Glenn Fleishman
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The “flong” guy: bit.ly/3mh5U0Z for what THAT means. Type historian, Jeopardy champ
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Articles by Glenn Fleishman
Share your location in Messages, now for a custom period
Apple stuffs a lot of different kinds of tasks into Messages. It’s a junk drawer for communications with other people. Send photos? Sure. Set up a safety partner for when you are going somewhere? Why not. Pay somebody? Of course! And, yeah, let’s stick in a poll! But I think the best use beyond text and media of Messages is sharing your location. It’s a convenient way to share your whereabouts with someone else or a group, either indefinitely or for a fixed time period.
AirTag Silencer, Silenced
ElevationLab has withdrawn its AirTag Silencer from sale. The device precisely destroyed the speaker in an AirTag while leaving tracking functions intact. Two weeks ago, I strongly suggested it stop selling it because their precision product offered abusers and stalkers a useful tool—true, available from other sources, but none with the high production quality or the stellar reputation among Apple users that ElevationLab has.
Is your secure iMessage conversation actually secure?
Apple introduced iMessage within Messages in 2011 as its house-brand, end-to-end encrypted messaging product. The promise of iMessage is that posts are always encrypted, using servers and technology developed by Apple and controlled by it. The encryption keys reside on your device, stored so Apple can’t access them, and no third party should ever have the leverage to retrieve them.
Silencing AirTags enables stalkers and domestic violence
ElevationLab has released an AirTag product I find appalling, and I strongly urge they immediately withdraw it from sale and recall all inventory. The AirTag Silencer is a simple device: remove the back panel and battery from an AirTag, position the Silencer’s highly engineered pin over the speaker, tap the pin with a hammer, and the AirTag’s speaker is destroyed. This prevents it from emitting an alert in three circumstances, only one of which is triggered by an owner.
Why Stolen Device Protection makes Passwords safer
After my massive article on migrating your passwords, passkeys, and other secrets from third-party password managers to Apple’s Passwords, Wallet, Safari, and general ecosystem—potentially with help from another app—reader Scott asked whether I was directing people into weaker security. He wrote: If someone manages to steal my device and its passcode, they have access to the contents of my phone, including all of the information stored in Apple Passwords.
See the Behind-the-Scenes Prompts That Power Siri AI
When it comes to our personal information-unlike Liquid Glass-transparency is always better than the alternative. Apple's selling point for Siri AI and Apple Intelligence is that it can use our personal information to answer queries such as "who did I have lunch with during 2025?" and carry out tasks, like creating appointments, building shortcuts, or composing messages.
U.S. small biz can’t ship to the EU anymore
Recent protectionist changes by the European Union further effectively exclude U.S. small businesses like mine from selling to EU customers. It’s a little complicated, but it has to do with how tax and customs fees are collected and extracted from low-value packages. This is not a tariff issue, unbelievably, but one about reducing competition.
Two iPhones? In This Economy? Explaining iPhone Handoff
I'm not a fancy person with a -and sadly, Apple does not send me new iPhones to review. But Apple seems to think I and some reasonable subset of its user base need iPhone Handoff, a new feature in iOS 27 that helps people with two iPhones to swap off using the same phone number by sharing an eSIM. Both iPhones have to share the same Messages, FaceTime, and Apple Account, so I find the use case a little baffling, as I'll explain below.
Migrate to Apple Passwords from your current secret-keeper
You might be interested in knowing how to embrace Apple Passwords with a bear hug, leaving behind your current password manager. If you tried Apple’s Passwords app in the past and were disappointed, you should probably give it another try. The improvements Apple has made in the last couple of releases have brought it to what I consider parity with the most important useful features of well-designed third-party password managers.
Recovery Key storage transition hightlights Apple’s privacy and obscurity
We trust Apple with a lot of our data. In general, that hasn’t seemed like a bad idea; in particular, compared to its competitors, Apple seems to ensure that it can inspect or interact with very little of our data. The company has built its platform and its reputation on being an elegant, frictionless, hands-off conduit.
Preparing for next year’s Rosetta 2 demise
The reckoning is coming. Apple has done it before, and it’s doing it again. After macOS 27 Golden Gate, you will no longer be able to run legacy Intel apps using Rosetta 2. After the 26.4 update in March, when running any affected app in macOS 26 Tahoe, you see a notification banner when you launch affected software or a background component launches that uses Intel code: Support Ending for Intel-based Apps. This version of “[App Name Here]” will not open in a future release of macOS.
MailMaven adds POP, AppleScript, and AI interaction
Back in April of this year, I suggested that the MailMaven email app for macOS might become my new best friend. Months later, with continuous minor and major improvements, the friendship has only grown richer. MailMaven 1.1 in April added POP support for those people who rely on the ancient email mailbox protocol.
Unlock or recover your Mac using a special boot volume
Several years ago, Apple began hiding disk partitions and volumes on the startup drive. The first was a secret volume with a tiny operating system on it that would let you boot from it, after which you could restore from a Time Machine backup, run First Aid in Disk Utility, or reinstall Mac OS X or macOS. Over the years, Apple has multiplied those hidden locations and added more sophistication to what they offer.
When Find My doesn’t help with separation anxiety
I dispense what might be called valuable insight to my friends, as well as in this public forum. My friends know the danger: they might become the topic of a column, which is true for my buddy Jeff, who left a bag containing his passport behind at a hotel. Fortunately, he had an AirTag in his bag. That was, however, just the beginning of the journey. (Jeff gave me permission to share his story.)1 To avoid suspense, I’ll tell you that Jeff doesn’t have his bag back, but will soon.
Pulling the Thread to know if my garage door is closed
I had a simple task that involved Apple Home. If you use Apple Home, you know what happened next. Tears, frustration, the arrival of batteries, paperclips pushed into hard-to-reach holes, many online searches, and—if you are lucky, as I was—success. Siri, am I lazy? My goal was straightforward: can I know if the garage door is open without going to look? Early in the pandemic, we occasionally forgot to close it.
A visit to the App Library: Hiding and deleting apps on iOS
My beloved sister-in-law-in-law (my wife’s brother’s spouse) texted me with an important problem. Her mother had managed to delete the App Store from her Home Screen. How to restore it? While this is a common problem, I realized that the process is completely unintuitive. For her mother’s particular situation, the answer felt like a cheat code for a video game: unlock, swipe left (once or more), search, touch and hold, drag. Done.
My credit card number? Sure! It’s 4242 4242 4242 4242
We live in a modern, jet-set, hyper-fast world! When we want to buy something online, boom, zoom, we use our fingerprint or face to approve the transaction, so we can grab the next Segway outta here! We don’t have time to enter a credit card! And can we trust a webpage form? Pfeh! All right, calm down, 1950s inner voice, it’s not that bad. Most of our transactions involving a payment card or other sensitive data can be safely handled over a secure web connection.
Where we’re going, there are no Maps
Years ago, in the era between the introduction of the iPhone and the modern period of widespread cellular coverage, my wife and I were driving with our quite young children across the vast, unexplored expanse of north-central Pennsylvania, en route to a family wedding. We had plotted out the route and knew where we were going: Eagles Mere, a tiny, former luxury resort town once at the end of a railway line.
Spotlight and iCloud Drive headbang in the CPU mosh pit
I have a Mac Studio M2 Max with 32 GB of RAM and a 1 TB SSD in front of me. While not the most powerful personal computer you can purchase today, it is among the most computationally capable ever made—a vastly capable machine. So why do I have to wait for typing to catch up with me and see a rainbow spinner on the regular? I’ll tell you why: iCloud Drive and Spotlight. Apple lacks any transparency about how iCloud Drive works or fails. The same is true of Spotlight.
Enumerating 264 items in the WWDC fine print Original
Adam Engst at TidBITS took the time to extract every item on the WWDC 2026 keynote slide that captured our attention last week. Even better, Adam grouped the changes into operating systems, apps, and other categories. While the 27 OSes dominate the list with improvements and revisions, you can also note how many changes Apple is making to Photos and Shared Albums, Find My, Music, and a number of other across-the-ecosystem tools.
WWDC 2026: No, Tahoe–yes, Golden Gate
Apple’s pattern of updates is often described as two beats, maybe like the lub-dub sound of your heart: a year of big changes, followed by a year of tweaks that feature just a couple of marquee improvements.1 The 27 series of operating systems marks a big dub year, but there’s a backbeat to the rhythm, too, as Apple retreats from what most of us believe were overreaches in the interface department. Liquid Glass was not beloved.
High Performance mode allows sharing another Mac’s display as if your own
Apple’s built-in screen sharing support for Mac-to-Mac connections has always been a help for those of us with remote setups: headless Macs acting as servers, an office and home Mac, or the laziness of having Macs in different parts of your house you want to access without standing up.1 Under the hood, Apple relies on VNC (Virtual Network Computing), a fairly ancient standard at this point in time, and you probably get the sense of its creaking joints if you use the Screen Sharing app...
I keep spacing out because I’m out of my depth
Have you ever really looked at your Photos, man? There’s much depth there—just keep looking. I’m not stoned; I’m just thinking about Apple’s two ways of demonstrating depth in Photos to simulate adding a sense of layers or dimensionality to images you took with one or more cameras on your iPhone. Starting way back in iOS 16, Apple started analyzing images for your Lock Screen to offer a cool in-front/behind split against the clock. In iOS 26, Apple went further, with Spatial Scene photos.
Orange you glad I didn’t say emoji
I keep finding this old dog can learn new tricks—or, if not quite new, ones that were hiding in plain sight. The other night, using Messages on my iPhone to send a good-night text to my spouse and older child, off on a brief getaway to the coast, I noticed that orange highlighting had invaded my message! I text a couple of friends: “Have you seen this before?” One had not; the other remembered it vaguely, but had no idea why it had occurred.
FileVault keys can’t be escrowed in iCloud anymore
If you’ve enabled FileVault before macOS 26 Tahoe and used the option to escrow your key in iCloud, as of 26.4, you’ll be forced to migrate to a new, better, more secure method. Jason Snell just noted this update in his post about refreshed security. I wrote last September about how Tahoe shifted to storing the last-ditch account Recovery Key in Passwords starting with macOS 26. In that column, I explained, “Your previous choices are preserved.
How I restarted using RSS, and actually noticed!
Recently, I tripped over a headline for an article I wrote for Six Colors in 2015: “How I stopped using RSS and didn’t even notice.” I could hardly remember writing it. But write it I did, at a time when we were deep in a news-aggregation desert. It seemed like RSS had experienced a conceptual death, through neglect and intent. Google first hijacked usage by creating Google Reader during RSS’s heyday in 2005, which sank the market for paid RSS apps and led to near hegemony for Google.
Keeping (and losing) track of Mac sleep settings
Your Mac doesn’t have one kind of sleep—it has several. That fact is generally uninteresting until you find you can’t easily put your Mac into display sleep or system (idle) sleep automatically when you walk away from it or close a laptop’s lid. Let me help you help your Mac drift into the arms of Morpheus by digging beneath the surface. Scattered sleep settings Recently, I got frustrated with this recurrent problem on the Mac in my studio.
Don’t let your Mac’s storage fill up!
Macs don’t do well when they start to approach full storage. The operating system doesn’t provide enough safeguards and backoff options to help you cope with what can become a disaster, requiring a full drive restore! I wrote about this happening with my younger child’s MacBook two years ago. That article was about the abject failure of attempts to get a Mac working after it had reached maximum Mr. Creosote levels. What about avoiding this altogether?
Exploring the wide range of Find My-compatible devices
When the AirTag first shipped five years ago, I glommed right onto writing about it. I already had a section in a book on security and privacy about using the Find My device feature, enabled for iPhones, iPads, Macs, and Apple Watches. I was keyed up to understand where AirTag fit in. Recently, surveying the field, I found a shocking number of Find My network-equipped products, from an inexpensive flashlight to a $3,500 ebike.
MailMaven review: An email nerd’s best friend?
I don’t have a dog for the same reason it’s hard for me to get excited about email apps: the short, sweet lifespans make you love them so intensely and miss them forever when they’re gone. You’re never sure whether you’ll spend several years with a favorite pup or mail client, or get lucky and have 15 or more. Eventually, in my experience with dogs and email clients, they grow old, fade, and are no more. This is the cycle of life and the software business cycle for many apps.
Silence! Listen, here’s how to control sound from your devices
Every Apple device has opinions about when it should make noise. Some of those opinions are reasonable; others will surprise you at 2 a.m.! If you’ve ever wondered why your iPhone alarm blared right through Silent mode, or why your Mac doesn’t have a Silent mode at all, here’s the breakdown. Everything that makes noise Before telling you how to suppress, silence, or control audio output, let’s first look at what might provoke a sound and which settings control whether it’s produced.
Time for your meds, Mr. Fleishman
I have a mostly “love/not-hate” relationship with the Medications feature in the iPhone Health app. Having accrued and had treated a variety of conditions over the years, I found Medications a welcome addition in 2022. You can add drugs you take, the frequency (or as needed), and set them to a schedule. Then you receive a notification at the time you set, plus a reminder. While I’m generally good at “medication adherence,” I’m not perfect.
Stop ghosting me! When ‘Ignore ownership’ is ignored
A powerful tool in the Finder arsenal is a simple checkbox: “Ignore ownership on this volume.” This option appears when you select any locally connected volume on your Mac that isn’t the startup volume and choose File: Get Info. Permissions controls who and, more importantly for this column, what can access data. The Get Info dialog lets you set the option to ignore ownership on non-startup volumes.
AirTag 2 doesn’t break crowdsourcing or anti-stalking measures
After my article on 2nd-generation AirTag compatibility issues a few weeks ago, in which I explained that the 26.2.1 or later release of each of Apple’s operating systems was required to pair and view the revised tracker, my friend Adam Engst posted a question about compatibility, and Six Colors member Scott wrote in with a related query.
Sync your iPhone alarms to an Apple Watch
I’ve written before about the concept of presence. This is the notion that in your digital life, you have many devices—sometimes several near you1—and when you get an alert, a phone call, or other call to action, you do not want every single piece of hardware to chime, shake, or grab you by the scruff of your neck.2 And yet. And yet. When you desperately want the digital jingle bell to sound off on a particular device, my goodness, what a fuss that might be.
Buying new AirTags? Check your compatibility first.
Apple’s newly updated AirTag model, informally called an AirTag 2 but just an “AirTag” to Apple, has a greater Bluetooth range, offers greater Precision Finding with newer iPhones, works with newer Apple Watch models, and produces sound Apple states is 50% louder than the original. The new AirTag has improved range and produces louder sounds, but requires careful consideration of backwards compatibility. Consult its reverse side for obscure markings.
Why your Mac’s Phone app can’t hear you
Is it age? Obliviousness? A delayed mental unacuity from my heart surgery last November? Or could it be a Shazaam/Berenstain Bears scenario? All I know is that the first version of this article took Apple to task for including a menu in the Phone app for macOS 26 Tahoe that, in fact, was there all along. Or was it?1 The Phone app introduced in Tahoe for the Mac (and on iPadOS 26) made it much easier to deal with telephony across your devices.
Why AutoFill Cards sync and Apple Pay cards don’t
Apple lets you store payment cards in two places on your devices. Apple Pay is for point-of-sale (POS) transactions at a payment terminal or the like, as well as for payments in apps or in Safari. AutoFill Cards, the name of the menu items, lets you, er, automatically fill cards within Safari, and in any browser that supports Apple’s autofill framework. Why does Apple have two places to store credit and debit cards? Why is the way you set them up similar, but not identical?
Remove the RAW photo from a RAW+JPEG pair
Six Colors subscriber Mihir writes in with a Photos question: How do I delete just the RAW file in a RAW+JPEG pair from my photos library on my iPad or my iPhone? The short answer: you can’t. Not directly, anyway. And it’s not just an iOS or iPadOS limitation—macOS won’t let you do it either. I can understand why Mihir asks. An image in RAW format can occupy several times the amount of storage as a JPEG equivalent. This has to do with the nature of the image being stored, as I explain below.
POP goes the email: migrate to IMAP
Some of us are old enough to remember using pine and other Unix screen-based email readers. Younger folks might have cut their teeth on Eudora and other Mac apps (back when we called them “software programs”) that could seamlessly log into a mail server, retrieve email locally, and let us interact with it. The first widely successful protocol of that type was Post Office Protocol (POP).1 POP’s job was to download mail. If you left it on the server, it was just a giant mailbox.
Messages craves cloud syncing, even when you don’t want it
Apple added iCloud for Messages several years ago to solve the problem of presence.1 Presence is a loose concept that describes where you are active at a given moment when some kind of alert or information should reach you. For instance, Apple’s awareness of which device you’re actively using should prevent an incoming phone call from ringing on several devices at once. (Spoiler: It does not.) With Messages in iCloud enabled, all messages from this device and from other enabled devices sync.
You spin me right round (like a Wi-Fi identifier)
It seems like everyone—hackers, governments, corporations—want to track everything we do online and in the physical world. Apple has a multi-year history of rolling out new methods of deflecting, deterring, or blocking new forms of unwanted tracking. One that may have slipped under your radar could affect how your devices connect and stay connected over Wi-Fi at your home or office and while using hotspots on the ground or in the air.
It’s pronounced “Throat Warbler Mangrove,” Siri
Siri can be frustrating. And we know from the most recent Apple financials call that Tim “This is Tim” Cook thinks so, too, even if he would intentionally not state that.
Soaping up Liquid Glass: less transparency, more contrast
For those who find the fall 2025 Liquid Glass interface that Apple applied to all its operating systems a bit much—too transparent, too shiny, too hard to read or interpret stuff through layers—Apple introduced a new option in its 26.1 releases in early November to dial things back. This choice can bump down the glassification of Apple’s interfaces.
Why does my device stick to the wrong Wi-Fi router?
You may never have heard the term Extended Service Set Identifier (ESSID), and why should you have? It’s a mildly esoteric term in the Wi-Fi world for how multiple routers with the same name form an extended network. In fact, it’s not even a protocol; it’s just a name, which makes it even more confusing. So why would I bring it up?
Can’t autosave? A cloud might be in the way
Your Mac mostly hides its Unix1 underbelly. You can tap into it as you need, but it mainly drives the system. For many people—perhaps most—the Unix part crops up when you’re dealing with permissions. Permissions refers to the access that files and folders (directories) allow with respect to specific registered users, groups, and special system roles. My friend Larry, whom I previously helped delete his email account, had a perplexing permissions problem.
Making a Scene: When Apple Home gave me lemons, I went bananas
You might wonder why I have an Apple Home scene called Banana Room and another called Lemon Room. I wonder this, too. It all started late last year, as we planned to be away from home for a few weeks, and thought it was a good time to test automation and smart devices. We have had a very slow household adoption of such, and stick to HomeKit-compatible devices. Our thermostats were HomeKit-connected, as were a couple of smart bulbs.
Mail rules run amok!
A friend of mine, Larry, asked for a little help with some various email and sync problems. On a Zoom call with him, I diagnosed it, helped him find the correct settings, and then we promptly deleted his email account and all his thousands of stored messages. (There’s a twist at the end.) Let’s rewind. Larry encountered something I’ve seen many times over the last couple of decades, including inflicting it on myself.
Slam Mac windows shut without saving
When I was in college, a friend told me about working a summer job at one of those art stores that sold extremely average factory-produced oil paintings that were designed to fit people’s decor.1 They probably made most of their money from the markup on frames. The FileMaker Pro database used to manage sales and inventory was finicky. Once, it crashed on my friend, and her boss was not happy about it.
How to tell what’s playing audio on your Mac
My friend and editor Joe and I were trying to talk.1 But something on his end continued to produce sound, and he couldn’t tell what it was. After some exploration, he realized that we had started using Slack’s “huddle” feature for a one-to-one audio chat and switched to FaceTime. He hadn’t hung up in Slack, and it was playing goshdarned hold music. He said, “Shouldn’t there be a way to figure out which app is producing sound?” I said, yes—and then couldn’t immediately determine how.
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