Bryan O'Malley
“…and if I claim to be a wise man, it surely means that I don't know.”

WWDC 2019 Wish List

Here we are again. A week away from the 2019 Apple World Wide Developers Conference. Christmas Eve for tech nerds.

Each year I make a list of the things I’m hoping Apple will announce at the conference. Each one is a tangible upgrade that I think would be a huge improvement for the majority of the people who use Apple’s products. My track record has not been stellar in recent years, but who knows? Maybe this is the year that Tim Cook says, “You know what? That O’Malley kid has a lot of great ideas. We should do all of these ideas!

I don’t expect to see any new hardware at WWDC, with the possible exception of a sneak-peak at the new Mac Pro, so I’m restricting this list to just software updates.

Here’s we go!


Well, this is easy. Nothing on my list from last year shipped in iOS 12, so I’m just going to recycle them again this year.

  • Better Siri – smarter answers, read to me instead of listed on screen; the ability to unlock using my voice, the re-lock just as easily (recycled)
  • Better File Management – make it easier to get files on and off my device, then select the right app to use (recycled). The 2019 plus-up? Let me connect an external drive through USB-C.
  • Schedule Email Messages – write it now, send it whenever I want (recycled)
  • Schedule Text Messages – if the Email app can do it, why not iMessage? (recycled)


After years of neglect, Apple seems to be giving the Mac a lot of attention once again.

  • Better Copy & Paste – It took me a long time to jump on the clipboard manager train, but now I can't live without it. Paste finally changed my mind because the UI is exactly what I expect – a visual representation of what's in my copy history, at the bottom of the screen, with an easy search and the ability to paste while removing formatting. Honestly, I just want Apple to buy the company that makes Paste and then package it right into macOS. It's that good.

Then build it into iOS too.

Then synchronize them in real-time. I know that macOS and iOS are supposed to be able to synchronize the most recent copied item, but it works so infrequently for me that I don't even bother.

  • Better Window Sizing & Memory – Here's a common occurrence for me: I plug my MacBook Pro into an external monitor and work for a few hours – all the while opening apps and placing them exactly where I want them. Then I unplug and run to a meeting. When I return and plug back in, the windows are scattered all over the place with no rhyme or reason to which screen they'll end up on. Why?!? No 3rd party app I've tried solves this problem completely, but Moom is the closest.


I use tvOS every single day. Since I cut the cord it's my primary entertainment environment, and honestly, I think it's pretty nice. Sure, there are a few quirks, but it feels natural for someone who uses iOS on their phone all day. That said, I would like to see a few refinements…

  • Mute – I love the fact that I can easily change the volume using the remote, but I really, really, really want an easy way to mute the TV too.
  • Netflix – this may be a stretch given their competing interests, but I'd really love to see Netflix included in the TV app. Having one place to find recommendations for what I should watch would be nice.
  • Better Recommendations – speaking of the TV app, I wish it would get better at learning what I like and making better recommendations.


I'll be honest, I don't really care about the Apple Watch. I had the first edition and found it too thick, too slow, and without a killer app. It's gotten incrementally better since then, and my wife does like hers, but it still doesn't really excite me. That said, I can imagine one thing that might help:

  • Be a Watch – Don't make me shake my hand like I'm trying to rev a Harley just to see the time. If you're a watch, be a watch. Keep the time visible at all times. I have faith that the world's largest technology company can figure out a way to make the battery situation workable.

So there's my list. What's yours? Hit me up on Twitter and let me know.

1 – Okay, neglect might be too strong of a word, but they certainly made the Mac a distant second (third?) behind the iPhone.

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