From Tidbits by way of Jim H
Sometimes life’s detours teach us unexpected lessons. Adam Engst shares how a cycling accident and a broken bone in his wrist forced him to rely on iOS 27’s improved dictation and macOS Voice Control—and how he discovered both their impressive capabilities and frustrating limitations. While convalescing, he found time to document the quirks of setting up a new iPhone 18 Pro and Apple Watch Series 12, including eSIM transfers, Google Account chaos, and Apple Pay verification headaches. For those exploring Apple’s AI assistant, Adam highlights David Pogue’s extensive testing of Siri AI with 125 real-world prompts and invites readers to crowdsource their own hits and misses. Glenn Fleishman rounds out the issue by explaining iPhone Handoff, the new iOS 27 feature that lets you share an eSIM between two iPhones—useful for a few, seemingly irrelevant for most. Notable Mac app releases this week include Carbon Copy Cloner 7.2, ChronoSync 12.0.3, Evernote 11.34.8, Fantastical 4.2 and Cardhop 2.5, OmniFocus 4.9, OmniOutliner 6.3, and PowerPhotos 3.4.7.
Siri AI Hits and MissesWhat a Broken Wrist Taught Me About iOS 27 Dictation and macOS Voice ControlNotes on Setting Up a New iPhone 18 Pro and Apple Watch Series 12Two iPhones? In This Economy? Explaining iPhone HandoffWatchlist: Mac App UpdatesCarbon Copy Cloner 7.2ChronoSync 12.0.3Evernote 11.34.8Fantastical 4.2 and Cardhop 2.5OmniFocus 4.9OmniOutliner Essentials and Pro 6.3PowerPhotos 3.4.7
ADAM ENGST 17 September 2026
Siri AI Hits and Misses
In 125 Tests of the New AI Siri, David Pogue has done the yeoman’s work of testing not just a few Siri AI requests but a whopping 125 across the categories of personal information, phone and app control, Internet queries, visual intelligence, and screen intelligence. He shares each request, briefly explains how Siri responded, and notes whether or not it succeeded. Many of his examples won’t apply directly to your situation, of course, but they give you a sense of what you can accomplish with Siri AI.
For those who are using OS 27 and have gotten into the Siri AI beta, let’s crowdsource our own list of Siri AI hits and misses in the comments below. Follow Pogue’s example of starting successful prompts with ✅ and unsuccessful ones with ❌. You decide whether partial success gets a ✅ or an ❌, perhaps based on how close it came or whether a follow-up made it work. Let’s also use ⏳ to indicate prompts that worked but took so long that it wasn’t worth having Siri do it for you. Please remove any sensitive information before posting.
ADAM ENGST 21 September 2026
What a Broken Wrist Taught Me About iOS 27 Dictation and macOS Voice Control
There is a saying in the disability world that we are all only temporarily able-bodied. No matter who you are, no matter how healthy or capable you are now, there will come a time when you will need the kinds of accommodations that disability advocates have fought for over the years. Whether it’s due to genetics, accident, or inevitable aging, we will all have problems with vision, hearing, mobility, and motor control. Here’s my story.
On 15 September 2026, I started a planned 45-mile ride on my ElliptiGO when, just 0.5 miles in, I crashed on a flat, smooth suburban road with no traffic. I have no recollection of what caused me to go down, but I hit the left side of my head, cracking my helmet, strained muscles in my left hand, fractured the scaphoid bone in my right wrist, and picked up discrete points of road rash on my left ankle, knee, hip, chest, and elbow, plus all down the center of my face: forehead, nose, upper lip, and chin. At least I didn’t damage the tooth implants in three of my front teeth, which had been installed two days earlier after a 19-month process following a February 2025 skating accident.
Some passersby helped me immediately, and good friends who lived around the corner came and got me while Tonya was en route from home. Once she arrived, she took me to the ER, where a CT scan showed no problems (apart from the usual bats in the belfry), but X-rays revealed the broken wrist bone—luckily, a non-displaced fracture of the distal pole of the scaphoid bone, which is apparently the most common and heals quickly and successfully. They cleaned me up and sent me home.
Since then, although the road rash was ultimately minor, if a little visually shocking for a few days, I’ve had quite a lot of pain when using my left hand, and the right hand has either been in a temporary brace (which I was told not to take off but which was extremely painful, cutting off most sensation in my thumb) or in a (much more comfortable) cast. My ability to grip and lift objects has been severely curtailed, leading to exciting new explorations in personal care and marital patience! Unsurprisingly, due to the head trauma (the ER doctor never used the word concussion), I have been quite fatigued and spending a lot of the day in bed, resting, listening to an audiobook, or reading a book, depending on what I feel up to.
Needless to say, I haven’t been nearly as productive work-wise as I normally am. Happily, Glenn Fleishman contributed an article right away, and I have been able to get some work done using iOS 27’s dictation and macOS 27’s Golden Gate Voice Control. And that has provided a whole world of interesting results.
iOS 27 Dictation Now Supports Text Editing
The most useful discovery is that Apple has significantly improved dictation in iOS 27 by adding a few capabilities for editing text from the Voice Control system. In other words, Apple has finally done some of the things I requested in “How iOS and macOS Dictation Can Learn from Voice Control’s Dictation” (31 August 2020). Remember, dictation is what you get when you tap the microphone button on the keyboard, while Voice Control is an all-encompassing system that you turn on in Settings > Accessibility > Voice Control. The problem with leaving Voice Control on permanently is that it’s constantly listening and thus inserting text when you don’t want that, and at times I have felt that its dictation isn’t as good.
Most notably, when you’re using iOS’s regular dictation, you can now change the case of words and phrases by saying “Capitalize phrase” or “Lowercase phrase.” Incorrect capitalization of words drives me up the wall. Equally useful is the ability to fix misheard or misspoken words by saying “Replace phrase with phrase.” Most other Voice Control commands aren’t available in dictation, but you can say “Select phrase” and “Undo that.”
So if you use dictation in Messages a lot, as I do, I strongly encourage you to update iOS 27 and start practicing with the capitalization and replacement commands. They are really useful.
Relying on macOS 27 Voice Control
Unfortunately, while Apple added some of Voice Control’s capabilities to dictation in iOS 27, it didn’t extend that effort to macOS 27 Golden Gate. Put simply, when you use dictation in macOS, you don’t have access to any text-editing commands.
Once I came to that sad realization, I turned on Voice Control in System Settings > Accessibility > Voice Control, and I have been doing pretty much everything on my Mac through Voice Control’s dictation since then. I have no trouble using my MacBook Pro’s trackpad for basic mousing and clicking (dragging long distances is hard; I’m experimenting with Drag Lock), and I can press individual keys on the keyboard, but I can’t type comfortably or accurately because of the pain in my left hand and my right hand’s restricted motion from the cast.
Overall, Voice Control dictation has worked extremely well, thanks in large part to Grammarly (see “Why Grammarly Beats Apple’s Writing Tools for Serious Writers,” 30 January 2025). Although macOS often recognizes words incorrectly, such as the original “enlarge” in the previous sentence, Grammarly does an excellent job of figuring out what I intended to say and offering a correction for either just the word (left) or for multiple words in the sentence (right).
You might wonder why I don’t use one of the many AI-powered dictation apps. The simple reason is that they all require you to talk for a while, then transcribe and process the audio before pasting the text back into wherever you’re writing. Even though it’s quick, it doesn’t work for me because I don’t know what I’m going to say until I have seen what I’ve already said, even as I’m writing a sentence. Plus, I frequently go back and tweak wording in sentences I’ve just written—I need word-level dictation for editing. For instance, when writing that last clause, I started with “per-word dictation” but decided I didn’t like it as soon as I saw it and added “for editing” after the fact.
That doesn’t mean Voice Control’s dictation is ideal. It frequently confuses plurals and possessives, not to mention homonyms; it can’t quote text to save its life; it is seemingly incapable of entering an em dash instead of an en dash; and even though I can add special words to its vocabulary, it often fails to recognize them, such that I regularly get “elliptical” instead of the desired “ElliptiGO.” Grammarly can fix only so many of these mistakes.
More annoyingly, Voice Control doesn’t work reliably across all apps. For instance, I can’t get it to capitalize a specific word in Slack, although I can select some text and say “Capitalize that.” It also can’t replace text in Slack. Quite a few other apps suffer from the same limitations.
The absolute worst, however, is Google Docs. No matter what Web browser I use, it insists on capitalizing words I say after a brief pause, presumably thinking I mean to start a new sentence. Plus, it often stops putting in spaces between words for no apparent reason. Google Docs actually has its own internal Voice Typing mode, but in my quick testing, it’s horrible. It also capitalizes words willy-nilly, and worse, I have to keep clicking the microphone button or pressing its keyboard shortcut to activate it—there’s no way to keep it on while in a document.
Finally, the other problem with Voice Control is that it’s always listening. If Tonya comes into the room and starts talking to me, it picks up her voice, and if I don’t realize it in time and stop Voice Control from listening, it picks up my responses too. We end up with entire conversations in my documents, which makes for surreal reading and extra editing later. Similarly, if I need to do something on the iPhone and use dictation there, it also puts the same words in whatever document is open on the Mac. Voice Control has functional “Stop Listening” and “Start Listening” commands, but I haven’t internalized them yet. I have some ideas for how to solve this problem that I’ll share more about later.
In the meantime, TidBITS may not be quite its usual self for a while until I’m feeling better. I hope things will be back to normal soon, although research suggests I’ll be in the cast for at least 6 weeks.
ADAM ENGST 21 September 2026
Notes on Setting Up a New iPhone 18 Pro and Apple Watch Series 12
In the ongoing saga of my recovery from last weekend’s cycling accident, I’ve had a few bad mornings where I don’t want to get out of bed. Tonya and I had planned to spend Saturday at Chimney Bluffs State Park and stay overnight with friends in Rochester before driving on to Buffalo to run a cross-country race with our Finger Lakes Runners Club teams on Sunday. But when 9:30 AM rolled around and I was still in bed, feeling exhausted and dizzy, we pulled the plug on Saturday (BPPV maneuvers helped with the vertigo later in the day, happily), and Tonya planned to carpool up to the race with the rest of our runners on Sunday.
The only silver lining in this adjustment to our weekend was that FedEx had proved incapable of delivering my iPhone 18 Pro on Friday as promised. The Apple Watch Series 12 had appeared on Friday, but there didn’t seem to be much point in trying to set it up with the iPhone 17 before leaving for the weekend.
So by Saturday mid-afternoon, when I felt better, I had a new iPhone and Apple Watch to activate. I wasn’t planning to write an article then, so I didn’t take careful notes, but after I got everything set up, I ran into enough interesting quirks that I felt they were worth sharing to alert others before they experience the same things.
Pairing a New Watch and New iPhone
The first question was the order in which I should activate these devices. I could connect the new Apple Watch Series 12 to my old iPhone 17, replacing my old Apple Watch Series 9, so that when I switched to the iPhone 18 Pro, the Series 12 would come along for the ride, since it would be included in the iPhone 18 Pro’s backup. I think that would have worked, but I ended up choosing a different path.
First, I unpaired my Series 9 from the iPhone 17, which triggered a backup. Then, I activated my iPhone 18 Pro and used the iPhone 17’s iCloud backup to restore it. Once I set up the iPhone 18 Pro, I paired the Series 12 with it and used the Series 9 backup to restore it. That worked flawlessly.
I have a vague feeling that the approach I chose—unpairing the old watch first, then setting up the new iPhone, and finally pairing the new watch—was more efficient and potentially less error-prone, but I have no definitive proof.
Transferring the eSIM
Since we recently switched from T-Mobile to US Mobile to cut costs, I was curious how my number would be transferred from the old iPhone 17 to the new iPhone 18 Pro. With major carriers, you specify that you want it to happen when you buy the iPhone, and it transfers during setup.
However, US Mobile was never mentioned during the purchase process, and when it came time to transfer the phone number, I was given a somewhat confusing choice: transfer from T-Mobile—my previous account, which was disabled but still associated with an eSIM in the iPhone 17—or scan a QR code.
It turned out to be extremely easy. I went to the US Mobile website, told it I was getting a new device, and it provided a QR code to scan during setup. Although the process wasn’t nearly as automatic as with a major carrier, it was easy enough. This is the sort of minor friction that’s worth $1000 in first-year savings for our three lines.
Choosing a Restoration Method
When setting up a new iPhone, you have several ways to transfer data from your old iPhone to the new one. Apple’s Quick Start gives you two choices, and there is a third option if your old iPhone isn’t available or Quick Start doesn’t work.
For Quick Start, put your old iPhone next to the new one, follow the on-screen instructions, and use it to scan the animation that appears on the new iPhone. When Quick Start asks how you want to transfer your data, you have two choices: iCloud or a direct transfer.
Download from iCloud: Apple’s top choice is for you to restore from your old iPhone’s iCloud backup. This approach lets you start using the new iPhone while apps and data download in the background–Apple says it will take about 15 minutes before you can start using the phone. After you connect the new iPhone to Wi-Fi (which should happen automatically) and choose Download from iCloud, the process triggers another iCloud backup, even if you just made one. You want to restore from the latest backup, of course.
Transfer from iPhone: The second option is to transfer your apps, data, and settings directly from the old iPhone, either wirelessly or with a wired connection—a wired connection can help if wireless migration proves unreliable, but there’s no way to know which will be faster. With a direct transfer, whether wired or wireless, both iPhones remain unavailable until the process finishes, which could take an hour or more. For wireless transfers, keep the phones close together and plugged in.
Finder or iTunes: If you don’t have access to the old iPhone, or if Quick Start fails, you can set up the new iPhone manually, and then restore your old iPhone’s data from a backup saved to your Mac. Apple doesn’t even mention this approach in the interface, and I would use it as a last resort. When you get to the Transfer Apps & Data screen on the new iPhone, tap From Mac or PC, connect the new iPhone to your Mac, open a Finder window (or iTunes on macOS 10.14 Mojave or earlier), select the iPhone, click Restore Backup, and choose the appropriate backup.
Some years ago, I saw advice suggesting that transferring directly from the old iPhone would retain more app logins than restoring from iCloud, but in the last few years, I’ve had to re-authenticate to so many apps that I don’t think there’s much, if any, difference in this respect. Since I’m already backing up to iCloud and Apple positions iCloud restoration as the first choice, I went with that approach this time, and it worked well. It claimed it had 13.5 GB of apps and data to download, but it crunched through that fairly quickly while I did other things.
Google Account Update Chaos
For the most part, the post-update tasks went as I expected. One thing that did not was logging back into my Google account. I use Gmail, Google Contacts, and Google Calendar, and my Gmail account is set up separately in Settings > Apps > Mail > Mail Accounts so outgoing email uses my proper @tidbits.com return address rather than the underlying Gmail address. Plus, I have at least four email apps on my iPhone: Mail, Gmail, Mimestream (see “Why I Use Mimestream for Gmail,” 24 May 2023), and Avec (see “Taming Email Overload: Avec Makes iPhone Email Triage Almost Fun,” 16 July 2026).
I don’t know if any of those details are related, but after the iPhone 18 Pro finished restoring, it desperately wanted me to log in to my Google Account again. That’s not unreasonable, but I got multiple prompts to do so, interspersed with other prompts from other apps. I could only do one thing at a time, so by the time I got to logging into my Google Account again, I had already received at least four or five update requests. I assumed logging in once would satisfy all the requests, but that didn’t seem to be true, and I went through the process three or four times before I decided it was a waste of time and stopped.
In the end, I can’t really explain why this happened or whether it was actually necessary to log into my Google Account more than once, but if you use Gmail and other Google services, beware that you may get caught up in this flurry of prompts after setting up a new iPhone. My suspicion is that you can log in once and then cancel the rest, so try that if you find yourself in a similar situation. In the worst case, you’ll have to log in multiple times later.
Apple Pay Card Verification Rigmarole
The most annoying part of activating my new iPhone 18 Pro and Apple Watch Series 12 was setting up Apple Pay. Like many people, I have quite a few credit and debit cards in Apple Pay, and while the cards themselves transfer over, you have to verify ownership in multiple ways. There’s no rhyme or reason for which method a particular card uses, and some cards offer multiple choices. Worse, you may have to verify each card separately for both the iPhone and the Apple Watch. Be ready to:
Enter the CVV number: Entering the three-digit CVV number seems to be the first step for verifying all payment cards, presumably because it helps prove that you have physical possession of the card. I recommend having all the cards in front of you when you start this process.
Enter a code sent via SMS: Several of my cards could be verified by entering a code I received via text message, and at least one verified itself after receiving a text message without me having to enter a code at all.
Enter a code sent via email: Other cards wanted to send codes via email, but for one, I never received them (and yes, I checked my spam folder). Unfortunately, by the time I realized they were going to Tonya’s account, I had used up the system’s patience and had to call someone to get the card verified.
Verify with a phone call, like an animal: My most-used card forced me to fall back on an actual phone call to an actual person, so I had the pleasure of waiting on hold for 15 minutes before I could activate this card. At least iOS’s automatic Hold Assist meant I didn’t have to listen to the Muzak and constant interruptions while on hold. And the customer service person was nice.
Verify in an app: We have a Capital One Visa card for the business and a personal Discover card. Since Capital One recently purchased Discover, I was able to activate both of them by running through a process in the Capital One app on the iPhone.
Apple could do more work here to standardize and improve the user experience.
Small iOS 27 Update
The iPhone 18 Pro shipped with iOS 27.0, of course, but it also prompted me to install an update during setup. I chose to delay the installation because I wasn’t sure how Software Update was configured regarding beta installs.
Interestingly, when I went back to Software Update after everything else was done, it offered iOS 27 again. I had been set to download public betas of iOS 27, but when I turned that off, Software Update still offered iOS 27.0, but this time, it was an unusual 892 MB download that promised only bug fixes. Whatever. I installed it and haven’t noticed any changes.
Time for a New iPhone Case
Because I am moving from an iPhone 17 to an iPhone 18 Pro, which has the camera plateau that debuted in the iPhone 17 Pro last year, I cannot reuse my Smartish Gripmunk case like I could when moving from the iPhone 16 Pro to the iPhone 17. I have ordered another GripMunk case with a custom photo, but let me know if you have another iPhone case that you think is particularly impressive and worth trying.
I know that some people are fine with case-less iPhones, and the iPhone 18 Pro is noticeably heavy even without a case, but its metal sides are just too slippery, and that’s doubly problematic now that my injured hands cannot grip tightly. The main level of our house has tile floors, and I am certain that dropping the iPhone onto the tile would destroy it–the tile has broken everything else that has fallen on it, including a large Wüsthof chef’s knife, without so much as suffering a scratch.
Apple One Offer
When writing about the recent Apple TV price hikes (see “Apple TV Subscriptions Jump from $12.99 to $14.99 Per Month,” 1 September 2026), I said I was waiting to see whether Apple would give me some free months when I bought my new iPhone. I have already taken advantage of at least one of these offers in the past, so I wasn’t actually expecting it, but indeed, in the iOS Settings app, there was an offer for 3 free months of Apple One. I’ve been a little too busy to take advantage of it, so perhaps there’s another gotcha, but if you are thinking about resubscribing to Apple TV for a little while, buying an iPhone may be a way to get a few free months.
GLENN FLEISHMAN 16 September 2026
Two iPhones? In This Economy? Explaining iPhone Handoff
I’m not a fancy person with a day iPhone and a night iPhone—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.
eSIM is the virtual replacement for the increasingly tiny SIM (Subscriber Identification Module) cards that connect your phone, the network, and billing information. Some carriers already allow eSIM sharing across devices, so a phone, tablet, laptop, and smartwatch can use the same number, but that’s handled at the network level. This is the first time Apple has implemented eSIM sharing on the operating system side.
You might think that Apple already lets you share a phone number with Calls on Other Devices and Wi-Fi Calling. It’s true! But, in both cases, you’re drafting off your iPhone. Here’s how iPhone Handoff is distinct from those two features:
Using Calls on Other Devices (Settings > Apps > Phone > Calls on Other Devices) requires your iPhone to be within Bluetooth range of the iPad or Mac you’re calling from, since your device uses the iPhone to place the call. And it doesn’t work from one iPhone to another.
Wi-Fi Calling doesn’t require proximity between devices, because your device uses Wi-Fi to connect to your carrier’s network to place the phone call (Settings > Apps > Phone > Wi-Fi Calling). However, it only works when your device has access to a Wi-Fi network.
The new iPhone Handoff clones your eSIM to another iPhone. Both iPhones can place calls over a cellular network as if they were the same iPhone, although only one can be active at a time. No Wi-Fi is required, and the other iPhone doesn’t need to be nearby.
If you’re interested in iPhone Handoff, you may have to wait for your carrier to support it, or even switch carriers. Only T-Mobile in the US and Deutsche Telekom in Germany currently offer the service. T-Mobile charges $5 per month to use it. Deutsche Telekom offers iPhone Handoff as part of its MultiSIM service, which connects up to eight devices; some of its plans include MultiSIM at no extra charge, while others charge an extra €6.95 per month for MultiSIM.
To set up iPhone Handoff, both iPhones must have iOS 27 installed, share the same Apple Account login, and have Messages in iCloud activated to ensure Messages sync. You must also be signed into Messages and FaceTime with the same Apple Account, which is typical for most people, but might be a problem if you use each iPhone for a personal/work split. (Messages in iCloud has a very slight security risk if you don’t also enable Advanced Data Protection in iCloud. I cover this in greater depth in my book Take Control of Securing Your Apple Devices.)
Once you’ve enabled iPhone Handoff on your calling plan, you can use Settings > Cellular > iPhone Handoff on the iPhone with the eSIM installed to copy the eSIM over and turn the service on. Hold the two phones close together, and iOS prompts you to choose one as the “primary” and the other as the “secondary.” Apple describes slightly more complicated steps if you’re setting up a new iPhone from scratch, among other scenarios.
Picking which phone to make the primary involves some strategizing due to Apple’s limitations:
Some services, like Call Forwarding and Caller ID, may work only with the primary phone, Apple says.
You should pair your Apple Watch with the device you’ll use most, which may not be the iPhone it’s currently paired with. If the paired iPhone isn’t near your Apple Watch when you’re using the other iPhone, you may have some issues with syncing and data access.
Although you can add payment cards and car keys to Wallet on both devices, transit passes, IDs, and corporate badges may only work on one device at a time.
In use, iPhone Handoff relies on which iPhone you unlock. If you unlock the one that’s currently active, nothing happens. However, if you unlock the other iPhone, that activates iPhone Handoff, and it shows “Switched to this iPhone.” If you unlock both at the same time, I imagine bad things happen—will the entire cellular network crash, and will it be your fault? Apple doesn’t explain what would happen. I expect you’d get errors on both phones. The feature isn’t designed to let two iPhones make calls at the same time, but to let you use one number across two iPhones.
Calls, voicemail, and messages (SMS/MMS, RCS, and iMessage) all appear first on the active phone, which is also used as your current location for Find My. Presumably, when you switch to the secondary phone, all the communications that arrived on the primary one will sync over quickly, and vice versa.
So who is this feature for? I’ve had a hard time coming up with use cases beyond it being a godsend for iPhone reviewers, of course, who need to test new phones in real-world situations—that’s much easier when the test phone can be used for everything alongside the reviewer’s everyday phone. Perhaps this is in anticipation of people keeping an older, but useful iPhone when they buy an iPhone Duo? I can see that, given the Duo’s size and weight. I’ve sometimes had an older and newer iPhone, and I would have enjoyed this feature if I did more rugged activities (biking, kayaking, rock climbing, skydiving), where I’d prefer to put an older iPhone at risk.
Or there’s a weirdly underserved market of people who have personal and work phones, but want to use the same number on both, and have their Messages and FaceTime synced? But it’s hard to imagine it being useful for most of those people, who presumably want different phone numbers, message storage, and apps.
I have to assume Apple received enough requests for this feature, including from internal executives and staff, to feel it was worth developing. Or carriers found enough customers wanted to share a single number across multiple devices—like Deutsche Telekom’s more involved MultiSIM offering—that they convinced Apple to add iPhone Handoff. Is it something you’ll want to use in iOS 27?
For me, I have one iPhone, one iPad mini, one MacBook Pro, and one Mac Studio. I think I’m set!
For more about iPhone and Apple communications apps and options, Glenn Fleishman wrote an entire book, Take Control of FaceTime and Messages(which includes the Phone app). He is currently updating it for 27. If you buy the book now, you’ll get the upcoming edition for free.
Watchlist
AGEN SCHMITZ 21 September 2026
Carbon Copy Cloner 7.2
Bombich Software has issued Carbon Copy Cloner 7.2 with scheduling setting updates for the drive cloning and backup utility. The release adjusts the “When files are modified on the source” scheduling setting to let the destination volume remain unmounted while monitoring the source, and adds support for network volume destinations. The new version also revises Bootable Backup tasks to perform incremental updates to the destination (as long as the macOS version remains the same on both locations), modernizes the user interface in the Settings window, improves handling of files that can’t be opened when the screen is locked, makes adjustments to the collection of snapshots when a volume is selected in CCC’s sidebar, addresses a Golden Gate-specific issue with making bootable copies of volumes that contain an older OS than the current startup disk, and removes TouchBar support. ($49.99 new, free update, 30.1 MB, release notes, macOS 13+)
AGEN SCHMITZ 21 September 2026
ChronoSync 12.0.3
Econ Technologies has issued ChronoSync 12.0.3, enhancing the cloud-managed folder readiness check to better distinguish between iCloud and File Provider Extension-managed folders. The synchronization and backup tool also updates the way Spotlight indexing is suspended on a volume before unmounting it to prevent a full re-index when the volume is re-mounted, no longer allows storing Sync Task documents in a cloud-managed folder, fixes a bug in the cloud-managed folder readiness check that would fail to suggest switching to an iCloud or File Provider Extension connection type, resolves a crash that occurred when trying to retrieve or set a Finder/Spotlight comment in macOS 27 Golden Gate, and addresses a problem with identifying bootable volumes in Golden Gate. ($49.99 new with a 20% discount for TidBITS members, free update, 102.7 MB, release notes, macOS 10.14+)
AGEN SCHMITZ 21 September 2026
Evernote 11.34.8
Evernote has released version 11.34.8 of its information management app with a refreshed PDF editor that adds a new page sidebar, lets you merge and split PDFs, and improves text formatting. The update also enables you to create toggle lists from the formatting toolbar, view transcription for older files, and adds support for AI title suggestions on notes that contain only attachments. The AI Assistant can now interact with your comments and show the context it’s working with at the top of the chat. The release also resolves an issue where search or navigation could unexpectedly return you to All Notes or show stale results, fixes AI Assistant edits not appearing correctly in notes with Tasks blocks, and improves calendar notification setup and controls so they better reflect your calendar connection and permissions. (Free/$99/$249 new from Evernote or the Mac App Store, free update, 348.2 MB, release notes, macOS 11+)
AGEN SCHMITZ 21 September 2026
Fantastical 4.2 and Cardhop 2.5
Flexibits has released Fantastical 4.2 and Cardhop 2.5. Fantastical adds support for Siri AI to work with Fantastical calendars, adds the ability to set invitee options on Microsoft Graph events, enables you to to ignore an invite notification for all events in a series, improves search to handle different punctuation variants, improves email ingest by adding support for tasks, enhances MCP results so mirrored events are no longer included, fixes a bug where search results would be slow to appear when performing multiple searches back to back, addresses a problem with the text field not updating immediately when setting a reminder location, and fixes a bug where changing the recurrence rule of a task would also change its due date.
Cardhop adds support for extra-large and extra-large portrait sizes for the Quick Action and Celebrations widgets and resolves an issue with the country field clipping when editing certain addresses. ($56.99 annual subscription includes both from Flexibits and the Mac App Store, free updates, 60/25 MB, Fantastical release notes/Cardhop release notes, macOS 12+)
AGEN SCHMITZ 21 September 2026
OmniFocus 4.9
The Omni Group has updated its OmniFocus task management app to version 4.9 to add compatibility with macOS 27 Golden Gate and support for date-parsing assistance via Apple Intelligence. The release can optionally consult the on-device Apple Intelligence model when the built-in date parser can’t resolve an entered date for improved natural language input (a beta feature that requires an Apple Intelligence-enabled device). It also adds support for Siri AI reminder functionality in Golden Gate, which enables Siri to know about reminders in OmniFocus, as well as lists and groups that can contain reminders. Additionally, OmniFocus 4.9 adds several new Shortcuts actions, allows interactive status circles to be turned off in Widgets, replaces Linked Folder functionality with Connected Folders, updates the appearance of the Forecast sidebar calendar to match Liquid Glass design elements better, ensures custom notifications are correctly titled, displays the Perspectives Bar as a sidebar in Golden Gate, and now requires a minimum of macOS 15.2 Sequoia. ($74.99 new for Standard, $149.99 for Pro, or $9.99 monthly subscription, 41.4 MB, release notes, macOS 15.2+)
AGEN SCHMITZ 21 September 2026
OmniOutliner Essentials and Pro 6.3
The Omni Group has released version 6.3 of OmniOutliner Essentials and OmniOutliner Pro to provide compatibility with macOS 27 Golden Gate. The outlining and information organization apps also improve the reliability of the Omni Automation Plug-In action, fine-tune Liquid Glass design elements throughout the application, update the user interface to place the outline behind the Inspector to give a consistent look to the sidebars, allow the Edit Link popover to be dismissed, add an API that looks up available APIs by searching the Omni Automation API documentation, and fix a crash on launch when the Color Picker is being restored. ($24.99 new for Essentials, $99.99 for Pro, available from the Mac App Store, free updates, 59.1 MB, release notes, macOS 15+)
AGEN SCHMITZ 21 September 2026
PowerPhotos 3.4.7
Fat Cat Software has released PowerPhotos 3.4.7 with support for star ratings in AppleScript and Shortcuts in macOS 27 Golden Gate. The Photos library manager also enables you to include star ratings when exporting in Golden Gate, fixes a bug where the “Don’t Delete Any” option would still attempt a deletion, resolves an issue where other photos could be removed from an album when copying/moving photos, addresses an error that could appear when choosing Check for Updates after an update had already been downloaded in the background, and fixes a bug that caused a failure to create a new library. ($39.95 new, free update, 41.4 MB, release notes, macOS 14+)
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