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When the Smiley Face Symbol Auto-Corrects to a Square in Outlook 2016

February 25, 2017

**** [NOTE: Two updates have been made to the middle and bottom of this post to help readers resolve their issue faster.] ****

A client recently came across an odd situation and I thought I’d share some ideas for solutions if this happens to you:

What: 

When writing an email in Microsoft Outlook, they would type a colon and a right bracket, they expect to see a happy face emoticon appear.

Unfortunately something had happened to their PC and now a : and ) no longer made a smiley face ; rather, it made a square.

If they pressed CTRL + Z, they could get a : ) but it wasn’t nearly as nice as a happy little round symbol. 🙂

emoticon-symbol-smiley

So What:

The ability to use smiley faces in their email correspondence in Outlook 2016 was important to them.

They put happy faces in almost every email they write because they find emails can come across as cold without the added visual context.

I totally get this! My email tone is often interpreted as angry, frustrated, or rude when I’m just focused on getting to the point in the fewest number of words possible.

happy-face

What Next:

The internet was not very helpful. The closest thing to a potential answer that I found is this TechNet Forum Post.

I came across a short list of troubleshooting steps that a user should work through one at a time to see if the issue can be resolved.

Some things to consider:

#1 – Check the format of your emails in Outlook.

Open a new email > Format Text > Format > set to HTML or Rich Text (Plain text = no formatting, emoticons, or symbols will work).

outlook-2016-square-emoticon-01

#2 – Check AutoCorrect to see what it is set to replace : )  in Outlook.

How: In Outlook > File > Options > Mail > Spelling and AutoCorrect > AutoCorrect Options > check the list in AutoCorrect to see if it is set to replace : ) with J.

**** UPDATE #1: If you see a smiley face here, but you’re still seeing a square in your emails then please follow these step-by-step instructions from fellow Blogger Robert S. carefully: Colorful emoticons and smiley faces in Outlook. ****

**** UPDATE #2:  Eileen P. points out: “It doesn’t work to copy/paste the smiley symbol or emoji into the AutoCorrect dialog box. You have to *selected it in a newly created email* and then open the AutoCorrect dialog and tell it what you want that symbol to replace.” ****

outlook-2016-square-emoticon-02

#3 – Check Display Email Content settings in Outlook.

How: File > Options > Mail > Editor Options > Advanced > Look for the “Display e-mail content” header and ensure that “Show picture placeholders” is not checked.

outlook-2016-square-emoticon-03

#4 – Check Trust Center settings in Outlook.

How: File > Options > Trust Center > Trust Center Settings > Automatic Download and ensure that “Don’t download pictures automatically in HTML e-mail messages or RSS items” is not checked.

outlook-2016-square-emoticon-04

 

If that didn’t work… let me know! Here are some other ideas to consider:

  •  Did you delete the Wingdings font from your machine at some point?

Update – March 6, 2017: My friend Robert Sparnaaij, MVP Outlook, contacted me and explained that this issue can happen for folks with versions of Windows that do not support system wide emojis. People that are affected by this issue can recreate the AutoCorrect entries with the Wingdings font (as I suggested) or better yet use colorful images of their own. He has a post on his MSOutlook.info blog that thoroughly explains how to Add new smileys, icons and logos to AutoCorrect – check it out: Colorful emoticons and smiley faces in Outlook

Update – March 10, 2017: Community member Eileen P. shared her insights in this blog post’s comments section: “Here’s what I realized: It doesn’t work to copy/paste the smiley symbol or emoji into the AutoCorrect dialog box. You have to *selected it in a newly created email* and then open the AutoCorrect dialog and tell it what you want that symbol to replace. Follow the link that Kelly added in her update and follow the instructions carefully.” Thank you Eileen!

15 Responses

  1. Eileen says:

    Hi, I’m having this issue and I’m stuck on your #2. According to my AutoCorrect settings, the smiley is being replaced by … an asterisk. ALL of the faces are replaced by asterisks. Except what they are actually replaced by is the square (as you described).

    This is not only happening in Outlook 2016 but also in Word 2016.

    It started happening after I uninstalled Office 2013 and installed Office 2016.

    I tried this: I opened a Word document, inserted the Wingding symbol for smiley face, and tried to copy/paste it into Outlook’s AutoCorrect settings as what to replace 🙂 with. But when it’s in the table, it still looks like an asterisk. ???

  2. shania a says:

    Hi! I have tried all settings on this list of instructions, as well as the suggested link above for “colorful emojis” but nothing is working. Whenever I type a 🙂 it still shows an empty box. I made sure all my settings were listed the way informed above… help?!

  3. Nathan says:

    Was any solution found to repairing a once working installation?
    I have 2 users now who both have office 2016, and both have them have noticed that in the last week their smiley emoji’s (and a couple of others) no longer work.

    Some do work though, and they were all working at some point which to me rules out your friends idea of it being the OS.

    I like yourself have searched for days without any luck. Only thing I haven’t tried which i can think of is maybe recreate the normal.dotm file??

  4. Shelly says:

    I figured it out! Thank you!

  5. Eileen says:

    Here’s what I realized: It doesn’t work to copy/paste the smiley symbol or emoji into the AutoCorrect dialog box. You have to *selected it in a newly created email* and then open the AutoCorrect dialog and tell it what you want that symbol to replace. Follow the link that Kelly added in her update and follow the instructions carefully.
    Hope this helps.

    • Thank you for taking the time to provide your insight and sharing it with the group, Eileen. I will update the post and add your comment to help others solve their issue faster!

  6. Crystal says:

    When creating/replacing the smiley face in the auto correct dialog, the happy smiley is the ONLY one that it will not let me change from plain text to formatted text. The option is just grayed out and nothing I do will make it clickable. 🙁 All of my other smileys still show the option.

  7. depeters says:

    Had one client with this issue and tried all of the suggestions above. Heres what worked for me.
    Start a new email message, click on Insert tab at top, put your cursor inside the message and then you will see Symbol on the right side of menu, click on it then select More Symbols at the bottom. On the Symbols tab check that the Font selected is Windings and not something else. Wingdings is the source of the smileys and if its not selected your program wont recognize it.

  8. Mario says:

    Just FYI, if you are in the Symbol dialog from item #3 above, there is a box in the lower left called “Autocorrect…” that will take you to the same dialog box where you can replace the square with a smiley face from the Wingdings font.
    This also just started happening to me on one computer running Office 2016. Works fine on another running Office 2013.

  9. Tracy Sulkin says:

    I’m not sure if someone already posted this. It’s an easy fix in Windows 7. Maybe it’ll work with later versions.

    1. Open a new email message.
    2. Insert–Symbol–More symbols
    3. In the symbols box, change the font to Wingdings.
    4. Click the happy face to highlight it
    5. Click auto-correct (at the bottom of the box).
    6. In the auto-correct box, the happy face will be in the ‘With’ field box under ‘Replace text as you type’
    7. Type a colon & close-parenthesis in the ‘Replace’ field box.
    8. Click okay.

    All fixed.

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Kelly Marshall

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