Ever since Steam updated their checkout UX (probably well over a year ago by now), I fall into this trap almost every time I gift someone a game. In the screenshot the design seems pretty clear: Continue with the checkout process via the big blue button on the right. Leave the checkout process and add more to the cart via the “secondary” button at the bottom.

However, the whole flow of buying a gift goes from top to bottom – before you even see the screen as shown above, you have to pick a recipient. Doing so expands the form downwards, unveiling the various options for the gift. First you enter the message, then you go down one to (optionally) add a custom signature, then you go down one for the delivery option, then you’re all set and go down once more to proceed.

Except that you don’t proceed with the button that you’re naturally drawn to. Instead you leave the process and find yourself back on the homepage of the store. Luckily they started saving the gift details you’ve entered a while ago, but initially I had to re-enter things a couple of times.

Speaking of Messages… as hard as I found that to believe myself, somehow things there got unimaginably worse about a year ago. I don’t know when or why exactly it started, but Messages has been permanently out of sync on my Mac so badly that it is barely usable anymore.

The conversation above is from July 2024.¹ Looking at the timestamps: Philipp answered 30 minutes after the hilarious meme I sent. His response arrived on my phone immediately. 18 minutes later I returned to my Mac to check out the links he sent, but no sign of the messages there. From experience I already knew that sending another message myself would get things unstuck – that’s what is shown in the video. Once it catches up, things work without any delay – until it gets stuck again as I use Messages on the phone or my work Mac.

This affects all my conversations (I only still use Messages with three holdouts that haven’t moved on from Apple), and has gotten worse over time. In the beginning it would catch up on its own after a few hours. Now it is often several days behind. Responding myself to “force a sync” as shown in the video doesn’t work instantly anymore. Sometimes it only seems to partially catch up – e.g. loading the last two of five missing messages in total. I lost any trust in Messages on the Mac showing me the full content of conversations, erasing what little remaining value that service still had to me.

Maybe I could fix it by reinstalling – logging out of iCloud and logging back in didn’t help. But frankly, I don’t care anymore. I moved on from macOS for most parts of my personal computing, and I expect to fully rid myself of it this year. Besides life being busy, that’s a main reason for the decrease in postings here. Our criticism, petty as it often may seem, usually means that we genuinely care. When you care about something, that comes with a desire for improvement and an expectation of higher standards. I stopped caring about Apple long ago – seems as good a time as any to articulate that.

I wasn’t even aware that Messages allows selecting multiple conversations until I accidentally ended up in “multi-selection” mode… with just a single conversation selected. Slightly less useful than showing the actual content of said conversation. No idea how it ended up like that, and I have not been able to get into that state intentionally since.

I wish Slack would spend half as much time on improving core functionality as they do on these obnoxious, enterprise-grade notifications for features I don’t need.

This one is particularly dumb: It’s from a Slack workspace with exactly two users – me included. All our communication there happens in channels.

Security prompt annoyances are kind of a low hanging fruit these days, but I will never understand how Apple decided that this experience after an upgrade is acceptable.

Recently I was invited to a Uber for Business account and was rather surprised by how bad that onboarding flow was.

First off, my iPhone was not able to scan the QR code from this email. I don’t think I have ever seen a QR code with that complexity in the wild, but generally I’d describe iOS’ ability to read QR codes as “dark magic”. I have never encountered one that it couldn’t read, and it is lightning fast – always recognizing them before the image even auto-focuses. That’s why I was so surprised when this code didn’t work. I assumed it must be broken entirely, but tried again. Even after zooming in the browser and trying many times, no luck. (Oddly I wasn’t able to reproduce this later, scanning now works fine – not sure which exact part of technology was annoying here earlier.)

So I went through the process without the QR code. I changed the PIN code for the screenshot, but the actual code also contained a number zero 0. Not a capital O character, as I found out after entering the wrong one first. The font choice does not make it very obvious.

But before even being able to enter this PIN, I had to find where. Luckily they provide instructions in the email – unfortunately, they are not correct. I was on the latest version of the “same Uber app you know and love”, but no Add another business profile option. Once I found what was meant, the option to enter a PIN code also used different wording.

Entering the PIN was an adventure as well – apparently they have 8 digit and 9 digit PINs, so the dashes they force-display between the different segments of the PIN look incorrect up until you entered the final digit.

I know it sounds very nitpicking, but this stuff is why scams work. Normal people do not have the capacity or ability to distinguish lack of care from fraud. I see it when talking to relatives and friends all the time, and I even notice how much more energy I have to waste myself to stay vigilant.

Amazingly, that was the second fail after I upgraded my work machine to Sequioa. Initially I was greeted by this screen – I didn’t bother making a video, because you couldn’t have seen anything. Literally nothing was clickable: Not the More… links, not the checkbox, not the Cancel button. Nothing in the background window either, of course. I clicked and double-clicked on everything like a madman. I tried Enter, Space, Esc… nothing. I had to force-quit System Settings, and then I ran into the issue in the video above.

I was only able to proceed with both actions after a reboot.

Nothing more reassuring than a cute little UI bug right on the login screen. Prioritizing security above all else!

Deleting something from a list while it is showing filtered results? I’m afraid you’re gonna need at least an M5 chip for that kind of pro workload.

At launch I was genuinely excited about Shortcuts, having already used them back when it was still the Workflow app. Five years into Shortcuts being a first-party solution, they are so painfully unreliable that I’ve given up on them except for the most basic and non-critical things.

I invested a fair bit of time and energy into setting up some cool shortcuts initially, and it is cool what you can achieve with them – in theory. The effort required even for simple things is painful to accept as someone who’d be able to use an actual scripting language. Some of that can be overcome by pairing it up with Pythonista, Rubyist, Scriptable and similar things. Still you remain limited by Apple’s shortcomings¹ when it comes to versioning and syncing.

But I’d probably accept all that if the shortcuts themselves would reliably work. Sadly, almost all my shortcuts have stopped working over time. Mind you, not because of planned deprecations/changes in the actions I used with clearly communicated workarounds or alternatives. No, just random errors like in this screenshot. No explanation, no recourse. And it’s not due to updates – things just stop working from one day to the other.
Searching for something like that online at best will unearth an Apple Support Community thread from someone else having the same problem, where an incompetent volunteer sporting a “Triple Elite Question Hero” badge responded to suggest resetting your phone, Mac and router – and maybe also getting a different ISP or moving countries. If you think reaching out to actual Apple Support about a problem like this is a worthwhile endeavor, I would like to connect with you to discuss a bridge with very competitive pricing.

My favorite shortcut was a “Clip it” feature for my own Plex server: It ran a Python script in Pythonista which connected to my Plex server’s API to retrieve the filename and timestamp of what I was currently watching. It then passed that data to a custom script on my server which executed ffmpeg to cut a 60s clip out of that file and returned it via HTTP. Shortcuts passed that clip into the trimming action and then the share sheet. A perfect way to share a good joke or other reference with friends quickly. It worked great, and it gave me joy every time I used it.
Until it stopped working – the trim action suddenly wouldn’t accept the videos anymore. Some cryptic error. Neither the iOS version, nor anything on my Plex/web server had changed. Since iOS is a toy, you have no good way of debugging yourself. Here I actually was able to debug a bit because things are partly happening on my server. I verified that (to the bit) identical video files that worked in the past are now inexplicably not accepted by the video trimming action anymore.

How could I ever again justify spending all the extra time to work around/against the already restricting and complicated nature of Shortcuts to get something like this set up, when it will just randomly stop working at some point?

To clarify – the error from this screenshot is a different one. From a far less complicated shortcut. In fact, I believe the “Make GIF” shortcut is a built-in one. It just worksn’t.™