My Crazy Wishlist for Apple’s iPadOS 14

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It’s June and WWDC is just a day away. A little later than usual this year and online-only thanks to the pandemic that we are all living through, but still here. The show will go on starting Monday at 9 AM Pacific.

It’s sure to be a lot different than what we are used to. but I’m betting that Apple will still deliver a polished and very professional presentation. They have quite a rep to uphold as the best in the business at this sort of thing. I doubt they will drop the ball, even under the more difficult circumstances.

We are a year out from Apple’s introduction of iPadOS during the last WWDC Keynote. The separation of the iPad from the iPhone and iOS came with several features that many of us had been waiting a long time for. It was as if Apple execs and engineers had been keeping a checklist of pro feature requests and made it a point to check as many as they could in one update.

2019 and the introduction of iPadOS set a very high bar, but no yearly update can cover it all. Apple still has plenty of work to do to make iPadOS a more complete computing experience. They still have features to add and polishing to do and Monday we will find out if they have decided to keep up the currently brisk pace of updates or drop back a bit and focus on polishing and perfecting.

I had a good run with predictions early this year, but I’m not going that route for this Keynote. I’m going to stick to a wishlist for iPadOS and hope that Apple gets around to most of it on Monday. Frankly, a lot of the stuff I expect or want to see has already been covered by other iPad fans and Apple and other tech outlets, so I will stick to what I hope we get and leave it at that.

Extended multi-display support

I was torn on whether better support for multiple displays would come this year or next. I felt more certain about full mouse and trackpad support in iPadOS 14. However, since Apple delivered the latter in a surprising iPadOS 13.4 update a few months ago, the former feels kind of expected at this point. I guess that’s because better support for extending display possibilities is one of the most common desktop computing features that hasn’t made its way over yet.

I think there is a lot of current demand for extended multi-display support among iPad fans and pro users, as well. The ability to go beyond the iPad’s own screen with multiple apps would really take the OS another step forward. I think that the popularity of the Shiftscreen app for iPadOS,  which adds some extended capabilities to a second display for web pages and apps, proves that some of us have a use for such a feature and are interested in doing more with our iPads.

Another key to getting extended multi-display support has been the removal of barriers to use. Support for multiple displays was possible with a Lightning port, but it was never ideal. Apple’s move to USB-C on the iPad Pro in 2018 was important because it opened a door of possibilities for simultaneous charging, as well as using other peripherals besides another display. This was the first big hurdle.

When the iPad’s only input method was touch, extended display support was impossible to take advantage of. How can you control extended content on another screen that isn’t capable of sensing touch? Now that we have mouse and trackpad support, that barrier has been removed, as well. Now there is nothing stopping Apple from giving power users the capability to greatly expand what we can currently do with a connected monitor. I really hope this made the cut in iPadOS 14.

Multitasking improvements

I appreciate that Apple added multitaking and dual screen apps to the original iPad Pro and they have gradually upgraded the concept over the last 5 years. However, while this feature is quite capable, the implementation is a little less than intuitive. Getting apps into and out of Split View and Slide Over modes is touchy in a literal sense. It’s also not as easy as it should be to get apps that aren’t in the Dock where you want them in multitasking.

I don’t claim to have the answers here. There have been a few propositions from the community that looked pretty good, but ultimately it’s up to Apple to give us power features that make a little more sense. The more accessible the feature is, the more people will take advantage of it.

Configurable keyboard shortcuts

Speaking of the Magic Keyboard, Apple could stand to add a little additional functionality to their keyboards. Most Bluetooth keyboards set up for use with iOS and iPadOS devices come with dedicated function keys but Apple avoids doing this. There are obvious reasons with the new Magic Keyboard due to its design, but even the original stand-alone Magic Keyboard doesn’t have them.

A perfect way to get around this lack of dedicated shortcut keys is to allow users to set up their own shortcut combos. This would be perfect for things such as adjusting the keyboard backlight on the Magic Keyboard. Currently, the only way to do this is to dig into Settings or use a Shortcut to get you there. Some code for something like this showed up in a recent iPadOS beta, so maybe we will get it this year.

Multi-user support

This is another one of those desktop computing features that iPadOS still lacks. Apple’s tablet OS could definitely benefit from the ability to set multiple user accounts, as well. Many families share an iPad between them and having the option to set up separate accounts, especially for kids, would be a valuable addition.

Apple already offers this capability for iPads used in schools, but it currently requires a server on the backend to work. However, this does mean that there is an existing framework that Apple can port to work stand-alone on the device.

App Switcher improvements

Apple did a good job improving the iPad’s App Switcher last year to make it more functional. It went from showing only the last split view combination that an app was in to displaying multiple setups for any given app. This was a big step forward, but a little more remains to be added.

First off, it would be nice if we could save entire multitasking app setups, including apps in Slide Over. For those of us who use particular groups of apps in certain positions for writing or researching, this would be PERFECT. One tap in the Switcher and you are ready to get right to work.

Along the same lines, having the ability to pin favorite multitasking app setups in the App Switcher would take things to another level. Again, it’s all about convenience and efficiency. For those of us who are more on the power user side of things, this would be another solid time saver.

Home Screen improvements

The large screen of the iPad begs to be put to better use. Apple did give us the ability to move widgets onto the main Home Screen in iPadOS 13, but there is so much more that could be accomplished there. 10.2″ to 12.9″ of screen real estate is a lot to work with.

I can almost understand the static nature of the iPhone’s screen, but the iPad is different. Why not allow us to place widgets wherever we like on the main Home Screen. Yes, yes, I know. Android has had this capability forever, so don’t at me. However, I think it would work well on the iPad today. The ribbon is still useful, but there are a few widgets I would love to keep on the screen all the time.

I would also love to have the capability to put apps and folders in groups on the screen with whitespace between. Even better, why shouldn’t we be able to pin folders or files from the Files app right onto the Home Screen? Going a step further, how about the ability to tap and hold on a file to determine what app to open it in? While we’re at it, why not let us pin Shortcuts right to the Home Screen. That’s a power user’s dream right there. All of these things just add an extra bit of flexibility that make iPadOS that much more suited to the work power users want to do.

One last bit I would love to see come to both the iPad and iPhone is a little bit of watchOS. It would be interesting to see widgets expanded to include something more modular like Complications. That would be a great way to present small bits of information on the Home Screen. I think it would work well on larger screen devices, too.

The app List View is another such watchOS feature that I want to see on the iPad and iPhone. While it is probably more suited to the iPhone’s screen, I would still like the ability to present more apps in a single space. The ability to designate a secondary Home Screen as a List View screen to show all apps would be a great way to allow users to keep the total number of screens to display all of their apps and folders to a minimum.

Spotlight Search updates

Right now, Spotlight Search on the iPad just displays a single column of information when a search term is typed in. As with the Home Screen, this just seems like a waste of the screen real estate. Why not a two column layout with more information displayed at one time?

There’s one more thing I’ve been wanting from Spotlight for a while. Siri searches currently aren’t an option in environments where voice searches aren’t appropriate. What is preventing Apple from opening Siri up a bit and allowing search requests to be entered via text in Spotlight? With the focus on using physical keyboards with iPads growing, thanks in large part to Apple’s Magic Keyboard, this makes a lot of sense. It would also port over to macOS quite nicely.


There are more things I could list here that I want to see in iPadOS 14. Notification Center improvements would be welcome. People have been wanting the ability to set alternate apps as defaults in iOS since the App Store opened. Shotcuts could use even more power and flexibility. Allowing third-party clipboard managers to directly integrate into iPadOS the way that password managers can would be another great power user feature. However, I am going to call it here.

I don’t think we will get all of the above this year in iPadOS 14. However, I do think we will see at least half of the items on my list at least touched on during the Keynote. Who knows? Maybe Apple will surprise us and give us most of this and more. All I know is that they blew me away last year with the introduction of iPadOS and I hope they can do it again on Monday.

What do you think of these features? What do you want to see added to iPadOS 14? Let me know in the comments below or on Twitter @iPadInsightBlog.



James Rogers

I am a Christian husband and father of 3 living in the Southeastern US. I have worked as a programmer and project manager in the Commercial and Industrial Automation industry for over 19 years, so I am hands on with technology almost every day. However, my passion in technology is for mobile devices, specifically Apple's iOS and iPadOS hardware and software. My favorite is still the iPad.

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