I was reading Macintosh Human Interface Guidelines from 1992 and found this nice illustration:

accompanied by explanation:

Fast forward to 2025. Apple releases macOS Tahoe. Main attraction? Adding unpleasant, distracting, illegible, messy, cluttered, confusing, frustrating icons (their words, not mine!) to every menu item:

It’s bad. But why exactly is it bad? Let’s delve into it!

Disclaimer: screenshots are a mix from macOS 26.1 and 26.2, taken from stock Apple apps only that come pre-installed with the system. No system settings were modified.

Icons should differentiate

The main function of an icon is to help you find what you are looking for faster.

Perhaps counter-intuitively, adding an icon to everything is exactly the wrong thing to do. To stand out, things need to be different. But if everything has an icon, nothing stands out.

The same applies to color: black-and-white icons look clean, but they don’t help you find things faster!

Microsoft used to know this:

Look how much faster you can find Save or Share in the right variant:

It also looks cleaner. Less cluttered.

A colored version would be even better (clearer separation of text from icon, faster to find):

I know you won’t like how it looks. I don’t like it either. These icons are hard to work with. You’ll have to actually design for color to look nice. But the principle stands: it is way easier to use.

Consistency between apps

If you want icons to work, they need to be consistent. I need to be able to learn what to look for.

For example, I see a “Cut” command and next to it. Okay, I think. Next time I’m looking for “Cut,” I might save some time and start looking for instead.

How is Tahoe doing on that front? I present to you: Fifty Shades of “New”:

I even collected them all together, so the absurdity of the situation is more obvious.

Granted, some of them are different operations, so they have different icons. I guess creating a smart folder is different from creating a journal entry. But this?

Or this:

Or this:

There is no excuse.

Same deal with open:

Save:

Yes. One of them is a checkmark. And they can’t even agree on the direction of an arrow!

Close:

Find (which is sometimes called Search, and sometimes Filter):

Delete (from Cut-Copy-Paste-Delete fame):

Minimize window.

These are not some obscure, unique operations. These are OS basics, these are foundational. Every app has them, and they are always in the same place. They shouldn’t look different!

Consistency inside the same app

Icons are also used in toolbars. Conceptually, operations in a toolbar are identical to operations called through the menu, and thus should use the same icons. That’s the simplest case to implement: inside the same app, often on the same screen. How hard can it be to stay consistent?

Preview:

Photos: same and mismatch, but reversed ¯\_(ツ)_/¯

Maps and others often use different symbols for zoom:

Icon reuse

Another cardinal sin is to use the same icon for different actions. Imagine: I have learned that means “New”:

Then I open an app and see. “Cool”, I think, “I already know what it means”:

Gotcha!

You’d think: okay, means quick look:

Sometimes, sure. Some other times, means “Show completed”:

Sometimes is “Import”:

Sometimes is “Updates”:

Same as with consistency, icon reuse doesn’t only happen between apps. Sometimes you see in a toolbar:

Then go to the menu in the same app and see means something else:

Sometimes identical icons meet in the same menu.

Sometimes next to each other.

Sometimes they put an entire barrage of identical icons in a row:

This doesn’t help anyone. No user will find a menu item faster or will understand the function better if all icons are the same.

The worst case of icon reuse so far has been the Photos app:

It feels like the person tasked with choosing a unique icon for every menu item just ran out of ideas.

Understandable.

Too much nuance

When looking at icons, we usually allow for slight differences in execution. That lets us, for example, understand that these technically different road signs mean the same thing:

Same applies for icons: if you draw an arrow going out of the box in one place and also an arrow and the box but at a slightly different angle, or with different stroke width, or make one filled, we will understand them as meaning the same thing.

Like, is supposed to mean something else from ? Come on!

Or two-letter As that only slightly differ in the font size:

A pencil is “Rename” but a slightly thicker pencil is “Highlight”?

Arrows that use different diagonals?

Three dots occupying ⅔ of space vs three dots occupying everything. Seriously?

Slightly darker dots?

The sheet of paper that changes meaning depending on if its corner is folded or if there are lines inside?

But the final boss are arrows. They are all different:

Supposedly, a user must become an expert at noticing how squished the circle is, if it starts top to right or bottom to right, and how far the arrow’s end goes.

Do I care? Honestly, no. I could’ve given it a shot, maybe, if Apple applied these consistently. But Apple considers and to mean the same thing in one place, and expects me to notice minute details like this in another?

Sorry, I can’t trust you. Not after everything I’ve seen.

Detalization

Icons are supposed to be easily recognizable from a distance. Every icon designer knows: small details are no-go. You can have them sometimes, maybe, for aesthetic purposes, but you can’t rely on them.

And icons in Tahoe menus are tiny. Most of them fit in a 12×12 pixel square (actual resolution is 24×24 because of Retina), and because many of them are not square, one dimension is usually even less than 12.

It’s not a lot of space to work with! Even Windows 95 had 16×16 icons. If we take the typical DPI of that era at 72 dots per inch, we get a physical icon size of 0.22 inches (5.6 mm). On a modern MacBook Pro with 254 DPI, Tahoe’s 24×24 icons are 0.09 inches (2.4 mm). Sure, 24 is bigger than 16, but in reality, these icons’ area is 4 times as small!

So when I see this:

I struggle. I can tell they are different. But I definitely struggle to tell what’s being drawn.

Even zoomed in 20×, it’s still a mess:

Or here. These are three different icons:

Am I supposed to tell plus sign from sparkle here?

Some of these lines are half the pixel thicker than the other lines, and that’s supposed to be the main point:

Is this supposed to be an arrow?

A paintbrush?

Look, a tiny camera.

It even got an even tinier viewfinder, which you can almost see if you zoom in 20×:

Or here. There is a box, inside that box is a circle, and inside it is a tiny letter. i with a total height of 2 pixels:

Don’t see it?

I don’t. But it’s there...

And this is a window! It even has traffic lights! How adorable:

Remember: these are retina pixels, ¼ of a real pixel. Steve Jobs himself claimed they were invisible.

It turns out there’s a magic number right around 300 pixels per inch, that when you hold something around to 10 to 12 inches away from your eyes, is the limit of the human retina to differentiate the pixels.

And yet, Tahoe icons rely on you being able to see them.

Pixel grid

When you have so little space to work with, every pixel matters. You can make a good icon, but you have to choose your pixels very carefully.

For Tahoe icons, Apple decided to use vector fonts instead of good old-fashioned bitmaps. It saves Apple resources—draw once, use everywhere. Any size, any display resolution, any font width.

But there’re downsides: fonts are hard to position vertically, their size doesn’t map directly to pixels, stroke width doesn’t map 1-to-1 to pixel grid, etc. So, they work everywhere, but they also look blurry and mediocre everywhere:

They certainly start to work better once you give them more pixels.

or make graphics simpler. But the combination of small details and tiny icon size is deadly. So, until Apple releases MacBooks with 380+ DPI, unfortunately, we still have to care about the pixel grid.

Confusing metaphors

Icons might serve another function: to help users understand the meaning of the command.

For example, once you know the context (move window), these icons explain what’s going on faster than words:

But for this to work, the user must understand what’s drawn on the icon. It must be a familiar object with a clear translation to computer action (like Trash can → Delete), a widely used symbol, or an easy-to-understand diagram. HIG:

A rookie mistake would be to misrepresent the object. For example, this is how selection looks like:

But its icon looks like this:

Honestly, I’ve been writing this essay for a week, and I still have zero ideas why it looks like that. There’s an object that looks like this, but it’s a text block in Freeform/Preview:

It’s called character.textbox in SF Symbols:

Why did it become a metaphor for “Select all”? My best guess is it’s a mistake.

Another place uses text selection from iOS as a metaphor. On a Mac!

Some concepts have obvious or well-established metaphors. In that case, it’s a mistake not to use them. For example, bookmarks: . Apple, for some reason, went with a book:

Sometimes you already have an interface element and can use it for an icon. However, try not to confuse your users. Dots in a rectangle look like password input, not permissions:

Icon here says “Check” but the action is “Uncheck”.

Terrible mistake: icon doesn’t help, it actively confuses the user.

It’s also tempting to construct a two-level icon: an object and some sort of indicator. Like, a checkbox and a cross, meaning “Delete checkbox”:

Or a user and a checkmark, like “Check the user”:

Unfortunately, constructs like this rarely work. Users don’t build sentences from building blocks you provide; they have no desire to solve these puzzles.

Finding metaphors is hard. Nouns are easier than verbs, and menu items are mostly verbs. How does open look? Like an arrow pointing to the top right? Why?

I’m not saying there’s an obvious metaphor for “Open” Apple missed. There isn’t. But that’s the point: if you can’t find a good metaphor, using no icon is better than using a bad, confusing, or nonsensical icon.

There’s a game I like to play to test the quality of the metaphor. Remove the labels and try to guess the meaning. Give it a try:

It’s delusional to think that there’s a good icon for every action if you think hard enough. There isn’t. It’s a lost battle from the start. No amount of money or “management decisions” is going to change that. The problems are 100% self-inflicted.

All this being said, I gotta give Apple credit where credit is due. When they are good at choosing metaphors, they are good:

Symmetrical actions

A special case of a confusing metaphor is using different metaphors for actions that are direct opposites of one another. Like Undo/Redo, Open/Close, Left/Right.

It’s good when their icons use the same metaphor:

Because it saves you time and cognitive resources. Learn one, get another one for free.

Because of that, it’s a mistake not to use common metaphors for related actions:

Or here:

Another mistake is to create symmetry where there is none. “Back” and “See all”?

Some menus in Tahoe make both mistakes. E.g. lack of symmetry between Show/Hide and false symmetry between completed/subtasks:

Import not mirrored by Export but by Share:

Text in icons

HIG again:

Authors of HIG are arguing against including text as a part of an icon. So something like this:

or this:

would not fly in 1992.

I agree, but Tahoe has more serious problems: icons consisting only of text. Like this:

It’s unclear where “metaphorical, abstract icon text that is not supposed to be read literally” ends and actual text starts. They use the same font, the same color, so how am I supposed to differentiate? Icons just get in a way: A...Complete? AaFont? What does it mean?

I can maybe understand and . Dots are supposed to represent something. I can imagine thinking that led to . But ? No decorations. No effects. Just plain Abc. Really?

Text transformations

One might think that using icons to illustrate text transformations is a better idea.

Like, you look at this:

or this:

or this:

and just from the icon alone understand what will happen with the text. Icon illustrates the action.

Also, BIU are well-established in word processing, so all upside?

Not exactly. The problem is the same—text icon looks like text, not icon. Plus, these icons are excessive. What’s the point of taking the first letter and repeating it? The word “Bold” already starts with a letter “B”, it reads just as easily, so why double it? Look at it again:

It’s also repeated once more as a shortcut...

There is a better way to design this menu:

And it was known to Apple for at least 33 years.

System elements in icons

Operating system, of course, uses some visual elements for its own purposes. Like window controls, resize handles, cursors, shortcuts, etc. It would be a mistake to use those in icons.

Unfortunately, Apple fell into this trap, too. They reused arrows.

Key shortcuts:

HIG has an entire section on ellipsis specifically and how dangerous it is to use it anywhere else in the menu.

And this exact problem is in Tahoe, too.

Icons break scanning

Without icons, you can just scan the menu from top to bottom, reading only the first letters. Because they all align:

In Tahoe, though, some menu items have icons, some don’t, and they are aligned differently:

Some items can have both checkmarks and icons, or have only one of them, or have neither, so we get situations like this:

Ugh.

Special mention

This menu deserves its own category:

Same icon for different actions. Missing the obvious metaphor. Somehow making the first one slightly smaller than the second and third. Congratulations! It got it all.

Is HIG still relevant?

I’ve been mentioning HIG a lot, and you might be wondering: is an interface manual from 1992 still relevant today? Haven’t computers changed so much that entirely new principles, designs, and idioms apply?

Yes and no. Of course, advice on how to adapt your icons to black-and-white displays is obsolete. But the principles—as long as they are good principles—still apply, because they are based on how humans work, not how computers work.

Humans don’t get a new release every year. Our memory doesn’t double. Our eyesight doesn’t become sharper. Attention works the same way it always has. Visual recognition, motor skills—all of this is exactly as it was in 1992.

So yeah, until we get a direct chip-to-brain interface, HIG will stay relevant.

Conclusion

In my opinion, Apple took on an impossible task: to add an icon to every menu item. There are just not enough good metaphors to do something like that.

But even if there were, the premise itself is questionable: if everything has an icon, it doesn’t mean users will find what they are looking for faster.

And even if the premise was solid, I still wish I could say: they did the best they could, given the goal. But that’s not true either: they did a poor job consistently applying the metaphors and designing the icons themselves.

I hope this article would be helpful in avoiding common mistakes in icon design, which Apple managed to collect all in one OS release. I love computers, I love interfaces, I love visual communication. It makes me sad seeing perfectly good knowledge already accessible 30 years ago being completely ignored or thrown away today.

On the upside: it’s not that hard anymore to design better than Apple! Let’s drink to that. Happy New year!

Notes

During review of this post I was made familiar with Jim Nielsen’s article, which hits a lot of the same points as I do. I take that as a sign there’s some common truth behind our reasoning.

Also note: Safari → File menu got worse since 26.0. Used to have only 4 icons, now it’s 18!

Thanks Kevin, Ryan, and Nicki for reading drafts of this post.

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Anthropic let its Claude AI run a vending machine in the Wall Street Journal newsroom for three weeks as part of an internal stress test called Project Vend, and the experiment ended in financial ruin after journalists systematically manipulated the bot into giving away its entire inventory for free. The AI, nicknamed Claudius, was programmed to order inventory, set prices, and respond to customer requests via Slack. It had a $1,000 starting balance and autonomy to make individual purchases up to $80. Within days, WSJ reporters had convinced it to declare an "Ultra-Capitalist Free-for-All" that dropped all prices to zero. The bot also approved purchases of a PlayStation 5, a live betta fish, and bottles of Manischewitz wine -- all subsequently given away. The business ended more than $1,000 in the red. Anthropic introduced a second version featuring a separate "CEO" bot named Seymour Cash to supervise Claudius. Reporters staged a fake boardroom coup using fabricated PDF documents, and both AI agents accepted the forged corporate governance materials as legitimate. Logan Graham, head of Anthropic's Frontier Red Team, said the chaos represented a road map for improvement rather than failure.

Read more of this story at Slashdot.

A man in Atlanta has been arrested and charged for allegedly deleting data from a Google Pixel phone before a member of a secretive Customs and Border Protection (CBP) unit was able to search it, according to court records and social media posts reviewed by 404 Media. The man, Samuel Tunick, is described as a local Atlanta activist in Instagram and other posts discussing the case.

The exact circumstances around the search—such as why CBP wanted to search the phone in the first place—are not known. But it is uncommon to see someone charged specifically for wiping a phone, a feature that is easily accessible in some privacy and security-focused devices.

The indictment says on January 24, Tunick “did knowingly destroy, damage, waste, dispose of, and otherwise take any action to delete the digital contents of a Google Pixel cellular phone, for the purpose of preventing and impairing the Government’s lawful authority to take said property into its custody and control.” The indictment itself was filed in mid-November.

Tunick was arrested earlier this month, according to a post on a crowd-funding site and court records. “Samuel Tunick, an Atlanta-based activist, Oberlin graduate, and beloved musician, was arrested by the DHS and FBI yesterday around 6pm EST. Tunick's friends describe him as an approachable, empathetic person who is always finding ways to improve the lives of the people around him,” the site says. Various activists have since shared news of Tunick’s arrest on social media.

The indictment says the phone search was supposed to be performed by a supervisory officer from a CBP Tactical Terrorism Response Team. The American Civil Liberties Union (ACLU) wrote in 2023 these are “highly secretive units deployed at U.S. ports of entry, which target, detain, search, and interrogate innocent travelers.” 

“These units, which may target travelers on the basis of officer ‘instincts.’ raise the risk that CBP is engaging in unlawful profiling or interfering with the First Amendment-protected activity of travelers,” the ACLU added. The Intercept previously covered the case of a sculptor and installation artist who was detained at San Francisco International Airport and had his phone searched. The report said Gach did not know why, even years later. 

Court records show authorities have since released Tunick, and that he is restricted from leaving the Northern District of Georgia as the case continues.

The prosecutor listed on the docket did not respond to a request for comment. The docket did not list a lawyer representing Tunick.

Presidents have always sent people to lead the Pentagon who respect the institutions and personnel of the armed forces, not least because Americans tend to bristle at any sign that an administration does not unreservedly support the men and women of the U.S. military. (Just ask Bill Clinton and Barack Obama, both of whom were castigated for such supposed disrespect.) In his first term, Donald Trump sent General James Mattis, a veteran of wars in Iraq and Afghanistan, and then, when Mattis quit, he appointed a long-serving defense professional, Mark Esper.

But this time, the president found a perfect instrument of destruction to send across the Potomac: Pete Hegseth, a Trump sycophant who served in the military, topped out at the mid-level rank of major, and left full of bitterness and resentment toward a military establishment that clearly didn’t value his brilliance and fortitude.

The halls of the Pentagon are apparently strewn with rakes these days, and Hegseth has managed to step on almost all of them, including security blunders, needless fights with the press, and envious, unmanly whining about the medals on the uniform of Senator Mark Kelly, a veteran of higher rank and far greater achievement than Hegseth himself. Like Trump, Hegseth thinks his job is to get even with people he views as enemies: When Hegseth pulled more than 800 senior officers into an auditorium to give them a long and pointless harangue, it was not only disrespectful; it was cringe-inducing, like watching the angriest kid in your high school come back 20 years later as the principal and unload his adolescent gripes on all the teachers in the staff lounge.

[Read: Holy warrior]

Now, however, Hegseth is in new and far more dangerous territory. The Washington Post reported last Friday that, back in September, Hegseth ordered the killing of the survivors of the first strike against what the administration says are terrorist-controlled drug boats. If this report is accurate, it means that Hegseth issued what is called a “no quarter” order, a crime in both American and international law.

So far, the president and the secretary have not disputed the facts, instead fumbling about with classic Beltway-style “non-denial denials.” Today, the White House admitted that the second strike did in fact take place, but on the orders of the Special Operations Command chief, Admiral Frank Bradley, which seems to be setting Bradley up as a scapegoat. White House Press Secretary Karoline Leavitt said today that “Hegseth authorized Admiral Bradley to conduct these kinetic strikes,” adding that Bradley “worked well within his authority and the law directing the engagement to ensure the boat was destroyed and the threat to the United States of America was eliminated.”

This seems implausible. Bradley is an experienced officer who by virtue of his rank and position would be intimately familiar with the laws of armed conflict. He would have to know that such an order is likely a war crime, and any senior officer would want civilian leadership to sign off on an order with such potentially immense consequences, especially on the first such operation. (If the admiral actually did give the order on his own, that’s little comfort; it would mean Hegseth’s Defense Department is even more dysfunctional and out of control than anyone might have guessed.)

If either Hegseth or Bradley gave such an order—or if Hegseth issued the order and Bradley carried it out—both could be guilty of murder and war crimes. The United States, after World War II, prosecuted German and Japanese officers for similar offenses. (Yesterday, in fact, was the 80th anniversary of the execution by firing squad of Heinz-Wilhelm Eck, a Nazi U-Boat commander who sank a civilian steamer and then killed the survivors.) Such a possibility is horrendous enough, but Hegseth has since responded to these grave accusations with the crass juvenility characteristic of the toddlers who run this administration.

Yesterday, the secretary of defense of the United States of America posted a meme on X depicting Franklin, the cartoon turtle who is a beloved children’s-book character, as a Special Forces operator killing people on boats. He added a comment: “For your Christmas wish list…” Just to make the point, the secretary tagged the X account of SOUTHCOM, the Southern Forces Command, which has had to carry out the strikes, as if blowing up boats and killing the survivors was a joke to be shared with a chuckle and a backslap.

Perhaps Hegseth thinks that sinking boats on the high seas is funny. Maybe he just wanted to own the libs and all that. Or maybe he thought he could disrupt the gathering war-crimes narrative, like the school delinquent pulling a fire alarm during an exam. Or maybe he just has poor judgment and even worse impulse control (which would explain a lot of things about Pete Hegseth). No matter the reason, his choice to trivialize the use of American military force reveals both the shallowness of the man’s character and the depth of his contempt for the military as an institution.

Posting stupid memes after being accused of murder is not the response of a patriot who must answer to the public about the security of the United States and its people in uniform. It is not the response of a secretary of defense who values the advice of the officers who report to him. It is not the response of a human being who comprehends the risks—and the costs—of ordering other people to kill helpless men clinging to the wreck of a boat.

It is, instead, the response of a sneering, spoiled punk who has been caught doing wrong and is now daring the local fuzz to take him in and risk the anger of his rich dad—a role fulfilled by Donald Trump, in this case.

Institutions, for a time, can cope with buffoonish leaders. While the secretary has been festooning the Pentagon with new Department of War signs, adults in the building have tried to conduct some of the nation’s geopolitical business. Secretary of the Army Daniel Driscoll, for example, is likely the Defense Department point man for Ukraine because Hegseth has made a fool of himself too many times to be taken seriously by American opponents. (The Russians would have to suppress the smirks on their faces if Hegseth were sent to Moscow or Geneva for anything more than a grip-and-grin photo opportunity.)

But Hegseth is still the secretary of defense. He can be kept out of important meetings and excluded from rooms where policies are being debated, but his authority to order the military into action means he can still risk American lives and get people killed. In a remarkable paradox, Hegseth’s formal power and personal incompetence—to say nothing of his apparently nonexistent moral compass—mean he remains dangerous even if he is otherwise insignificant.

[Read: 20 U.S. boat strikes in three months]

Enough of this. Trump is president and has the right to stay in office for his term, even if he thinks fallen warriors are “losers” and “suckers” who have no purpose beyond serving his needs as props and pawns. He again showed how little he regards military lives this weekend when he was asked if he would attend the funeral of Sarah Beckstrom, the young West Virginia National Guardsman killed in Washington, D.C., last week. He said he would think about it, and then immediately made her death about him by adding that he won big in West Virginia in the last election, as if that were relevant to whether he owed her his presence at her funeral.

Pete Hegseth, however, was elected by no one. He is an unprofessional—and sometimes unstable—appointee who does not seem to comprehend the seriousness of the office he occupies, does not respect the senior officers who serve this country, and does not seem to care at all about the people of the U.S. military, except that he’s worried that too many of them are fat—or women. Hegseth is unqualified and incompetent, and he should have been fired months ago.

The secretary is unlikely to resign, but Trump has a record of throwing people under the bus when they are no longer of use to him, and Republicans should increase the pressure on him to fire the most unqualified secretary of defense in U.S. history. Let them and all Americans say to Hegseth what the British politician Leo Amery said to Neville Chamberlain as Europe began to crumble under the Nazi offensive in 1940: “Depart, I say, and let us have done with you.” Channeling Oliver Cromwell from centuries earlier, Amery added: “In the name of God, go.”

In the name of God, Pete Hegseth, go.

She's not a big fan of electric cars and solar energy, but she does like coal: Diana Furchtgott-Roth wrote the blueprint for Trump's energy policy in "Project 2025." DER SPIEGEL wanted to know more about how the Heritage Foundation strategist thinks.