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Press Windows key + . (period) on Windows, or Control + Command + Space on Mac, to open the system emoji picker wherever your cursor is. This works in Outlook and in essentially every other application, which makes it the fastest method by a wide margin.
Method 1 — the keyboard shortcut (fastest)
The picker stays open for multiple insertions, and it includes GIFs, symbols and kaomoji on Windows.
Method 2 — Outlook's built-in emoji button
In new Outlook and Outlook on the web, while composing a message look for the smiley face icon in the formatting toolbar at the bottom of the compose window. Click it, browse or search, and click one to insert. If you don't see it, click the three dots (⋯) in the toolbar to reveal hidden options.
In classic Outlook for Windows, go to the Insert tab, then Symbols → Symbol for basic characters, though the emoji selection there is limited compared with the system picker.
Method 3 — autocorrect shortcuts
Outlook converts some text combinations automatically as you type:
| Type | Get |
|---|---|
:) | 🙂 |
:( | 🙁 |
;) | 😉 |
:D | 😀 |
:| | 😐 |
<3 | ❤ |
This relies on AutoCorrect being enabled, under File → Options → Mail → Spelling and Autocorrect → AutoCorrect Options. You can add your own entries there too.
Method 4 — copy and paste from any emoji reference site. Reliable, if inelegant.
On the Outlook mobile app, just use your phone's normal keyboard emoji key — there's nothing Outlook-specific about it.
Reacting to an email with an emoji is different from inserting one. In new Outlook and Outlook on the web, hover over a received message and click the thumbs-up or smiley reaction icon in the top right of the reading pane. Reactions are visible to others on the thread and work best within the same organisation.
If emojis appear as boxes or question marks, the recipient's client can't render that character. This is most common with:
Sticking to widely supported, older emoji avoids nearly all of this.
A note on professional use: emoji are increasingly normal in internal email but still read as informal externally. A thumbs-up in a reply to a colleague is fine; a string of emoji in a first email to a client generally isn't. Also worth knowing that some emoji render differently across platforms, and a few carry meanings you may not intend.
Keyboard shortcut not working? On Windows, the picker needs Windows 10 or later. If nothing happens, check that the touch keyboard service is running, or search for "emoji" in the Start menu. On Mac, the shortcut can be reassigned under System Settings → Keyboard → Keyboard Shortcuts.