Text Formatting & Scheduling in Messages on macOS Sequoia

This guide shows you how to use the new text formatting options (bold, italic, underline, strikethrough) and message scheduling in the Messages app on macOS Sequoia. You’ll learn the exact steps to format your text and send messages at a later time, plus common pitfalls and troubleshooting tips.

What You’ll Need

• A Mac running macOS Sequoia (14.0 or later).
• The Messages app updated to the latest version (it updates automatically with the OS).
• An active iMessage account (for scheduling) or SMS/MMS (formatting works on both, but scheduling may be limited to iMessage).

Step-by-Step

Part 1: Text Formatting

1. Open Messages from the Dock or Applications folder.
2. Start a new message or open an existing conversation.
3. Type your text in the message input field at the bottom of the window.
4. Select the text you want to format by clicking and dragging over it, or double-clicking a word.
5. Look for the formatting bar that appears above the selected text. It shows icons for Bold (B), Italic (I), Underline (U), and Strikethrough (S).
6. Click the desired icon to apply the formatting. You can combine multiple formats (e.g., bold and italic).
7. If the formatting bar doesn’t appear, press Command+B for bold, Command+I for italic, Command+U for underline, or Command+Shift+X for strikethrough.
8. Send the message as usual by pressing Return or clicking the send button.

Part 2: Scheduling Messages

1. Compose your message as you normally would in the input field.
2. Do not press Return yet. Instead, look for the small plus (+) icon to the left of the input field, or the up arrow next to the send button (the exact icon may vary slightly by version).
3. Click the plus icon to reveal a menu. Select “Send Later� or “Schedule� (wording may differ).
4. Choose a date and time from the pop-up calendar and clock. You can pick a preset like “Tonight� or “Tomorrow,� or set a custom time.
5. Confirm the schedule by clicking “Schedule� or “Done.� The message will now show a small clock icon next to it.
6. To edit or cancel a scheduled message, hover over the message bubble in the conversation, click the clock icon, and choose “Edit� or “Cancel.�
7. Note: Scheduling works best with iMessage. For SMS/MMS, the feature may be unavailable or require the recipient to have iMessage enabled.

Common Mistakes

• Formatting not applying: You might be trying to format text that is already sent. Formatting only works on text before you send it.
• Scheduling without the plus icon: If you don’t see the plus icon, you might be in an SMS conversation. Scheduling is only available for iMessage.
• Setting the wrong date/time: Double-check the time zone and AM/PM. macOS uses your local time zone, but if you travel, the scheduled time may shift.
• Forgetting to confirm: Some users type a message, click the plus, but don’t click “Scheduleâ€� – the message stays as a draft. Always confirm the schedule.
• Using formatting in group chats: Formatting works in group chats, but some older devices may not display it correctly. Stick to plain text for critical messages.

Tips

• Use formatting sparingly: Bold for emphasis, italic for tone, underline for links (though links are auto-detected), and strikethrough for edits.
• Schedule time-sensitive messages: For example, a “Happy Birthdayâ€� message at 9 AM, or a reminder for a meeting.
• Combine formatting with scheduling: You can format your text first, then schedule the message – both features work together.
• Check the recipient’s device: Formatting may not appear correctly on older iOS versions or Android devices (for SMS).
• Use keyboard shortcuts: They are faster than clicking the formatting bar. Learn them to speed up your workflow.

Troubleshooting

• Formatting bar doesn’t appear: Make sure you have selected text. If it still doesn’t show, try using the keyboard shortcuts (Cmd+B, etc.). If those don’t work, restart Messages or your Mac.
• Scheduling option is grayed out: This usually means you’re not connected to iMessage. Go to Messages > Settings > iMessage and ensure you’re signed in. Also check that the recipient has iMessage enabled.
• Scheduled message didn’t send: Check that your Mac is on and connected to the internet at the scheduled time. If it was off, the message will send when you next open Messages.
• Can’t edit a scheduled message: You can only edit a scheduled message before it sends. After it sends, it’s like a normal message – you can’t edit it (only delete for everyone within 2 minutes).
• Formatting shows as plain text: If the recipient sees plain text, their device may not support rich text. Try sending a test message to another Apple device to verify.

Frequently Asked Questions

1. Can I schedule a message to a non-iMessage contact? No, scheduling is only available for iMessage. For SMS/MMS, you’ll need to send it manually.
2. Does formatting work in group chats? Yes, formatting works in group chats, but the appearance may vary depending on each participant’s device and OS version.
3. Can I cancel a scheduled message after it’s sent? No, once sent, it’s a regular message. You can only delete it for everyone within 2 minutes of sending.
4. Why don’t I see the formatting bar? The formatting bar appears only when you select text. If it still doesn’t appear, check that you’re running the latest version of macOS Sequoia.
5. Can I schedule a message for a specific date in the future? Yes, you can set any date and time, not just presets. Use the custom date picker.
6. Will formatting work if I send to an Android phone? For SMS/MMS, formatting is usually stripped and sent as plain text. For iMessage to Android (via SMS), it won’t show.

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