Apple Papercuts - Tao of Mac

Rui Carmo

Tao of Mac

May 18th 2026 &middot; 10 min read<br>&middot;<br>#apple<br>#automation<br>#calendar<br>#homekit<br>#icloud<br>#ios<br>#ipad<br>#mac<br>#macos<br>#mail<br>#rant<br>#siri<br>#swift<br>#xcode

Apple Papercuts

I know this blog has strayed a fair distance from its Mac-centric origins, but I’ve been keeping a mental list of all the things that are broken, missing or inexplicably neglected in Apple’s software, and it’s gotten long enough that writing it down feels like a public service1.

This isn’t about Liquid Glass or grand design failures–those are well documented elsewhere. This is about the small stuff. The papercuts that, individually, you learn to live with, and collectively make you wonder whether anyone at Apple actually uses their software.

Despite the somewhat surprising length of this post after stitching together all the notes, I’m actually focusing on the things I hit every week (not trying to put together an exhaustive catalogue), and others will have their own lists–and that’s part of the problem.

Mail<br>Apple Mail is the first app open every day and the one I find hardest to defend, and I’ve been defending it for twenty years (longer if you remember the original NeXT mail client).

The broader story is one of abandonment. Mail.app used to be extensible–there was a plugin API that third parties used to build genuinely useful tools (GPGMail, SpamSieve, Act-On, all manner of filing and productivity helpers), and I used it to, among other things, have HJKL keybindings.

Apple deprecated that API, replaced it with a (much more restrictive) MailKit surface in 2021, and proceeded to lock MailKit down so hard that barely anyone shipped an extension.

And then they quietly stopped mentioning it. The result is that Mail is now less extensible than it was in 2010.

In particular, in this age of desktop AI agents, I come time and again across the fact that AppleScript support in Mail has been left to rot. I wrote about getting raw message source via AppleScript years ago, and even then it was a workaround for missing functionality.

Today the dictionary is unchanged, the bugs are unchanged, and the "Apply Rules" menu option–which used to let you re-run rules on selected messages–no longer works consistently on multiple selections, if it works at all.

And searching for messages is such a travesti of a user experience that I’m not even sure how to describe it–suffice it to say that it never searches solely inside the folder I’m in and that it often fails to find messages that I know are there, even with the most basic criteria.

Mail on iOS Is Just Consistently Worse<br>And then there are the basics that have simply never arrived on iOS:

There is no way to filter messages on an iPad. Not "limited filtering"–none. You cannot create a rule, you cannot sort by sender, you cannot batch-select by criteria.

Smart folders don’t exist on any iOS version (no, the stupid Categories thing doesn’t count). They’ve been on the Mac since… 2004?

And, of course, there is no way to have Mail rules sync from the Mac to iOS. For a company that talks endlessly about ecosystem coherence, this is bizarre.

Download progress is opaque. When Mail is pulling thousands of messages from an IMAP server, the feedback is either nothing or a tiny spinner.

Apple Intelligence in Mail amounts to a summary button that occasionally produces useful one-liners.

There’s no smart filing, no suggested rules, no priority inbox–nothing that would actually reduce the cognitive load of managing email. Gmail had most of this a decade ago.

Time Machine<br>I wrote an entire blogpost about how bad it is these days, and if I had the patience, I could probably write twice as much.

But I’ll just add that the performance is abysmal if you have thousands (or millions) of small files, and that things like asimov (or manually setting the right extended attributes manually for excluding development folders, something I routinely forget to do) shouldn’t exist, because it should work properly in the first place:

It should have much more transparent progress indications

It should never fail silently

It should recover gracefully from failures

It really should suggest automatic exclusions and have a proper UI that is not "Add this huge top-level folder" for exclusions

Again, this isn’t rocket science. I installed Borg Backup the other day on some of my Linux VMs, and it is so good that it defies explanation how Apple still hasn’t gotten this right.

Search<br>Craig Hockenberry recently wrote up an experience that captures the problem perfectly: his iPhone’s Spotlight index corrupted, search stopped working across App Library, Mail, Notes, Messages and Settings, and after trying every remedy he could find online–forced restarts, language changes, toggling Siri, developer mode reindexing–the only "fix" was a full device backup and restore.

Which took hours, broke Apple Pay, reset FaceID for two dozen apps, wiped TestFlight builds, and generally made his...