weekly commentary and reviews column on The Verge and Recode by veteran tech journalist Walt Mossberg, now an Executive Editor at The Verge and Editor at Large of Recode.

Fifteen years ago, when the time became ripe for post-PC devices that put a premium on integrating software and hardware, Apple was the best-positioned company to lead the charge — and it did. The company's vertical integration, its attention to detail and innovation in both software and hardware, and its willingness to make big bets gave it an edge. And it used that edge to reel off its now-familiar string of game-changing products like the iPod, the iPhone, the MacBook Air, and the iPad.

Now, the iPod is essentially gone, and the other products are in mature or maturing markets, with either pretty flat or dropping sales.

And the tech industry is turning to a new battlefield: artificial intelligence, spread across many devices.

After the success of Amazon's Echo, and the plans laid out at recent Facebook and — especially — Google developer conferences, it seems that the tech industry is pivoting in a big way to artificial intelligence and proactive assistance. Apple has some chops in this area, but it will be challenged to match what its rivals are promising.

The company's next opportunity to show what it has up its sleeve, if anything, will come at its annual Worldwide Developer Conference on June 13th in San Francisco. That's the equivalent of Google's event last week where AI took center stage.

Apple could have a very hard time in the AI war that's dawning

As I write this, I don't know what Apple will have to say when its turn comes to talk about the next versions of its software platforms. It may be mind-blowing, as Apple announcements have often been in the past.

It's also unfair to take Google and Facebook at their word that their voice-controlled AI and smart chatbots will be as great as they predict. After all, Google's current voice-controlled assistant isn't sensational, Facebook's is just starting, Amazon's is limited if growing, and Microsoft's recent attempt at a chatbot was hijacked by racists.

But Apple could have a very hard time in the AI war that's dawning — even though it actually pioneered the first widespread, voice-controlled, cloud-based AI assistant, Siri, on the iPhone 5 years ago and is now rumored to be bringing Siri to the Mac. (In fact, former Apple CEO John Sculley pushed an AI-powered conversational assistant concept called Knowledge Navigator, complete with concept videos, way back in 1987. It envisioned a conversational digital helper with abilities far beyond any that exist now.)

There are three reasons for my doubts: first, Apple's history with cloud-based services in general has been weak and inconsistent. Second, Apple has done shockingly little to capitalize on its lead with Siri. And third, Apple's steadfast devotion to privacy and lack of a search service or social network means it doesn't have the range and volume of data its competitors hope to use to power personalized, actionable AI capabilities.

Apple and the cloud: a match not made in heaven

As cloud-based services gradually grew in importance, Apple provided some of those to complement its devices, under a variety of sometimes confusing names, and with a mixed record of success.

It was early to syncing contacts and calendar items among your Apple devices. It could keep track, across devices, of songs you purchased in iTunes. Its iMessage and FaceTime services have been big hits, and have helped keep people in Apple's world. And, in Apple's biggest move of all, in 2011 it introduced the voice-controlled, artificial intelligence service called Siri as a feature of the iPhone.

Along the way, however, Apple also acquired a reputation for being generally weak in the scope and reliability of its online services.

Remember MobileMe? What about Ping?

Its MobileMe suite of cloud-based services was a famous flop and the name was dropped. So was its Ping music-centric social network. And the cloud and data based Apple Maps service, out since 2012, was the butt of jokes and is still inferior to Google Maps, even on the iPhone — though it's improving and is now more popular than Google's app on iOS.

iTunes Match and the iCloud Photo Library perform inconsistently, to say the least. The cloud-based Apple Music, which should have been a strength for the digital music titan, is a cluttered mess, and hard to figure out how to use. The most recent news around Apple's music service has been about users believing it deletes files, not about any of its artist exclusives.

Until recently, with the relatively obscure iCloud Drive, Apple even resisted offering a simple and common cloud-based virtual hard disk for storing documents, like Google Drive, Dropbox, or Microsoft's OneDrive. The result, I suspect, is that most Apple users don't rely on it.

Siri: when will you become smarter?

But perhaps the biggest disappointment among Apple's cloud-based services is the one it needs most today, right now: Siri. Before Apple bought it, Siri was on the road to being a robust digital assistant that could do many things, and integrate with many services — even though it was being built by a startup with limited funds and people.

After Apple bought Siri, the giant company seemed to treat it as a backwater, restricting it to doing only a few, slowly increasing number of tasks, like telling you the weather, sports scores, movie and restaurant listings, and controlling the device's functions. Its unhappy founders have left Apple to build a new AI service called Viv.

And, on too many occasions, Siri either gets things wrong, doesn't know the answer, or can't verbalize it. Instead, it shows you a web search result, even when you're not in a position to read it.

Siri isn't the type of natural-language helper the industry is aiming to build now

Last year, Apple added a Siri feature called "Proactive" — a sort of catch-up to Google Now, which shows recent apps, recent contacts, nearby retail services, and a few headlines. Proactive also remembers music you were in the middle of playing, suggests people to include in an email, and tries to identify phone numbers in email, among a few other things. But it isn't a full-bodied smart assistant or the type of natural language helper the industry is aiming to build now.

And, unlike Google's current voice assistant, Siri — at least in my experience — can't recall what you were talking about when you try to ask a followup question.

I'll be looking for Apple to show a greatly expanded Siri at WWDC in a couple of weeks, and to maybe even open it to third-party developers. In fact, there's a report that Apple plans to do just that, and is also working on a Siri-powered home speaker.

Unless Apple really does these things — and keeps doing more — I will regard Siri as one of the tech world's biggest wasted opportunities.

Do I know you?

If a company knows a lot about you, there's reason to worry that it's invading your privacy. But if a company knows too little about you, there's reason to question its ability to build highly useful artificial intelligence into its products.

Google and Facebook know — or can infer — a lot about you, from your favorite films to your age and family size to your job and hobbies. But because it is so wedded to privacy, Apple says it can't access your cloud-based information. It's so dedicated to privacy, in fact, that it has taken on the FBI over encryption.

At last year's WWDC, when it introduced Proactive, Apple made a big point of saying that it doesn't need to scoop up cloud-based data to make Siri smarter — it can just use what's local on the phone, with your OK.

Apple won't have the same kind of sources Google and Facebook have to draw upon

Maybe so. But I'm skeptical that Apple will be able to customize a chatbot or sophisticated Siri request with just what's locally stored on my phone. Already, most of my music, photos, and emails aren't stored locally. So that leaves Apple less to work with.

If I ask Facebook or Google to recommend a restaurant I'd like in, say, Milwaukee, with no further information, Google might know my tastes and price ranges from restaurant searches I did in another city. Facebook might know them from posts I liked or from what my close friends posted. Apple won't have those kinds of sources to draw upon.

Bottom Line

I'm rooting for Apple to succeed in this game, because more competition is better for everyone. But I have my doubts. So I'll be watching closely in 19 days to see what the company has to say about AI. You should, too.