In general, technology gets smarter over time. New features are added that improve the functionality, or changes are made that allow a device or app to do the same thing in smarter ways.

But every now and then, a new feature can effectively end up making an app dumber – and Apple’s Calendar app is guilty of this …

I’ve hit a couple of examples.

Proactive assistant

First, when Apple introduced the Proactive assistant in El Capitan and iOS 9, that should in theory have made life easier for us. One of the things it does is scan our emails from a list of companies like airlines, hotels, restaurants and so on, looking for booking details.

If it finds one, it proactively adds that to our calendar, informing us that the appointment was ‘found in email.’

Which is great – except when we already added the event manually. Then we end up with two events, one of which we have to delete. What should be a time-saving feature actually ends up wasting our time. Even on iOS, where Proactive displays a banner and asks us to choose whether or not to accept it, it’s an extra step.

A classic example are hotel bookings. I add these to my calendar when I book them, and the confirmation email doesn’t arrive until sometime later. By the time Proactive adds it, it ends up duplicating what is already there.

Of course, there are a couple of workarounds. We can turn off the feature, or we could just trust proactive assistant to do its stuff and refrain from adding these events manually. But neither is a great solution.

I don’t want to turn Proactive off, because it is sometimes useful. But it’s not dependable enough to rely on it, so I can’t simply decide to stop adding events myself. And even if it were, for things like flights, Proactive will only add the actual flight time. I need more than that in the calendar, for example:

  • The time I need to leave for the airport
  • Any meeting(s) I have at the airport before my flight
  • Any tasks I need to take care of from the lounge

So I don’t want to switch it off, and don’t want to rely on it – I instead want it to intelligently recognize when an appointment already exists, and to refrain from adding it.

Shared calendars

One could argue that it’s difficult for the app to intelligently de-dupe proactive events when manual and automatic entries may have different titles. But there is one example where it’s ridiculously simple to de-dupe, and absurd that it doesn’t do so: shared calendars.

My partner and I share calendars with each other so that we can make social arrangements when the other isn’t around. If I want to arrange something for both of us, I can see if Steph is free that evening, and if I want to arrange something on my own, I might want to schedule it when she is busy herself so we don’t end up never seeing each other.

The way we manage social events is one of us creates it in the Calendar app, then sends an invitation to the other one. But since our calendars are shared, each joint event ends up duplicated.

You can see in the example above that both a concert and play are duplicated – once as an event I created, and again as an accepted event in a shared calendar. That’s two dupes in one week, and that’s far from unusual. There is no excuse at all for Calendar failing to realise these are the exact same events.

Is this a problem you’ve experienced yourself? Do you have other examples? Please share your experiences in the comments.