Every June, during WWDC, Apple announces their big OS updates, and every fall, those OSes ship. There’s always something pitched to app developers to adopt or adapt to, it’s all kept as secretive as Apple can manage until it’s revealed to us, and we then have the opportunity to chase some or all of it for day-one releases with the OS in roughly three months.

Especially for an indie, choosing to chase features from WWDC can be a big deal, pushing aside our own product goals or customer requests for Apple-driven work. We’ll need to download the betas and ride out any early bugs, figure out how to maintain (or whether to drop) older OS support in our codebases, and work with in-flux SDKs. In exchange, we hope to improve our apps, keep current with the evolving look and feel of the OSes, and be part of the flurry of press, App Store features, and social media buzz when the OSes do land.

I’ve chased “dubdub”, to some extent, three times (that I can think of now) during TimeStory’s six years of development, including this year we’re at the end of, and have some reflections.

The Big Sur UI refresh (WWDC 2020)

Big Sur changed the basic window design in a way that made non-updated apps immediately stand out, and I liked the overall look of the new unified toolbar. (I do still miss the old standard of rich, irregular macOS app icons that Big Sur moved us away from, but in my case, my old icon was pretty rough, so it was easy for me to move forward to the new style.)

The work was relatively straightforward and easy to conditionalize by OS, and I shipped it in time for day one. I was happy with the result and it left me in good shape for future updates.

Shortcuts in Monterey (WWDC 2021)

MacOS Monterey added the Shortcuts app and corresponding Intents framework from iOS to the Mac. I was excited to add easy end-user automation to my app. I particularly hoped to be able to respond to feature requests with “you can do that today, with this shortcut”. I quickly prototyped it with help from a great WWDC lab session, posted a public beta, emailed a few people in the press who covered app automation, submitted to Apple for an App Store feature well ahead of time, and shipped in time for day one. (Original dev blog post.)

Results?

• No press or App Store coverage. Not too surprising; many less-niche apps built great Shortcuts support at the same time.
• The feature is genuinely useful. I’ve used it myself, built several useful examples, and have in fact offered shortcut-based solutions to customer emails. But it’s much less of a selling point than some customer-requested timelining features that I might have done instead.
• No measurable bump in sales compared to any other app update.

And, frustratingly, the very next year, Apple announced App Intents, a completely new framework for exposing Shortcuts actions. It’s much more pleasant to work with as a developer, and has since then been extended to integrate better with other OS features like Spotlight. And it immediately rendered my implementation legacy code. Rather than maintain parallel old and new implementations, I just let the old code sit. (In 2025 I finally dropped Monterey support, and can start migrating over.)

I often wish I’d waited on this feature. I like it, but I don’t think the ROI was there, and it was really only appealing to a limited set of my users.

xOS 26 UI Updates (WWDC 2025)

Fast forward to this year. WWDC25 included a ton of new UI stuff, including the much-discussed Liquid Glass; some of it I liked, some of it less so. What pushed me over the edge in deciding to chase at least some of it was installing the first beta of macOS Tahoe. It was clear that non-updated apps would immediately stand out, from the radius of the window corners to the look of standard controls, and I wanted to make sure my apps looked well-maintained. I decided on a major (dot-zero) release number to give me a bit more license to update the UI than normal, and dug in.

My personal favorite WWDC25 announcements, by far, were the adoption of Mac-ish menu bars and overlapping windows on iPadOS 26. I use productivity apps on my iPad Pro, in addition to writing one, and these have been long-needed. They were both relatively easy to adopt, as well, both being built on existing SDKs from iOS 18 and before, only needing more polishing, testing, and in the case of the menu bar, auditing and filling in missing items. On its own this was an unreserved win.

I also liked the idea, for canvas-style apps, of moving a few carefully-chosen controls out into floating glass layers over the document canvas. Apple’s benchmark here is Freeform. On Mac, I already had a similar pattern for a scroll control (using traditional blur visual effects rather than the new glass effect), and I now applied it to time scale and document zoom, two things that to me make the most sense floating at the bottom of the window.

This, unfortunately, turned into a surprising time sink. There was a lot of churn, with each macOS beta changing at least something about how glass effects looked or behaved. Different control types applied glass effects inconsistently (and still do, in the released versions). When presented over a white background, glass layers become hard to spot without additional tweaking. This resulted in many hours of experimenting and iterating, far more than the size of these controls would imply. I’m pleased with the final result, but expect to keep revising it over time.

One thing Apple pushed for, which I did not adopt, was to extend blurred document content up under the toolbar. I tried, over many hours, repeating with each new beta, but it never worked out. Timelines are often colorful, text-heavy documents, and frankly the app looked awful when the wrong strip of the timeline would scroll under the toolbar. (App developers have very little control over this; we just extend the content up, and Apple’s code applies the blur and glass effects.)

There’s more to this story, but this blog post wasn’t meant to be a technical deep dive. (I also want to note that we took on other work, including some substantial new user guide authoring, at the same time; the 4.0 release cycle wasn’t just chasing WWDC, unlike the prior two examples.)

The main result here is that the release took me so long to develop that we ran into some previously-planned travel. We were able to work during that incredible trip, but not every day (Hemi wrote about it on her blog), and the final release wasn’t out until December. I’m happy with many of the UI updates we made, and happy to have gotten past this to unlock future development, so I can’t really say I wish I’d waited. But still, the cost-benefit ratio was pretty high, and the non-Apple-driven feature content I shipped in the second half of 2025 was a fraction of what I’d planned at its start.