How often do you send an email only to realize you forgot to say something or attach a file? Or you think of something to say late at night and want your recipient to receive it in the morning after they’re awake?

And what about those times you want to remember whom you emailed recently who hasn’t responded? Or get reminded to reply to a message you discovered at an inopportune moment?

All of these concerns are addressed by new features of Mail in macOS Ventura and iOS/iPadOS 16. Sure, they’ve been available in other email applications before, but it’s great that Apple has given them new light in Mail, its first party app that comes with every Mac, iPhone, and iPad.

Undo Send

Suppose you just emailed your friend birthday greetings only to realize their birthday is actually tomorrow. You can have Mail delay sending an email during which time you can undo the send. This will bring you back to the compose window where you can edit the message.

In Mail > Preferences > Composing > Undo send delay on Mac and Settings > Mail > Undo Send Delay on mobile, you can specify 10, 20, or 30 seconds (or turn off the delay entirely).

Send Later

So, it turns out you didn’t actually miswrite the message. You just wanted to send it tomorrow instead. Mail can do that, too.

Click the popup menu next to the Send button on the toolbar on Mac or long-press the Send button on mobile to reveal the Send Later choices.

You can choose from standard choices for today or tomorrow, or pick your own date and time on the calendar. Your device just has to be online. (On your Mac, Mail also has to be open, even if its windows are closed.)

Followup Suggestions

Remember how you sent those birthday greetings a few days ago and never heard back. You asked how your friend was celebrating, right? That’s why Mail intelligently put the sent email back in your inbox, reminding you to follow up on the extravaganza that ensued.

In Mail > Preferences > General on Mac, you can toggle Enable message follow up suggestions; in Settings > Mail on mobile, it’s just Follow Up Suggestions. You can also add a Follow Up mailbox to your Favorites for quick access to all these suggestions.

Reply Reminders

While you have no direct control over which sent messages Mail invites you to follow up on or when, you can have it remind you to act on messages you’ve received.

On Mac, choose Message > Remind Me or right-click a message and choose Remind Me; on mobile, swipe right on a message and choose Remind Me.

Again, you can choose from a few standard times or pick any date and time you like. Reminder emails are stored in a Remind Me mailbox in Mail, not synced with your Reminders in that other app.

Forgotten Attachment

If the wording of your email message indicates you intend to attach something and you send without doing so, Mail may catch you in the act and invite you to resolve your error. Choose Cancel to return to the message (so you can add the attachment) or Send Anyway if all is well.

With all these improvements, Mail has become quite a complex application, but it offers them elegantly. To discover new features, do you feel you have permission and the freedom to explore and figure it out? You do!

Take some time to mouse over the toolbar, click on the menus, and realize what happens when you swipe or long-press. Then, let me know when you get lost or have questions.