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Outlook does not use one universal emoji shortcut on every platform. The quickest method depends on whether you use Outlook on Windows, Outlook for Mac, classic Outlook, or Outlook on the web.
Here are four reliable ways to insert an emoji into an Outlook message: use the Windows emoji picker, open the macOS character viewer, type an emoticon and let AutoCorrect convert it, or install an emoji add-in.
1. Use the Windows emoji picker
On a Windows PC, the built-in emoji picker is usually the fastest option. It is a Windows text-entry feature, not a special Outlook ribbon command.
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- Open a new email or reply in Outlook.
- Click in the message body so the text cursor is visible.
- Press Windows key + . (period).
- Select an emoji from the panel.
- Select the × button to close the picker, or continue typing.
You can scroll through the available characters, select a category icon, or search by keyword. For example, type present in the picker to filter the results.
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Microsoft lists this method for Outlook for Microsoft 365, Outlook 2024, Outlook 2021, Outlook 2019, and Outlook 2016 when running on Windows 10 or Windows 11.
If Windows + period does nothing
Make sure the cursor is active in the email body. If Outlook focus is still on the To, Subject, folder list, or another control, the picker may open without inserting the emoji into your message—or may not open at all.
The shortcut is supplied by Windows, so it is not controlled by an Outlook keyboard-shortcut setting. Windows 10 still runs after Microsoft ended support on October 14, 2025, but it no longer receives free Windows Update software updates, technical assistance, or security fixes from Microsoft.
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Outlook for Mac uses the macOS emoji and symbol viewer. The shortcut is different from the Windows command:
Control + Command + Spacebar
- Open a new message or reply in Outlook for Mac.
- Click inside the editable message area.
- Press Control + Command + Spacebar.
- Choose an emoji from the viewer, or search for one by name.
Microsoft lists this shortcut for Outlook for Microsoft 365 for Mac, Outlook 2024 for Mac, and Outlook 2021 for Mac.
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Do not use Command + Control + Spacebar as a Windows Outlook shortcut. That command belongs to the Mac instructions; Windows uses Windows key + period.
When the Mac shortcut fails
The cursor must be in an editable part of the message. The shortcut can also be affected by macOS keyboard settings or a third-party utility that has assigned the same key combination. Check those assignments if the character viewer does not appear or another action occurs instead.
3. Type an emoticon and let AutoCorrect replace it
Classic Outlook desktop can convert familiar text emoticons into Unicode color emojis as you type. This is useful when you only need a smile, wink, heart, or similar symbol and do not want to open a picker.
These are the emoticons Microsoft documents for conversion:
| Type | Typical result |
|---|---|
:) or :-) |
Smiling face |
:-| or :| |
Neutral expression |
:( or :-(' |
Sad face |
:D or :-D |
Grinning face |
:p or :-p |
Face with tongue |
:o or :-o |
Surprised face |
;) or ;-) |
Winking face |
<3 |
Heart |
</3 |
Broken heart |
For example, type :-) followed by a space or punctuation. Outlook can replace it with a Unicode emoji rendered using the Segoe UI Emoji font. Microsoft identifies the smiley face as Unicode character U+1F60A.
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This behavior is documented for Outlook for Microsoft 365, Outlook 2024, Outlook 2021, Outlook 2019, and Outlook 2016.
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If Outlook changes an emoticon when you did not want it changed, press Ctrl+Z immediately. The replacement should revert to the characters you typed.
Check or disable emoji AutoCorrect
In classic Outlook for Windows:
- Select File > Options.
- Choose Mail.
- Select Editor Options.
- Open Proofing.
- Select AutoCorrect Options.
- On the AutoCorrect tab, check Replace text as you type.
To disable one particular conversion, enter its punctuation string in the Replace box, select the matching entry, and choose Delete.
Why the emoticon stays as text or becomes a box
- If
:)or another string remains unchanged, the relevant AutoCorrect entry may be disabled or missing. - If the result appears as an empty square or box, the Segoe UI Emoji font may be missing or damaged. Microsoft says this font is included with Windows 8 and later.
Older guides may tell you that Outlook uses a black-and-white Wingdings character such as F04A. That describes older Office and Windows behavior. Current documented Outlook behavior uses Unicode emoji and Segoe UI Emoji instead.
4. Add an emoji add-in
An add-in can provide its own emoji panel or insertion controls inside Outlook. This is worth considering if the built-in picker is unavailable or you need features supplied by a particular add-in.
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- Open the Outlook message window.
- Select Home > Get Add-ins.
- Search for Emoji.
- Choose an add-in and select Add.
- Follow that add-in’s instructions to open its panel and insert a character.
There is not one universal Microsoft-built-in Emoji add-in with a guaranteed interface. Search results, controls, and capabilities can vary by the current add-in catalog and by your organization’s Microsoft 365 administration.
In a managed work account, Get Add-ins may be hidden or restricted. Microsoft’s emoji instructions do not provide an administrator-bypass workaround. If the store is blocked, use the Windows picker, Mac character viewer, or AutoCorrect instead.
Which method should you use?
| Situation | Best choice |
|---|---|
| Outlook on Windows | Windows key + period |
| Outlook for Mac | Control + Command + Spacebar |
| You repeatedly use simple smileys or hearts | Type an emoticon and use AutoCorrect |
| You need an add-in’s special emoji controls | Home > Get Add-ins |
| Outlook on the web or new Outlook and no picker shortcut works | Use the operating system’s emoji picker, or an available add-in |
What about Outlook on the web and new Outlook?
Microsoft distinguishes new Outlook for Windows from classic Outlook. In Outlook for Windows, the presence of a Settings option on the ribbon indicates the new interface; without it, Microsoft directs users to the classic Outlook instructions.
Microsoft’s general Outlook shortcut documentation covers Outlook for Microsoft 365, Outlook 2024, Outlook 2021, Outlook 2019, Outlook 2016, Outlook.com, new Outlook for Windows, and Outlook on the web. It does not document one universal Outlook-specific Windows or web shortcut named “insert emoji.”
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- Outlook.com and new Outlook on the web: Settings > General > Accessibility > Keyboard shortcuts, select a shortcut scheme, then choose Save.
- Classic Outlook on the web: Settings > Mail > General > Keyboard shortcuts > Save.
Those settings control Outlook navigation shortcuts; they are not an emoji-insertion setting. In a browser, the operating system picker is generally the practical keyboard method: click in the message body first, then use the Windows or macOS command for your computer.
FAQ
What is the Outlook emoji shortcut on Windows?
Click in the email body and press Windows key + . (period). Select an emoji from the Windows picker, then close it with the × button if needed.
What is the emoji shortcut in Outlook for Mac?
Click in an editable message area and press Control + Command + Spacebar. This opens the macOS emoji and symbol viewer.
Why does Windows key + period not insert an emoji in Outlook?
The message body may not have focus. Click where you want the emoji to appear and try again. The shortcut works during text entry and comes from Windows rather than an Outlook ribbon command.
How do I stop Outlook from changing 🙂 into an emoji?
In classic Outlook, go to File > Options > Mail > Editor Options > Proofing > AutoCorrect Options. Find the matching entry and select Delete, or turn off Replace text as you type.
Can I undo an AutoCorrect emoji conversion?
Yes. Press Ctrl+Z immediately after Outlook converts the emoticon.
Why is my Outlook emoji showing as a square box?
The Segoe UI Emoji font may be missing or damaged. If emoticons also remain unchanged, the relevant AutoCorrect entry may be disabled or missing.
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The Bottom Line
For Windows, click in the message body and press Windows key + . For a Mac, press Control + Command + Spacebar. If you prefer typing, Outlook’s AutoCorrect can turn strings such as :-), ;), and <3 into Unicode emojis. Add-ins are an optional fourth route, but their availability and features depend on Outlook and your organization’s settings.
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