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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:


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. 🙂


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.


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).


#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.” ****


#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.


#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.



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 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!

59 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. ???

    • Oh yes, in #2, I didn’t get into the solution in step-by-step detail. Actually here is a great blog post by a Microsoft Outlook MVP that explains why and has very detailed step-by-step: Let me know if that helps! – Kelly

      • Eileen says:

        Hey! That worked! Thank you so much! 🙂

        • Glad to hear it! I updated the blog post to include that link at the bottom as another resource to solve the issue.

          • Shelly says:

            I can no longer type 🙂 and have the smiley come up. Went through your instructions under #2, found an old smiley to copy and paste under “Replace”, but it doesn’t change it. Why all of a sudden this is happening now?

    • Erik says:

      The “Update – March 10, 2017:” solved the problem for me.
      Start a new email, insert the emoji you want, then go into options until you get to the auto correct dialog box. At that point, the emoji you selected should already be showing in replacement box. All you need to do is they the keys you want it to replace.

      • Lara N. says:

        Erik’s suggestion of inserting the smiley face via the insert symbol command, and then replacing the auto-correct seems to have worked for me.

    • Rachel says:

      Lifesaver! This really helped me fix my issue.
      Thank you so much!

    • Rachel says:

      Thanks for this! It was driving me mad when I kept getting a stupid little box. Lifesaver!

    • Laura Floeckher says:

      Hi. I found that if I close all my Office programs, go to %appdata%\Microsoft\Office, rename my acl files (to have a different extension), then open Word, the autocorrect file recreates itself. My smilies were fixed after that.

  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.

    • Natalie says:

      This is what finally worked for me!

    • Simon says:

      This is the only think that worked for me. None of the other Autocorrect suggestions properly changed the font to Wingdings as well as replacing the character.
      Thanks 🙂

  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.

    • Nannette says:

      Thank you — this was what I needed. Smiley is back! 🙂

    • Anders says:

      Thanks a lot!

    • Sarah P. says:

      This worked, thank you!!!

    • Alyssa says:

      Thank you! This worked for me!!

    • bdwilcox says:

      Tracy’s instructions almost worked for us but one more step was necessary to fix it. Before Word’s AutoCorrect would take a new auto-correct assignment for 🙂 we first had to delete the existing association. Then it worked without issue. So what we had to do:

      1. Open a new email message.
      2. Insert tab > Symbol > More symbols
      3. Click the AutoCorrect… button (at the bottom of the box).
      4. Highlight the existing smiley face association then the Delete button then the OK button then the Close button (you should now be back at the new email)
      5. Again, Insert tab > Symbol > More symbols
      6. In the symbols box, change the font to Wingdings.
      7. Click the happy face to highlight it
      8. Click the AutoCorrect… button (at the bottom of the box).
      9. In the auto-correct box, the happy face will be in the ‘With’ field box under ‘Replace text as you type’
      10. Type a colon & close-parenthesis in the ‘Replace’ field box.
      11. Click the OK button then the Close button.

      That worked for us.

      • bdwilcox says:

        BTW, we had this happen to multiple PCs at work and all had Wingdings properly installed. Must have been an Office or Windows update that broke the functionality or corrupted something. Also tried deleting both Normal.dotm and NormalEmail.dotm from %AppData%\Microsoft\Templates so their respective programs could recreate them fresh and that didn’t fix anything.

      • Ayesha says:

        BDWilcox – you’re the BOSS!!!

    • Jen Newmeyer says:

      This worked for me. But now, in Office 365, I guess I won’t have the yellow smiley face anymore. Better than just a block I suppose.

    • Robert Castro says:

      Thank you! After trying everything here (and on other sites/forums) for what seems like days, your solution is what finaly did it for me on Office 2016. Very much appreciated!

    • Marcus says:

      Thank you. That was the correct way. I saw the auto correction for 🙂 were two stars (**). Happened with all the other smileys. But your way helped. Just need to find out how to change 😛 😮 etc. to correct smileys since Wingdings does not have such smiley replacements.

    • Sam says:

      Yes! This fixed my issue.

      None of the above changed to the outlook settings worked for me. Didn’t even have access to the Display subset of the Editor settings.

      When I changed the smiley through copy and paste, the message font would change to Wingdings after a smiley and I’d have to manually change it back.

      Doing it this way, through the symbol menu, has fixed everything.

      Thank you!

    • WL says:

      this is great! all worked for my Office 2016 on Windows 7 thanks!

  10. Thanks for this tutorial, it’s very useful.

  11. Akiko says:


    My entire office and I were having this same issue, and the above did and didn’t work out…

    I could not just change my autocorrect options by going the normal way (Options >> Mail >> Spelling and Autocorrect >> Autocorrect Options).

    But what I COULD do, and what I did do to solve the problem was a combo of the article above, and the comments below:

    1. Open a New Email
    2. Click “Insert” at the top, and go to “Symbol”
    3. Click on “More Symbols”
    4. Scroll to font “Wingdings”
    5. Find the Happy Face Emoji and click on it
    6. Click on “AutoCorrect…” while the happy face is still highlighted
    7. In the right hand box, you should see the happy face emoji; on the left box, you should see an area where you can type — type in a smiley there
    8. Click “Replace” –It might say “An AutoCorrect entry already exists. Do you want to redefine it?”–Press “Ok”

    That should work going forward. If it doesn’t, then make sure the above is correct (that your version can even view regular Wingdings/ Symbols, and that your text is not set to “Plain Text”)

    Good luck!

  12. Sam says:

    Worked for me

  13. Mark says:

    When I look at the Autocorrect options in Outlook, all my smileys are “locked”.

    I can’t change them, and they all show squares. Notice how they all have ** instead of a symbol? I tried the suggestions on this blog and several others and I can’t get to work.

  14. Hilde Aarflot says:

    Tracy Sulkin’s solution works both with Outlook and with Word:)

  15. Osman says:

    Dear Kelly,

    This is what i was looking for exactly. You explain the solution very understandable and meticulous. Thans you made my day 🙂

    It’s amazing when you find the solution for a very specific case such as “Square instead of smiley emoji”

    • Thank you Osman! I was struggling to find answers for the phrase “Square instead of smiley emoji” myself, which is why I wrote the post. I may not be clever enough to come up with the solution to the issue on my own, but I can point to those who have posts that do, and help people in the process.

  16. Scott says:

    Just had this happen to me after an update to O16- very helpful–Thanks for posting!

    …also for those that want their colorful emoji’s back to use in outbound email, there is a free add-in that will work. In Outlook go to Home -> Store/Add-ins and search for emoji.

    In Office365[web ver]:
    Option -> Manage ADD-IN
    Click the plus symbol to Add.
    Select Add from Office Store
    Enter Emoji in the Search box

    • Claudia Zarate says:


      Thanks a bunch for showing us how to add the colorful emojis to our regular email. I’m loving them!!
      Have a great day, week and year everyone!!

  17. Matt says:

    Easy fix. Problem is the ‘Segoe UI Emoji Regular’ font is missing from your Win7/8 PC. Find someone with a Windows 10 PC and copy ‘Segoe UI Emoji Regular’ from their PC onto yours. Reboot and your emoji symbols in Office should start working again. 🙂

  18. PG says:

    If using Office Outlook 2016 and get a square box instead of the emoji and using Windows 7 or Windows 8, then this due to a bug (which will be fixed soon), see note:

    • Hi Peter, Yes, that is true, and Robert explains so in his post. I prefer to stick to the What, So What, What’s Next – and leave the Why for more technical blogs.
      Sadly it is June 2017 and many folks still have the issue. Microsoft stated it would be fixed “soon” back in December 2016.

      In all honestly, “just upgrade to Windows 10” will solve the issue too, but that’s not possible for many folks. They missed the deadline to upgrade for free or they’re using legacy LOB apps that require them to live in the past on the legacy OS.

  19. Lindsay says:

    THANK YOU for your solutions! 🙂

  20. Chris says:

    Hmmmm…. In my review pane smiley faces appear, but when I click to view the e-mail it shows a very unfriendly square. This just started to happen recently (it used to work fine). I’ve done all the razzmatazz with the Autocorrect without anything working.

  21. DavidS says:

    Hi Kelly

    I’m on Windows 7 but have just upgraded to Office 365 Outlook 2016, and was having 🙂 mapped to []. I was struggling with various solutions until I found this page:

    and in the post at the end from Peter de Vries on September 12 2017 I found a solution. In brief:

    1. Start a new HTML email but don’t type anything
    2. Click the Insert tab > Symbol > More Symbols …
    3. Select the symbol you want to appear for your smiley
    4. Click the AutoCorrect… button
    5. This enters the symbol into the With: Formatted text field
    6. Type the text for the smiley in the Replace: box, e.g 🙂
    7. Click the Add button

    I checked and the smiley appears correctly in both internal and external emails.

  22. Mats says:

    Download the ttf-files from one of your Windows 10 computers. Install and replace all of them and reboot.


    If you have plenty of time, find out which of the ttf files that contains the missing Emojis 🙂

    • Mats says:

      Sorry, I forgot, the missing fonts are Segoe as in

      i c:\windows\fonts
      Windows 10 has 20 … Windows 7, fewer, replace and you will be happy!

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Kelly Marshall

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