How and why tagging needs to be improved on macOS and iOS

The wishlists for iOS 13 seem to be appearing especially early this time around, partly because the hardware (like the new iPad Pro) is at the point where it’s so clearly the software that is holding things back.

So I’d like to make the case for “major improvements to tagging” as something at the top of my wishlist for the next iteration of Apple software (and any of this can come in a “point-update” like 12.2 or 12.3, that would be more than fine with me!)

Despite Apple’s hesitant, haphazard implementation, tagging is gaining traction with users and developers. Tagging provides a powerful way of pulling together the stuff you need for a particular meeting, or project, or trip without having to duplicate the files or move them out of their home locations. In addition, tags provide a handy way to cross the macOS-iOS boundary: by tagging a couple of files you’re working on, you can use the tags to find them quickly on the other platform. That’s the idea, but Apple is far from implementing this in a consistent way.

My hope for iOS 13 / MacOS 15 is that Apple will finally take tagging to the next level. People who only have 8 tags may be perfectly satisfied with what Apple now offers. But people with only 8 tags probably don’t really need tags in the first place. Where tagging is really helpful is when you’re responsible for lots of different projects, clients, courses, etc. And then, you quickly have dozens if not hundreds of tags. And for this, what is available on iOS is completely inadequate. Searching is great for finding and opening that one item. Tags provide a way of gathering stuff together for what you’re working on, and going back to it.

Here’s my wishlist:

What iOS needs to inherit from macOS

  • The organization of tags in Files needs a major overhaul: in the “Recents” tab, files are grouped by tags, but the order of those tags seems completely arbitrary. It’s certainly not by “most recent,” it doesn’t parallel the sidebar order, and there’s no way to alter it. Bizarre.
  • The field that opens for “Add New Tag” should autocomplete with existing tags (and if there’s no match, a new tag is created), like on macOS.
  • In iOS, it should be possible to add a tag when using “Save to Files” (e.g. to save an attachment from a Mail message). A long-press on “Add” could permit an “add-plus” function, whereby you could first add a tag before saving to the selected folder.
  • When displaying files by a selected tag in the Files app, the names of other tags should be visible – not just as colored dots. Perhaps the “Size” column be switch to a “Tags” column when tags are selected?
  • It needs to be possible to turn off autocapitalization for new tags in the helper tray.
  • Tags on iOS should parallel macOS in parsing the component parts of punctuated tags e.g. home:receipts and work:receipts would both found with a search for “receipts.”
  • It would be nice to set (a few) custom keyboard shortcuts for frequently-used tags.
  • In the Finder on macOS, if I select a tag in the sidebar and then enter a search term in the Search window, a get a selection of the files that have both characteristics. In iOS, it generates a search that completely ignores the fact that I just selected a tag from the sidebar.

More General Tagging Problems

  • The organization of tags in the sidebar of both Finder and Files needs to be more sensible and sync quickly cross-platform . No one wants to have to pick through dozens if not hundreds of tags in the sidebar. It would be great to toggle a few on/off as favorites (that sync quickly), but tags in the sidebar should be sortable by name, date, and size (number of tags) and (ideally) nested into a few groups.
  • There needs to be a way of searching for multiple tags (with “and” as well as“or” searches): Selecting multiple tags (with ⌘-click or ⇧-click) or typing/autocompleting should narrow down the items displayed to an intersection of all. For example, selecting the tags “WWDC2018” and “travel” should reveal only items with both tags. And using the “or” option would reveal files with either tag.
  • Something needs to be done about the confusion between keywords and tags. Partly because Apple was so late the tags party, when it finally started introducing native tagging with OS Mavericks, we ended up it “Mavericks tags” (since renamed “Finder tags”) as a parallel system to metadata that apps referred to as tags, but which appear in the metadata as “keywords” (or, less commonly now, OpenMeta tags). As a result, there is a confusing array of proprietary uses of keywords (sometimes referred to as tags), requiring separate databases to be maintained for app-specific keyword systems, as well as inconsistencies between how tags/keywords work (e.g. DEVONthink ignores the “@“ symbol in tags). For example, the indispensable program MailTags actually assigns keywords rather than tags to email messages (unless there is also an identical Finder tag).
  • As a related point, it would be great to make it possible to assign tags to any file. Why can’t I tag items in Notes, or Photos, or Mail? In Photos, for example, you can assign keywords to photos, but it’s a pretty cumbersome process, and then you still can’t search for them with Spotlight. Real, unified system of tags is what is needed. A unified and reliable native system of tagging would allow developers to make much greater use of tags to build smart folders which could then sync across iOS / macOS.
  • Then there’s the bizarre bug in macOS that I documented elsewhere, which disables keyboard shortcuts for adding tags in the Finder, unless you have emptied out the “Favorites” box in the Finder > Preferences.

Reaching for the stars

  • What I’d really love to see is a tag cloud view, along the lines of Cover View, which (in Finder or Files) would would display the files’ tags as a “word cloud," with the number of occurrences of that tag in that file selection determining the size of the tag’s depiction. (The feature of being able to assign tags a color would make this particularly interesting.)
  • As a final bit of crazy talk: why not rename the Finder on macOS to “Files”?
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I’ve given up on using tags for organisation, as half-backed, as they are. I only use them as “done”-check for Hazel scripts. But the half-backed implementation of Tags is in line with other things introduced in last years. Look at spaces, for example. A great idea, but they lack the most simple things, like a shortcut to move a window to a space left or right of the current one. You also can’t attach a window to a particular space. Some of these things can be done with hacks in KM or BTT, but in general it remains a not often used tool due to bad implementation.

I agree, I use tags all the time and they save me a lot of time. It’s the first place I got for commonly used files. Not having them on iOS means I have to finish everything I do on the Mac.

For me, file management is still the thing holding iOS back, it takes much longer to do anything compared to macOS. Also, text management (selecting, copying etc) is much slower too.

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@JoelAnderson This is a great post!!! I don’t really use tags, but this alone makes me think I should especially as I move to more file-system-based file storage vs Evernote and DT.

Thanks for sharing this and I agree with your wish list!

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Thanks! You raise a good point about Evernote and such. I actually think that, if Apple had done a better job early on of sorting out meta-data attributes (especially tags), the there would have been less of a need for Evernote, DevonThink and others to seal stuff up inside of packages, generating endless headaches for sync and export.

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There are good reasons for doing so, not related to the current mediocre tags implementation: better indexing, search, better import and encrypted sync over the provider of choice - which can be as well iClould. Just accept that file systems are tools which were never intended for an advanced AI-supported knowledge management. Thus, some people (like me) are pretty happy to rid of them completely at least for some tasks.

P.S.: Sync is seamless, and so is export. Actually, I could access all files even without export, it is just a package with files + index metadata + backups. Sorry, but this is FUD or a complete lack of knowledge.

I don’t mean to hate on DevonThink (or anyone). They’ve come up with brilliant solutions where Apple dropped the ball. My main point was that this all came about because Apple didn’t provide excellent indexing, search, and sync themselves, but I don’t see why they couldn’t. Also, to nuance the point about “headaches”: what’s been frustrating has been trying to see stuff inside packages alongside stuff outside packages as results in the same search in Finder. I’ve had less experience with DevonThink, but my experience with bibliographic databases like Sente (RIP) and Bookends, is that you can’t see many of the keywords without opening up the application.

Honestly, I don’t think it was ever their intention. Both are very specific applications for a very specific kind of problems. It is not something one would put in a file system. Even if all mentioned critic on current implementation of tags would be solved, we would still get only a “devonThink light” as an output. Tags solve only one problem - file systems are strictly hierarchical and file-based, but we mostly work with documents and don’t care so much about file system inodes. In a similar fashion, Spotlight does its work for a fast search and access. But some people need auto-classification, complex search queries and so on. As a launcher, it fails short of LaunchBar, but would you let your mother use LB? I would certainly not.

I think, what most people does not get right, when they talk about macOS, is why it is so great. Not because it is jack of all trades (it is somehow), not because it has so many utilities (it has), but because it has done its basics right - there is a lot of hooks and interfaces, so third-party software can use it. This is the reason for all the Hazel, KM, LB, Alfred, DT and so on around us.

So, do we need apple to build all this? No. But we need it to do the basics right. Sadly, the tendency in last years is just to throw half-backed solutions, which make automation between apps only more difficult(Hello, Mojave, and your stupid and non-transparent permissions). I have a feeling, that they don’t care that much about powerusers anymore. JXA was released some years ago and completely forgotten after the release - still full of bugs with no proper documentation, so I prefer to use AS, as ugly and strange as it is. Spaces lack some basic polish and so are tags. We have Marzipan on our radar now trying to get us on the level of iOS and I fear that should it work macOS automation will be dumbed down on the same level as iOS. Just because it is not a priority.

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I completely grant your points about what’s so amazing about macOS. I get 80% of my work done on a 5K iMac, and if that number were 100%, I wouldn’t have written the post. It’s just that I’d really like to go iPad-only when I’m away from home. Instead, I find myself bringing my 2012 MacBookPro with me (in addition to my iPad), because the file management on iOS is so half-baked that I regularly have to turn to the MBP to find mission-critical files.

The fear that implementing this across OS’s will require dumbing down aspects of macOS that power users rely on… I get that. But I’m not seeing how such dumbing down would be required by any of the points I mentioned under the heading “What iOS needs to inherit from macOS”. Basically, I’m just looking for (1) easy tagging interface on iOS and (2) and complex search queries on iOS. None of this requires a UI that overwhelms anyone grandparent, either. Apple just needs to finish baking what they have in the oven.

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I agree. That would be a nice feature improvement. I’m not much of a tagger, but when I need it, I need it to work universally. I think another hurdle, other than Apple, is getting developers to incorporate tag recognition, display, and editing into their interfaces in a consistent manner on both macOS and iOS platforms.

@ptarh Are you saying Dropbox sync is not encrypted?

Ubiquitous tagging across apps would be absolutely brilliant! I don’t see it happening anytime soon but it would make my life a lot easier.

I’d also like to see a good implementation of nested tags.

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You should be always aware that Dropbox can and will read your stored files. So I would never push important files unencrypted over cloud services - including iClould.

@ptarh Thanks. I will have to read their TOS closer because their security pages talk about everything being encrypted at every stage. That article was from 4 years ago - is it still current?

I appreciate the heads up.

I think it is current. You have to distinguish between encryption of your connection to Dropbox and encryption of data. Dropbox does the first one, but not the second one. Actually, it is even better - they do the second one, but they store all the keys and thus are able to decrypt your data every moment. The equivalent of burglar having the keys to your door. Here a small article on that: https://www.comparitech.com/blog/cloud-online-backup/make-dropbox-more-secure/

Ummm that article says DB checks the hashes of files you share against a list of known hashes for copyrighted files. First, hashing can be done without reading file content ( https://security.stackexchange.com/questions/168492/how-does-file-hashing-works ) . Second, the article says nothing about files you’re not sharing.

There are probably reasons to be concerned re DB but you should be clear on what the article is actually saying.

It is not important whether they are reading it on regular basis, the important things is that they are perfectly capable to read all your data - there is enough evidence for that. Your data is not private anymore if you upload it unencrypted to Dropbox. Whether they actually ever feel the need to browse through it is an entirely different question. Since I do not want to base my data security on beliefs and luck, I encrypt it.

I agree. While Apple provides basic tagging in Photos, we see it (and Google, and now Adobe) using AI to do the necessary analysis on images to make tagging superfluous for most occasions. For those without sophisticated (or neurotic) needs, being able to search ‘blue house’ or ‘puppy’ or ‘Aunt Agatha’ is much better for most people than making them have to manually tag. And I think Apple would not want to change its OS in any way that put more of a burden on the average user, so making tags more systematic and sophisticated is unlikely to be anywhere on a priorities list.

But nothing in that article says that - it says they may reveal your identity to law enforcement if you’re repeatedly sharing copyrighted material and presumably there’s a ECMA takedown order. Again what you say may be true about their encryption but it would be wrong to infer that from the article.

I’m late to this party. But the original post is fantastic – I agree wholeheartedly. I also agree with a lot of the comments. For me, using tags has been tremendously helpful and solved a major problem. I was on PC for a long time and used Evernote. Tagging on Evernote was wonderful because it allowed a note to live in multiple places at the same time. But I preferred using the file system for managing files, and I came to loathe Evernote.

When I moved over to macOs many years ago and discovered that the file system embraced tagging, it allowed me to transition out of Evernote, retain the one feature I really liked, and never look back. Now that I rely on tags and have access to them on iOS, I want the iOS implementation to be rock solid.