Apple has tried to fix the iPad four times. First in 2015 with the introducing of Split View, picture-in-picture, and better accessory support for keyboards and the Pencil. Then they immediately took a year off. iOS 10 on the iPad sort of phoned it in. It became abundantly clear that they either could not or would not update the iPad as aggressively as it needed. The following year, iOS 11 brought the second wave of major changes with the advanced dock, drag and drop, the Files app, and more adjustable slide over. This was a big year and it showed that there was a clear willingness inside of Cupertino to push the iPad harder. But then again, another year off with iOS 12. Then the third major fix year arrived with the introduction of “iPadOS” as a dedicated platform for the first time. It brought multi-window support to apps, way better slide over support, new gestures, and plenty of other goodies like Home Screen widgets. As you might guess, iPadOS 14 felt like another year off despite a handful of smaller tweaks. iPadOS 15 did not go big though, despite what Apple wanted us to think. It brought new multitasking controls to make everything a bit more obvious to users, but it did not fundamentally change the way things worked. Then iPadOS 16 arrived and sort of blew everything up. Stage manager alone was a massive addition, providing adjustable window sizing and external display support. A common theme however among these updates is that while they were great at the time they launched, they were simply never enough. After stage manager and the reaction users had to it, iPadOS stagnated for two years.

Today, Mark Gurman reports that they are going to try once again with iPadOS 19 to make the iPad a more advanced computing platform. Color me skeptical. Is this a fifth time’s the charm situation? I am trying to be optimistic, particularly after Apple nailed multitasking on visionOS. Plus, this could imply that they have been working on these improvements for three years given the lack of massive updates since iPadOS 16. Mark says that the update will “focus on productivity, multitasking and app window management — with an eye on the device operating more like a Mac.” That sounds promising, but it is unclear what that actually means. Combined with a visual redesign, this could be huge if they do not tiptoe again. Each time the company has attempted an iPad software update to make the device more Mac-like they try too hard to do something different and often end up making something inferior as a result. That cannot happen this time. I seriously hope that they know it.