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If Mail Fails to Send, Try, Try Again (Instead of Changing Servers)

Sometimes, something goes wrong, causing Mail on the Mac to have trouble sending a message. When it does, you may see an error like the one below, encouraging you with a default button to try another configured server. Don’t do it! Always click Try Later. If that still doesn’t work, contact your favorite tech support professional to troubleshoot the problem with the SMTP server associated with the account from which you’re sending. Attempting to send through another SMTP server is a recipe for trouble because various anti-spam checks may fail, causing your message to be filtered as spam or bounced back to you. Worse, if you select a different server and click Try With Selected Server, Mail remembers that choice going forward, so you will have to reset it manually later.

(Featured image by iStock.com/Marut Khobtakhob)


Social Media: If Mail on your Mac throws an error about being unable to send a message, always have it try again later rather than switching to a different server. Otherwise, your messages may look like spam and be blocked.

Use This Hidden Setting to Stop Triggering Caps Lock Accidentally

There’s little more annoying than accidentally touching the Caps Lock key while typing and having your text suddenly TURN INTO CAPITAL LETTERS, which we all know is seen as shouting. Unless you have some reason to type in capital letters regularly, you can prevent this mistake by disabling the Caps Lock key or remapping it to another modifier key. In macOS 13 Ventura and later, choose System Settings > Keyboard > Keyboard Shortcuts > Modifier Keys, and choose from the pop-up menu next to Caps Lock. (In earlier versions of macOS, open System Preferences > Keyboard > Modifier Keys.)

(Featured image by Adam Engst)


Social Media: If you very seldom want to type in all caps, disable or remap the Caps Lock key so an errant key press doesn’t turn it on accidentally.

Feel Free to Upgrade to macOS 14 Sonoma When You’re Ready

Although we’re cautious about recommending that people upgrade to the latest major release of macOS, we think Apple has done a good enough job with macOS 14 Sonoma that anyone who wants to upgrade can do so now. That doesn’t mean you have to upgrade immediately, but there’s no major reason most people need to delay.

Our confidence comes from our positive experience working with those who have upgraded to Sonoma and the fact that Sonoma has received only three updates so far.  None included significant bug fixes:

  • macOS 14.1 fixed two bugs that could reset the System Services settings within Location Services and prevent encrypted external drives from mounting.
  • macOS 14.1.1 came with generic release notes, but the community discovered that it fixed a bug introduced in 14.1 that affected Photoshop and another that could prevent a new M3 24-inch iMac that shipped with macOS 13 Ventura from upgrading to Sonoma.
  • macOS 14.1.2 focused on fixing two WebKit-related security vulnerabilities that were exploited in iOS.

Apple will likely release another update before the end of the year, probably macOS 14.2, with some promised features, a few more bug fixes, and the usual handful of security improvements. After that, the company will continue with an update every month or so to address newly discovered bugs and security vulnerabilities.

That said, you can put off the Sonoma upgrade as long as you’re running macOS 12 Monterey or macOS 13 Ventura and are staying current with Apple’s security updates. Earlier macOS versions no longer receive security fixes, rendering them more vulnerable to attack. Possible reasons to continue delaying include:

  • You’re too busy. The upgrade process will take a few hours, plus some additional time to configure everything properly afterward. When you are ready to upgrade, aim for when a little downtime will be convenient.
  • You rely on incompatible software. The jump from Monterey or Ventura to Sonoma isn’t a big one, so most modern apps should have been updated by now. But if you’re still running macOS 10.14 Mojave or earlier with 32-bit apps, you’ll lose access to them if you upgrade. There’s nothing new here—32-bit apps stopped working in macOS 10.15 Catalina in 2019. Rather than delaying, consider running Mojave and your 32-bit apps in a virtual machine using VMware Fusion or Parallels Desktop.
  • You need consistent versions for workflow reasons. We’re unaware of any examples here, but it’s conceivable that a coworker could be stuck on an older version of macOS and older versions of shared productivity apps. If your upgrade would force you to update those apps and introduce compatibility issues when collaborating with that coworker, you may have to wait until your coworker can upgrade as well.

Sonoma won’t transform your experience of using a Mac, but it has new features you might appreciate. The most noticeable is probably desktop widgets that provide updated information at a glance—you can even add widgets from your iPhone. Sonoma also lets you turn websites in Safari into standalone apps, enjoy aerial screensavers from the Apple TV, create a video overlay of yourself on video calls when sharing your screen, autofill PDF forms, and use the keyboard while dictating.

Before You Upgrade

Once you’ve decided to upgrade to Sonoma, you have three main tasks:

  • Update apps: Make sure all your apps are as up-to-date as possible. If you regularly put off updates, now’s the time to let them complete so you have Sonoma-compatible versions.
  • Clear space: Sonoma may need as much as 25 GB of free space to upgrade, and the Sonoma installer itself is about 12 GB, so we recommend making sure you have at least 37 GB free. Don’t cut this close—you should always have at least 10–20% free space for virtual memory, cache files, and breathing room. Check in Ventura by choosing System Settings > General > Storage; in earlier versions of macOS, choose About This Mac from the Apple menu and click Storage. System Settings provides quick ways to free up space. Another easy one for iCloud Drive users is to Control-click large folders and choose Remove Download to “evict” the local versions of those files temporarily; Box, Dropbox, and Google Drive have similar features.
  • Make a backup: Never, ever install an update to macOS without ensuring you have at least one current backup first. In an ideal world, you’d have an updated Time Machine backup, a duplicate, and an Internet backup. That way, if something goes wrong, you can quickly revert.

Upgrading

After completing those tasks, ensure you won’t need your Mac for a few hours. There’s no telling exactly how long the upgrade will take, so never start an upgrade if you need the Mac soon.

Initiating the upgrade is just a matter of opening System Settings > General > Software Update in Ventura (System Preferences > Software Update in previous versions of macOS), clicking the Upgrade Now button, and following the instructions. If you’d like more handholding, check out Joe Kissell’s ebook Take Control of Sonoma.

After You Upgrade

Part of the reason to set aside plenty of time for your Sonoma upgrade is that there are usually cleanup tasks afterward. We can’t predict precisely what you’ll run into, depending on what version of macOS you’re running now and what apps you use, but here are a few situations we’ve noticed in the past:

  • macOS may need to update its authentication situation by asking for your Apple ID password, your Mac’s password, and if you have another Mac, its password as well. Don’t worry that your Mac has been compromised by malware—it’s fine.
  • Some apps may have to ask for various permissions even though you previously granted them. Again, that’s fine and won’t happen again.
  • If you use your Apple Watch to unlock your Mac and apps (and you should, it’s great!), you may need to re-enable that in System Settings > Touch ID & Password (or Login Password on a non-Touch ID-enabled Mac (previously, it was in System Preferences > Security & Privacy > General).
  • If you use Gmail, Google Calendar, or other Google services, you may need to log in to your Google account again.
  • Websites that usually remember your login state may require that you log in again. If you’re using a password manager like 1Password, that’s easy.
  • You may have to re-enable text message forwarding to your Mac. You do this on your iPhone in Settings > Messages > Text Message Forwarding.

With all that housekeeping done, it’s time to check out all the new features in Sonoma!

(Featured image by Apple)


Social Media: When should you upgrade to macOS 14 Sonoma? There’s no need to install it today, but we think it’s now safe for those who want to take advantage of the new features and integration with Apple’s other operating systems.

Open the Mac’s Control Center with This Obscure Keyboard Shortcut

With macOS 13 Ventura, Apple brought Control Center from iOS to the Mac, providing a unified interface for features that users need to turn on and off regularly or that receive frequent adjustments, like screen brightness and audio volume. Clicking the Control Center icon in the menu bar brings it up, but it’s a small, hard-to-hit target. For faster and easier access to Control Center from within any app, press fn-C. (All current Apple keyboards have an fn key, but if you’re using a third-party keyboard that lacks one, you’re out of luck.)

(Featured image by Adam Engst)


Social Media: Control Center brings together controls for a collection of core macOS features, but its menu bar icon is small, making it hard for some to click. Luckily, there’s a hidden shortcut to bring it up quickly from the keyboard.

In Your Face App Guarantees That You Notice Appointment Alerts

It’s easy to get caught up in what you’re doing and miss an alert for a Zoom meeting or a reminder to leave for an appointment. The Mac app In Your Face ensures that will never happen again by taking over the entire screen for notifications and requiring that you click a button to dismiss or snooze it. It can also play sounds repeatedly, lets you pick which calendars and reminder lists to use, gives you single-click access to videoconference links in events, and shows ongoing and upcoming events in the menu bar. In Your Face costs $1.99 per month or $19.99 per year, or it’s available in the $9.99 per month Setapp bundle of over 230 Mac apps.

(Featured image by Blue Banana Software)


Social Media: Are you often late to online meetings or in-person appointments because you were too focused on your work to notice the time? The In Your Face app ensures you’ll never miss an important meeting again.

Is Your Mac Running Low on Disk Space? Here’s How to Delete Unnecessary Files

Between apps, photos, videos, music, and downloads, it’s easy to fill up your Mac’s drive, particularly one with just 128 or 256 GB of drive space. macOS warns you when you get too low on space, but those warnings may come late—for optimum Mac performance, we recommend you keep at least 10–20% of your drive free for new downloads and virtual memory swap files. There are excellent utilities that help you find and delete unnecessary files, such as the free GrandPerspective, the $9.99 DaisyDisk, and the $14.99 WhatSize, but Apple’s built-in storage management capabilities will likely be all you need.

Apple first introduced its Storage Management tool in the System Information app in macOS 10.12 Sierra, making it accessible from the About This Mac dialog. Starting in macOS 13 Ventura, Apple moved those capabilities to System Settings > General > Storage, providing a quick overview of your drive usage at the top. Hover over each colored bar to see how much space is taken up by a particular type of data. The light gray space at the end of the bar is what’s still available.

Below the graph, macOS may offer some recommendations for reducing storage over time, but they come with tradeoffs. Storing files in iCloud and optimizing Apple TV videos will replace local files with stubs pointing at a version stored in the cloud. That’s OK, but you then have to download the original before you can use it. Deleting files automatically after they’ve been in the Trash for more than 30 days is also fine but could have undesirable results if you ever want to recover older files from the Trash. Enable these if you wish, but the real work happens farther down on the screen, where you find all the categories of files you can explore. Depending on what apps you use, they will vary a bit between Macs, but they correspond to the colored bars you saw in the storage graph. Double-click each one to see what it displays.

For a few app-specific categories, like Mail and Podcasts, you merely learn how much space the app’s data occupies—to save space, you must delete unnecessary data from within the app itself. iCloud Drive and Photos are similar but also let you enable space optimization, which stores only placeholder files or smaller optimized photos on the Mac, leaving the originals in iCloud for later downloading whenever you access them.

More interesting are the Applications, Documents, and iOS Files categories, each of which may reveal gigabytes of unnecessary data. iOS Files, for instance, shows any device backups and software updates stored on your Mac’s drive. It’s worth keeping the latest backup of devices you still use, but delete any older backups and updates that are just wasting space—well over 8 GB in the screenshot below.

The Applications category lists your apps and is sorted by size by default. But try clicking the column header for Kind and scrolling down. You can probably delete most apps tagged as Unsupported, Duplicates, or Older Versions. Similarly, click the Last Accessed column header to see which apps you haven’t launched in years. Many of them can probably go, too.

In Documents, you’ll see four buttons: Large Files, Downloads, Unsupported Apps, and File Browser.

  • Large Files shows huge files regardless of where on your drive they’re located.
  • Downloads shows you the contents of your Downloads folder, much of which you likely don’t need.
  • Unsupported Apps lists any PowerPC or 32-bit apps that won’t run on your Mac. You can delete them.
  • File Browser provides a column view sorted by file size and shows sizes next to each item. It’s great for trawling through your drive to see what’s consuming all that space.

In any of these views, click Delete or Move to Trash to remove the file or Show In Finder to see it in its native habitat, which may help you decide if you should keep or delete the file. To delete multiple files at once, Command-click or Shift-click to select them and then click Delete to remove them all at once.

You may find it worth using GrandPerspective to get a visual overview of how space is used on your drive. After scanning, which can take a long time, it uses tiny colored blocks to represent files, collecting multiple blocks into bigger rectangles to show folder size. Toolbar buttons let you open, preview with Quick Look, reveal location, or delete whatever file block you click. Look in the status bar at the bottom of the window to see the path to the file.

In the screenshot below, the big boxes of color are massive virtual machine disk images, and the selected folder outlined in white at the right contains desktop pictures downloaded by an app that rotates them regularly—gigabytes of old files that can easily be deleted.

If your Mac’s drive has less than 10% free space, consider using Apple’s storage management capabilities—perhaps supplemented with GrandPerspective or another utility—to find and delete files that are wasting space.

Two final notes: Don’t get too wrapped up in the exact numbers in the storage graph matching what the Finder reports, and give the Mac some time to update its free space amounts after deleting files directly or emptying the Trash.

(Featured image based on an original by iStock.com/Bet_Noire)


Social Media: Is your Mac low on drive space? Learn how to use Apple’s built-in storage management capabilities—perhaps supplemented with a third-party utility—to find and delete gigabytes of unnecessary files.

Erase Image Content in Preview with Copied Color Blocks

Apple’s Preview is a surprisingly capable graphics editor for making quick changes to screenshots and other illustrations, but it lacks a built-in way to delete content while leaving the background. Here’s the workaround—select a rectangle of the background color, copy it, paste it, and then move it over the undesirable content—as shown in the After screenshot below, where blue selection dots denote the pasted box. As you resize the box, press Shift to prevent it from resizing proportionally, which helps you make it the shape you want. If you need a second box of the same color, Option-drag the first box to copy it. When you save and close, your boxes will be merged into the image, permanently removing the content underneath, so make sure they’re in the right spot before moving on.

(Featured image based on an original by iStock.com/Seetwo)


Social Media: Have you ever needed to remove some content from a screenshot or other illustration? There’s no need for a fancy graphics app—you can do it quickly in Preview with this little-known trick.

Frustrated by System Settings? Use the View Menu or Search

In macOS 13 Ventura, Apple replaced the creaky System Preferences with System Settings, which uses a more iOS-like interface. Many people find System Settings overwhelming, partly because they had memorized where to look in System Preferences (but System Settings has many other design flaws as well—it’s not your fault). We have two recommendations to make it more easily navigable. First, for an alphabetical approach, use the View menu, which lists the panes that way, along with the top-level items in the General settings pane. Second, make heavy use of the search field at the top of the System Settings sidebar—it’s the only way to find some deeply nested settings.

(Featured image based on an original by iStock.com/rootstocks)


Social Media: If you have trouble finding things in macOS Ventura’s System Settings app, you’re not alone. We have advice to help you navigate alphabetically or jump directly to a deeply nested setting.

Mac Keyboard Shortcuts Performing Unexpected Actions? Check These Settings

Keyboard shortcuts are a productivity win, but they can cause confusion if something unexpected happens when you inadvertently press some system-wide key combination. For instance, you might be taken aback if you accidentally press Control-Option-Command-8 and all the colors on your Mac screen suddenly invert. Although Apple has pages listing shortcuts and the KeyCue utility can list them all for any app, a good way to see—and manage—what’s active on any Mac is to open System Settings > Keyboard > Keyboard Shortcuts (look in the same place in System Preferences in macOS 12 Monterey and earlier) and scan the categories. Disable shortcuts you’ll never use by deselecting their checkboxes, and redefine others so you’ll remember them.

(Featured image by iStock.com/spaxiax)


Social Media: Do strange things sometimes happen on your Mac when you inadvertently press certain key combinations? Take a trip through the macOS keyboard shortcuts and turn off those you’ll never use intentionally.

With Storms Increasing, Protect Your Tech Gear from Damaging Power Fluctuations

It has been a tough year for extreme weather events. While the connection between weather and technology may seem tenuous, heat waves, high winds, and lightning strikes can play havoc with all sorts of powered and networked electronic devices.

Anything that causes power fluctuations—spikes, surges, sags, brownouts, and blackouts—can hurt your tech gear. Protecting your most vulnerable devices doesn’t have to be expensive, but don’t be complacent because you plug your Mac into a cheap surge protector you’ve had since college. And note that many power strips offer no surge protection at all.

First off, why are power fluctuations problematic? There are two scenarios:

  • Too little power: Sags and brownouts are drops in voltage; a sag is a short-term dip, whereas brownouts last longer. Blackouts are complete power outages. Although they’re less damaging than surges, sags and brownouts can cause electronic devices to behave erratically or crash, and the fluctuation in voltage—particularly when coming back from an outage—can stress components. Losing power entirely will cause you to lose any unsaved work and possibly end up with document or even drive corruption.
  • Too much power: Spikes and surges are sudden, brief increases in voltage; the difference is that spikes are shorter than surges. Either way, the excessive power can degrade or damage sensitive electronic components, reducing lifespan or causing immediate failures.

The best solution to these scenarios is an uninterruptible power supply (UPS). Put simply, a UPS is a big battery into which you plug your Mac and other peripherals. It then plugs into a wall outlet and monitors the incoming power. If the power surges, falls below a certain threshold, or fails outright, the UPS switches the power source to its internal battery. This happens so quickly that your Mac never even notices.

If your gear is plugged into a UPS when a blackout hits, you get some time to save your work and shut down gracefully, ensuring that you don’t lose data or flirt with drive corruption. A UPS also protects against spikes and surges, filtering out the excess voltage so it can’t harm the devices plugged into it. The downsides to UPSes are that they’re an extra expense, their batteries need replacing every few years, and they take up space under your desk. For a home or small office UPS, consult Wirecutter’s recommendations. For larger installations, contact us.

If power outages are rare in your location, you may prefer to rely on a surge protector instead of a UPS. As the name implies, surge protectors filter out voltage spikes and surges so they won’t damage your gear. Surge protectors are smaller and less expensive than UPSes, and while they don’t have batteries to fail, their protection circuitry degrades over time, so they should be replaced every few years as well. Better surge protectors alert you or stop working entirely when they can no longer provide protection. Again, Wirecutter has good recommendations.

If most of your expensive tech gear is battery-powered, you could forgo even a surge protector. Outages aren’t an issue, and a MacBook or iPhone power adapter will protect against most sags, brownouts, spikes, and surges. The power adapter may incur damage, but it’s inexpensive to replace.

One final thought. No UPS, surge protector, or power adapter can protect against a direct lightning strike. Lightning is too fast and too powerful—it’s millions or even hundreds of millions of volts. Even turning your equipment off isn’t sufficient because lightning that has traveled miles through the air to hit the ground can easily jump across an open switch. If lightning strikes are common in your area, unplug your most expensive devices entirely during severe storms.

To sum up:

  • For a desktop Mac and peripherals, a UPS is a worthwhile investment if you ever suffer from power outages. Also, consider a UPS for essential networking gear—cable modems, routers, switches, and network-attached storage.
  • If power outages are extremely rare, or for equipment that doesn’t need to remain on during an outage, get a good surge protector. If it doesn’t automatically disable itself when it’s no longer effective, write the date on the bottom and replace it in a few years.
  • Although there’s no harm in doing so, it’s not necessary to plug battery-powered device chargers into a surge protector or UPS. A spike or surge may damage them, but they’ll probably sacrifice themselves to protect your gear.
  • When in doubt during severe storms, unplug your most valuable equipment to protect against a direct lightning strike.

(Featured image by iStock.com/HardRockShotz)


Social Media: How can you protect your tech gear from unexpected power fluctuations? A UPS is best in some scenarios, but a not-too-old surge protector is often sufficient.  You can also let your Apple chargers do their job without worrying about what they are plugged into.