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Colorful emoticons and smiley faces in Outlook

This might be a touchy subject for fanatic or business level Outlook users but I wanted to ask this anyway.

I know that Outlook supports emoticons as when I type :-) Outlook converts it to and it also does this for :-( and :-|. However, these are of course very old fashioned looking and quite limiting in choice.

I could insert an image each time, but an autoconvert feature such as in Windows Live Messenger and Skype would be better.

Anyway, how can I improve Outlook’s emoticon support?

This is indeed a touchy subject for some core Outlook users but also quite a common request from the more casual Outlook users or home users who converted from IncrediMail to Outlook.

Even though Outlook doesn’t offer native support for custom and colorful smileys, it is easy to set this up via AutoCorrect. This way, smileys will directly convert from their textual counterpart to an icon of your choice.

In fact, the built-in conversion of :-) to emoticon smiley is also done via AutoCorrect.

Via AutoCorrect you can replace Outlook's dull emoticons will colorful new ones and add new ones of your own as well.
Via AutoCorrect you can replace Outlook’s dull emoticons will colorful new ones and add new ones of your own as well. (Due to a bug in Outlook/Word the image may not always show in the AutoCorrect dialog.)

Adding new smileys, icons and logos to AutoCorrect

In the example above I’ve used an emoticon from the MSN webpage.

  1. Create a new message.
  2. Insert the image or symbol of choice either from disk, the web or from a symbol font such as Wingdings. (See the bottom of this guide for more info on this.)
  3. Select the inserted image or symbol.
  4. Open the AutoCorrect options dialog;
    • Outlook 2003 and previous (requires Word as your email editor)
      Tools-> AutoCorrect Options…
    • Outlook 2007
      Office logo at the top left corner-> Editor Options-> Proofing-> button AutoCorrect Options…
    • Outlook 2010 and Outlook 2013
      File-> Options-> Mail-> button: Spelling and Autocorrect…-> button: AutoCorrect Options…
  5. Select the AutoCorrect tab.
  6. Type your characters that should convert into this image in the “Replace” field.
    For instance :-) or :-P
  7. Verify that the “With” option is set to “Formatted text”. You may not see your image in the box below it (this is a small bug in Outlook).
  8. Click the button Add or Replace (in case the entry already exists).
  9. In the list below, you’ll now see an entry for your typed characters. The asterisk (*) indicates that it will be replaced with an image.
  10. Press OK until you’ve returned to your message.

After you’ve configured the emoticon, the next time that you want to insert it, simply type your emoticon in characters and it will be replaced with your image (you might need to press the Spacebar or ENTER afterwards for it to actually convert).

Note 1: Outlook doesn’t offer support for animated gifs, but it the message is received by a mail client which does, the gif image will still animate. For more info see; Making gifs animate.

Note 2: If AutoCorrect is not available for you see Automatic spell check and Autocorrect not working.

Easy access to AutoCorrect options

When setting up your emoticons, quicker access to the AutoCorrect options dialog might be handy in Outlook 2007 and Outlook 2010. For this you can add the command to the Quick Access Toolbar (QAT).

Adding the AutoCorrect Options button to the QAT can significantly speed up the configuration of custom emoticons.
Adding the AutoCorrect Options button to the QAT can significantly speed up the configuration of custom emoticons.

Backup your AutoCorrect entries

Once you’ve configured your custom emoticons, you might want to create a backup of them. To do this, make a copy of your normal.dot (Outlook 2003 and previous) or normalemail.dotm file when Outlook is closed (for Outlook 2003 and previous, Word needs to be closed as well).

You can find the file here;

  • Windows XP
    C:\Documents and Settings\%username%\Application Data\Microsoft\Templates\
  • Windows 8, Windows 7 and Windows Vista
    C:\Users\%username%\AppData\Roaming\Microsoft\Templates

Note: For more locations and files in which Outlook stores its data and settings see the guide; Files and Settings guide for Outlook.

Source of a new smiley, icon or logo

You can use basically anything as a source for your new emoticon;

  • An image from your hard disk.
    Insert-> Picture
  • An image copied from a web page.
    To insert an image directly from a webpage, right click on the image, choose Copy and paste it in your message (CTRL+V).
  • A symbol from a font such as Wingdings.
    When you inserted a symbol from a font, you can enlarge it and apply a color to it.


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