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

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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.

How to Turn Mail’s Rich Website Previews into Plain Links

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Sometimes apps can be too helpful. Apple’s Mail on the Mac likes to turn pasted URLs into graphically rich previews, and sometimes that’s OK. But other times, the preview is confusing or takes up too much space. Or you may want to send a plain link so the recipient can see its text. There are three ways to avoid rich link previews:

  • Before pasting a URL into your message, type a space or any other text. Mail converts URLs to rich previews only when they’re on a line by themselves.
  • Hover over the preview, click the down-pointing arrow that appears, and choose Convert to Plain Link from the pop-up menu.
  • In Mail > Settings > Composing, change the Message Format pop-up menu to Plain Text. Although this eliminates rich link previews, it also prevents you from including formatting and images.

(Featured image by Adam Engst)

Social Media: Annoyed by how Apple’s Mail on the Mac turns pasted URLs into rich link previews? We offer three ways to avoid them.

11 Features to Look Forward to in Apple’s 2022 Operating Systems

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It’s that time of year again. Apple CEO Tim Cook and numerous Apple employees took the virtual stage again at the company’s Worldwide Developer Conference keynote on June 6th to share what we can expect to see later this year in macOS 13 Ventura, iOS 16, iPadOS 16, and watchOS 9. (Almost no mention was made of tvOS or the HomePod, but Apple will undoubtedly move them forward in small ways as well.)

The announcements came thick and fast, and like last year, many of the technologies cut across several of Apple’s operating systems. Before we dive in, however, remember that some older devices won’t be able to upgrade. Here are the basic system requirements, though certain features won’t be available on all devices:

  • macOS 13 Ventura: iMac, iMac Pro, MacBook, and MacBook Pro from 2017 and later. MacBook Air and Mac mini from 2018 and later. Mac Pro from 2019 and later. Mac Studio from 2022.
  • iOS 16: Second-generation iPhone SE, iPhone 8, and later
  • iPadOS 16: Fifth-generation iPad and later, fifth-generation iPad mini and later, third-generation iPad Air and later, and all iPad Pro models
  • watchOS 9: Apple Watch Series 4 and newer, including the Apple Watch SE

Here are the promised new features we think will have the most impact on your Apple experience. Assume that these features are available on the Mac, iPhone, and iPad unless otherwise specified.

Customizable iPhone Lock Screen

We’ve been able to put a photo on the iPhone’s Lock screen for years, but that’s it. With iOS 16, Apple is opening up lots of customization options along the lines of what you can do to Apple Watch faces. To start, you can customize the font, color, and placement of various options, just like a watch face. Photos dynamically display in front of the time, and you can have a set of photos shuffle throughout the day. Widgets from Apple and third-party developers provide at-a-glance information so you can check the weather, say, without even unlocking your iPhone. Notifications now scroll up from the bottom, and Live Activities help you stay up on the music that’s currently playing or the latest score in the big game.

Messages Gains Editing, Undo Send, and Mark as Unread

At long last, Messages will let us edit messages after sending, undo sending to call a message back, and mark messages as unread. The first two features are essential for clear communication, especially when you’re fixing auto-correct failures, and being able to mark messages as unread ensures that you won’t forget to respond to something that you read when you’re not in a position to reply.

Mail Adds Undo Send, Scheduled Send, Follow-up, and Remind Me

It’s surprising that Apple hasn’t spent more time on Mail in recent years, but that’s changing in 2022, when it will gain some welcome features that are commonplace in other email apps. You’ll be able to undo sending, which is helpful when you remember something to add to a message within 10 seconds after clicking the Send button. For more specific timing, scheduled send lets you specify when a message should go out. This is helpful when you are working on the weekend or late at night but don’t want your co-workers to feel that they need to reply right away.  Mail will also move sent messages that haven’t received replies to the top of your inbox so you can follow up, and you can set a reminder to come back to messages that you’ve opened but not dealt with (many of us just mark those as unread).

Multi-Stop Routing in Maps

No longer are you limited to a single destination when creating a route in Maps. You’ll be able to specify up to 15 stops on a route, making it easy to build a trip that includes a swing by your favorite diner, a quick visit with an old friend, and a pilgrimage to the World’s Largest Bull in Iowa.

iCloud Shared Photo Library Improves Family Photo Sharing

Apple’s latest attempt to help families share photos looks like the best yet—certainly better than the shared Family album that’s created for Family Sharing groups now. It will be a completely separate iCloud photo library shared with up to five other people. You’ll be able to populate it with all your existing photos or a subset based on start date or who’s in them. Everyone will have equal permission to add, edit, favorite, caption, and delete photos, so maintaining and improving it becomes a group activity. Sharing new photos will be easy with a switch in the Camera app, automatic sharing based on proximity to family members, and sharing suggestions in Photos.

Passkeys Aims to Replace Passwords… Eventually

Apple’s new Passkeys technology, which is associated with the work of an industry consortium called the FIDO Alliance to ensure cross-platform support, aims to replace passwords for websites and apps with private passkeys that are stored only on your device and accessed by Touch ID or Face ID. Passkeys are easier to use than passwords and significantly safer because they can’t be stolen from websites and each one is specific to the site for which you create it. They’ll be available on all your Apple devices, syncing end-to-end encrypted through iCloud Keychain.

Use Your iPhone as a Webcam for Your Mac

Mac webcams are nowhere near as good as the rear-facing cameras in your iPhone, so Apple is helping us improve our videoconferencing by using an iPhone as a webcam and microphone. The feature, called Continuity Camera, works wired or wirelessly and can automatically switch to using your iPhone as a webcam when you bring it close to your Mac. It provides Portrait mode to blur the background, Center Stage so you can move around, Studio Light to dim the background and illuminate your face, and even Desk View to show what’s on your desk in front of your Mac. Apple says Belkin will be making clips to attach your iPhone to your Mac.

Stage Manager Offers New Window Management Approach

We’re not yet sure what to make of Stage Manager, which is Apple’s new approach to window management on the iPad and Mac. It puts one app in the center of the screen while keeping other apps off to the side, making it easy to flip between apps or show multiple apps at once. It doesn’t replace traditional window management—you have to turn it on in Control Center—so you won’t be forced to change, but it might be welcome, especially on the iPad, where it also enables the use of an external display.

Simultaneous Dictation, Touch Selection, and Keyboard Editing

On the iPhone and iPad, you’ve been able to tap a microphone button to invoke Dictation, a huge boon when you want to send a message without typing. In iOS 16 and iPadOS 16, Apple has radically improved Dictation, so you can now simultaneously talk, type, edit on the keyboard, select text via touch, and use the Apple Pencil (on an iPad). Dictation will also automatically add commas, periods, and question marks as you dictate, and you can insert emojis with voice commands. Sadly, it seems that the Mac gets only the punctuation and emoji capabilities.

Medications App on the Apple Watch

Many of us have to take medications, vitamins, and supplements regularly. To help us better manage our health, Apple is adding the Medications app to watchOS 9. You’ll be able to enter your meds in the Health app on the iPhone, be alerted to any critical interactions between drugs, and have your Apple Watch notify you to take the right pills at the right times.

Weather App Appears on the iPad and Mac

Finally, because our list goes to 11, Apple says it’s bringing the Weather app to the iPad and the Mac. Since Weather has been on the iPhone since the beginning, it’s hard to fathom what took Apple so long. If you haven’t already jumped ship for one of the 17,000 other weather apps out there, you’ll be able to enjoy using Apple’s built-in app in iPadOS 16 and macOS 13 Ventura.

Apple’s upcoming operating system releases boast many other new features, and we plan to explore more of them once everything ships in a few months. We’ll let you know when it’s time to update!

(Featured image by Apple)

Social Media: At its Worldwide Developer Conference keynote, Apple announced oodles of new features that we’ll see in macOS 13 Ventura, iOS 16, iPadOS 16, and watchOS 9 later this year. Here are the ten—no, eleven!—features we think you’ll most like:

Losing the Occasional Important Message? Set up a Ham Filter

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Although spam remains as much of a scourge as ever, spam filters have improved enough that most people see relatively little spam and lose relatively few legitimate messages (known as “ham”) to spam filters. However, good email messages are still sometimes caught by spam filters. To reduce the chance of missing an important message, consider making a “ham filter.” A ham filter looks for certain words—usually proper nouns—that are likely to appear only in legitimate messages and then marks such messages as Not Spam or moves them out of a Spam folder. (This capability is available in Gmail and can be emulated with multiple rules that you create in Apple’s Mail preferences, and likely in other systems as well; ask us about yours if you’re not sure.) Useful ham words include the name of your city, local high school or college names, club names or abbreviations, industry-specific terms, and any other words that are specific to your community or profession. Always test a possible ham word by first searching for it in your Spam folder to make sure it appears only in legitimate messages.

(Featured image by iStock.com/Fotosmurf03)

Choose Your Preferred Default Web Browser and Email App in iOS and iPadOS 14

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Since the earliest days of the iPhone, Apple’s Safari and Mail have been the default Web and email apps for iOS and, later, iPadOS. There was no way to choose alternatives that would be used whenever an app wanted to open a Web page or create an email message. That has now changed with iOS 14 and iPadOS 14. To switch to a different Web browser (such as Brave, DuckDuckGo Privacy Browser, Firefox, Google Chrome, Microsoft Edge, or Opera Touch) or a different email app (such as Boomerang, Chuck, Hey, Gmail, Outlook, Polymail, or Spark), follow these directions. In Settings, tap the name of the browser or email app you want to set as the default. Then tap Default Browser App or Default Mail App and select the desired app.

(Featured image based on an original by Sotiris Gkolias from Pexels)

Be Careful in iOS 13’s Mail App—the Trash Button Is Where Reply Used to Be!

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For unknown reasons, Apple redesigned the toolbar in the iOS 13 version of Mail. Such things happen, but this time, Apple made a big mistake and moved Mail’s Trash button to where its Reply button used to be. Lots of people who have become accustomed to tapping Reply are now finding themselves deleting messages inadvertently, since a tap in the same location in iOS 13 deletes the message. It’s hard to retrain muscle memory—the ability to reproduce a particular movement without conscious thought—but if you find yourself deleting messages accidentally, you’ll need to slow down and remember to tap the new location of the Reply button.

(Featured image by Skitterphoto from Pexels)

Want to Use Your Friends’ Nicknames in iOS? Here’s How

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If you have a friend whom you refer to only by his nickname, it can be annoying to feel like you should use his proper first name when adding him to Contacts. Worse, then he shows up in Messages with a name you don’t recognize as easily. Here’s how to convince iOS to use his nickname instead. Open his card in Contacts, tap Edit, scroll to the bottom, tap Add Field, and tap Nickname. That puts a Nickname field at the top, under his proper name, for you to fill in. To get iOS to use it, go to Settings > Contacts > Short Name and enable Prefer Nicknames. From then on, you can enter your friend’s nickname instead of his proper name in apps like Messages and Mail, and iOS will also display it instead of his name everywhere.

(Featured image by Yuri Manei from Pexels)

How to Get Custom Alerts for Email from Your VIPs

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Few people get so little email that they want an iPhone notification for every message that rolls in. But many of us have just a couple of people—our personal VIPs—whose messages are important enough to warrant an alert. If that’s true for you, and you want to know right away when your boss or your spouse or your child sends you a message, set up VIP Alerts. In Mail in iOS, in your Mailboxes list, tap the i button next to the VIP mailbox. If necessary, use the Add VIP link to pick your VIPs from your contacts, and then tap VIP Alerts to jump to the screen of Settings > Notifications > Mail > VIP. Once there, you can choose a banner style, alert sound, and other notification-related settings.

(Featured image by Noelle Otto from Pexels)

Choose between Archiving and Deleting Messages in iOS Mail

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When you’re viewing a message in Mail on an iPhone or iPad, you get five buttons: Flag, Move, Archive or Delete, Reply/Forward/Print, and New Message. But what determines whether that third button is Archive or Delete? iOS hides that option in Settings > Passwords & Accounts > YourEmailAccount—the details then vary by account type before you see the Move Discarded Messages Into options.

  • iCloud as your primary address: Mail (under Advanced) > Advanced
  • iCloud as a secondary address: Account > Mail > Advanced
  • Gmail or other email provider: Account > Advanced

But what if you want to archive a message when you have Deleted Mailbox selected, or vice versa? Simply tap and hold on the Archive or Delete icon, and a popover appears, giving you both choices.

Ever Wanted to Get a Custom Email Address? Here’s How (and Why)

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Some facts about ourselves are difficult or impossible to change, but your email address doesn’t have to be one of them. Switching to a custom email address might seem overwhelming, and it will take some time, but it’s not that hard or expensive (and we’re always happy to help if you get stuck).

Why Consider Switching to a Custom Address?

Why would you want to take on such a task? Independence. If you’re using the email address that came from your Internet service provider, you could end up in an awkward situation if you have to move and switch ISPs. Any address that ends in @comcast.net, @anything.rr.com, @verizon.net, @earthlink.net, or the like could be problematic. You also don’t want to rely entirely on a work email address—there’s no guarantee that your employer will forward email for you indefinitely if you take a different job.

Also, an email address says something about you, much as a postal address does—there’s a difference between an address on Central Park versus one in the Bronx. If you’re not happy with what your email address implies, you might want to switch.

What can an email address reveal? Those with a free Juno, Hotmail, or Yahoo account likely signed up years ago and don’t take email very seriously. People who use an @icloud.com, @me.com, or @mac.com address are clearly Apple users, and those with an address ending in @live.com, @msn.com, or @outlook.com are probably Windows users. .edu addresses identify students, teachers, and school employees—but if you’re not one anymore, your email looks like you’re wearing a varsity jacket in your 40s. The big kahuna of email is Gmail, which boasts about 1.5 billion users worldwide now—as a result, using a Gmail address is fairly generic.

The ultimate in independence comes when you register your own domain name, which usually costs less than $20 per year at sites like 1&1 Ionos, Domain.com, easyDNS, Directnic, and Register.com. Then your address can be anything you want at your new custom domain, and you never again have to worry about being tied to your ISP or associated with a free email host.

How to Change to a Custom Address

Step 1: Register a new domain name. The hard part here is thinking of a name that hasn’t already been taken. It’s best to stick with the traditional top-level domains like .com, .net, and .org—if you get into the new ones like .beer (yes, that’s available), your email is a bit more likely to be marked as spam. Most domain registrars will also host your email for you, and if you go this route, you can skip Step 2.

Step 2: If you’re already using Gmail or another independent email provider that isn’t tied to your ISP, log in to your account at your domain registrar and configure it to forward all email to your existing email address. In this case, you can skip Steps 3 and 4.

However, if you aren’t happy with your current email provider, you’ll need to set up an account with a new one. There are lots, but many people use a paid email provider like FastMail or easyMail that usually charges less than $50 per year and supports multiple mailboxes. When you set up the account, you’ll need to create one or more new email addresses at the provider and configure MX (mail exchange) records with your domain registrar—the service will provide instructions for this.

Step 3: If you’re changing email providers as part of this process, you’ll need to configure Mail—or whatever email client you’re using—to connect to your new email account with the login credentials you set up. That’s not hard, but being able to send email that comes from your custom address can require some effort with the free email providers. Gmail provides instructions, and others that support this feature will as well. Unfortunately, iCloud won’t let you send email using a custom address.

Step 4: If you’re moving to a new email provider, you’ll need to forward your mail from your old provider to your new custom address. Most email providers and ISPs have a screen somewhere in the account settings of their Web sites that lets you enter a forwarding address.

Step 5: Tell your family, friends, and colleagues about your new email address, and update mailing lists and accounts at sites like Amazon that send you email. The forwarding you set up in the previous step will ensure you don’t miss anything during the transition, but remember that if you cancel your old ISP account, that forwarding may end immediately, so it’s important to start the process well in advance.

The details will vary depending on your choice of domain registrar and email provider, so again, if you would like additional recommendations or assistance in setting all this up, just let us know.

Social Media: Setting up a custom email address with your own domain isn’t that hard or expensive, and it gives you independence from your ISP, employer, or the sketchy email provider you signed up with after college. Here’s how you can switch.