Jason vs Smiley Face – Annoying Outlook Autocorrect Transformation – Solved

This issue is now considered an oldie, but still applicable to some. Have you seen a letter J sneaking in the middle of text here and there into emails you get from various sources? You may have even seen some coming from me!

A friend of mine asked me “Who is J and why is he sending me emails from you?”

At first, I was puzzled, until I came across the same issue described by someone else – I have a habit of placing a smiley face right at the end of my informal emails, and my Outlook converted them into the “truer” smiley face, using the Windings font to make into an emoticon (“Genius” move, Microsoft! ). What happens next depends on what type of email client my recipients use. If it is a Microsoft based email client – more specifically, Outlook – they will see the emoticon – a cute smiley face. But if they do not, their program may go for a different interpretation. For those who do not have Windings as part of their package, smiley may be replaced with the next corresponding character in the “human” font – a letter J. Having them placed at the end of my emails, it looked as if somebody with a name like Jason had initialed my emails. As you can imagine, it presented an issue.

Smiley Face transformes into J
So the battle between Smiley Face and Jason had begun for me.

(Hear me, YouTube Lego Man enthusiasts – a movie idea for you.)

By pure accident I came across this trick: right after seeing โ˜บ pop up in my email, I would hit the BACK key once to watch it transform back into the side smile ๐Ÿ™‚ I’ve been doing it for a while, trying to remember of those who may still be confused by my J; I was unwilling or unable to part with my so Web 2.0 habit of smiling, but growing tired of this repetitive monkey business, I needed a real solution for this Smiley-Face-to-Jย  AutoCorrect problem.

But wait, I thought, this is silly – there is gotta be an app… I mean, bug fix for that! So I Googled the question and viola! tons of advice on this annoying little issue. I’ll spare you the search – here is the answer:

How to change Outlook Characters auto-correct options

IMPORTANT: Open a new message:ย  For some reason folks at Microsoft must’ve thought that just having your Outlook itself open was not enough, so they warn you that Autocorrect options “cannot be changed if there are no documents open”. Anyway… moving along with the solution:

Step 1. File > Info > Options

Change Smiley AutoCorrect in Outlook - Step 1
Change Smiley AutoCorrect in Outlook – Step 1

Step 2. Mail > Spelling and AutoCorrect

Change Smiley AutoCorrect in Outlook - Step 2
Change Smiley AutoCorrect in Outlook – Step 2

Step 3. Proofing > AutoCorrect Options

Change Smiley AutoCorrect in Outlook - Step 3
Change Smiley AutoCorrect in Outlook – Step 3

Step 4. Replace or Delete the emoticon’s AutoCorrect Option

First, find the emoticon you want to replace . Let’s go for a plain smiley :), it being the center of attention here. Use the scroll down barto find the ๐Ÿ™‚

You have 2 options – you can either REPLACE the emoticon with the regular text, or you can REMOVE this option altogether for any specific character.

  • If you want to DELETE it altogether, just select the ๐Ÿ™‚ from the menu, and hit DELETE button.
  • As an option you can REPLACE it with itself – as a plain text. Select Plain text from the options, and type in ๐Ÿ™‚ the corresponding field
Change Smiley AutoCorrect in Outlook - Step 4
Change Smiley AutoCorrect in Outlook – Step 4


I hope it helps you out and saves you time!

As always, if you have any questions or ideas for the computer tips and tricks you want me to cover – let me know.

Truly yours,


…. I mean, D ๐Ÿ™‚


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