If only there was some indication that this shortcut is not something I’d ever want to run at 3pm in the afternoon.

I dunno, something like it being named “Going to bed”. Or the fact that for about 90 days in a row I have exclusively and always triggered this shortcut between 11pm and 2am.
But maybe I’m just too subtle – I already dismissed this type of suggestion twice after they randomly popped up during the day… how could Siri ever learn what makes sense with such a lack of clear indicators!

Good thing the new and improved Siri with “AI” will fix all of this silliness. Any day decade now!

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.