How to Stop Outlook from Automatically Converting Emoticons into Emojis

When typing professional emails, technical instructions, code documentation, or mathematical formulas in Microsoft Outlook, standard punctuation combinations such as :) or ;) are frequently transformed into bright, colourful graphic emojis without your permission. While graphical smileys might be appropriate for casual conversations, automated emoji substitution can disrupt formal business communication, alter source code syntax, and frustrate authors who prefer plain typographical characters.

This automated behaviour is powered by Outlook’s built-in AutoCorrect dictionary, which is inherited from Microsoft Word’s proofing engine. In this guide, you will learn how to permanently stop Outlook from converting text emoticons into graphical emojis, as well as how to selectively undo replacements on the fly.

Why Disable Automated Emoticon Replacement in Outlook?

Disabling graphical emoji replacement ensures greater control over your email composition:

• Maintains professional standards: Corporate communications often require a neutral, formal tone where cartoon smiley faces can look out of place.
• Prevents technical syntax corruption: Punctuation sequences in file paths, terminal commands, regular expressions, or programming snippets can trigger unwanted emoji substitutions.
• Eliminates cross-client rendering inconsistencies: Different email clients (such as Apple Mail, Thunderbird, or mobile apps) render graphical emojis in diverse and sometimes unpredictable styles. Plain ASCII text emoticons render reliably on every device.

How to Stop Outlook from Replacing Emoticons with Emojis Permanently

To eliminate automatic emoticon replacement in the classic desktop version of Microsoft Outlook on Windows:

1. Launch Microsoft Outlook on your computer.
2. Click the File tab in the upper-left corner of the window.
3. Select Options from the left-hand navigation pane to open the Outlook Options dialogue box.
4. In the Outlook Options window, click on Mail in the sidebar.
5. Under the Compose messages section, click the Editor Options… button.
6. In the Editor Options window, click Proofing on the left, then click the AutoCorrect Options… button located near the top.
7. In the AutoCorrect tab, inspect the list under Replace text as you type.
8. Scroll through the alphabetical list or type :) into the Replace box to locate the entry.
9. Select the smiley entry that replaces :) with a graphic emoji, and click the Delete button.
10. Repeat this step for any other emoticon triggers you wish to disable, such as :(, ;), or :-D.
11. Click OK on all open dialogue windows to save and apply your configuration.

Once deleted from the AutoCorrect table, Outlook will preserve your exact keystrokes whenever you type emoticon punctuation strings.

How to Undo Emoji Replacement on the Fly

If you prefer to keep AutoCorrect enabled for general typing but occasionally want to retain a plain text emoticon in a single email:

• Use the Undo Shortcut: Immediately after typing :) and pressing the Spacebar (which triggers the replacement), press Ctrl + Z (or Cmd + Z on macOS). Outlook will revert the graphical emoji back to the literal text emoticon while keeping your subsequent text intact.
• Hover over the Replacement Indicator: Hover your mouse cursor over the inserted emoji until a small blue bar appears beneath it. Click the drop-down icon and choose Change back to “:)” or Stop Automatically Correcting “:)”.

Preventing AutoCorrect Formatting in the New Outlook and Outlook on the Web

If you are using the modern web-based “New Outlook for Windows” or Outlook on the Web (outlook.office.com):

1. Click the Settings gear icon in the top right header.
2. Navigate to Mail > Compose and reply.
3. Scroll down to the Microsoft Editor or Proofing section.
4. Select Editor Settings and review the Punctuation and Formatting options to turn off automated text substitutions.