This method will guide you to configure the AutoCorrect settings to automatically replace specified text with a winking smiley face or animated emotion, and then easily insert winking/animated smiley faces by tying the specified text in Outlook easily.

Note: Before below steps, you have to save the pictures of winking smiley faces or animated gif images on your hard discs. If you haven’t, you can save below pictures as yours:

                                     

1. In the Mail view, click Home > New Email to create a new email.

2. In the new Message window, please click Insert > Pictures. See screenshot:

3. In the Insert Picture dialog box, please (1) click to open the specified folder you save the pictures of winking smiley faces or animated emotions in, (2) select these pictures, and then (3) click the Insert button. See screenshot:

4. Now these picture or gif images are inserted in your email. Please select one of them, and click File > Options.

5. In the Outlook Options dialog box, click Mail in the left bar, and then click the Spelling and Autocorrect button in the Compose messages section. See screenshot:

6. In the Editor Options dialog box, click Proofing in the left bar, and then click the AutoCorrect Options button in the AutoCorrect options section. See screenshot:

7. Now you get into the AutoCorrect in Email dialog box, please do as below screenshot shown:
(1) Click the AutoCorrect tab;
(2) In the Replace box, type the specified text which will be replaced with the selected picture or gif image;
(3) Check the Formatted text option;
(4) Click the Add button.

8. Click the OK button successively to close all dialog boxes.

9. For adding other winking smiley faces or animated emotions, please repeat above Step 4-8.

From now on, when you type the specified text and press the Enter key in emails, the specified text will be replaced with the selected picture or gif image automatically. See screenshot:

Note: This method cannot insert winking smiley faces or animated emotions into subjects. Please click here for solution of inserting smiley faces in subject.

If you have Kutools for Outlook installed, you can save all inserted winking smiley faces or animated emotions as AutoText entries with the AutoText feature, and then reusing them easily in future with only one click.

1. In the Mail view, click Home > New Email to create a new email, and then click Insert > Pictures in the new Message window. See screenshot:

2. In the opening Insert Picture dialog box, please (1) open the folder containing winking smiley faces or animated emotions, (2) select them, and (3) click the Insert button. See screenshot:

And now the winking smiley faces or animated emotions are inserted into the new email.

3. (1) Select one of winking smiley faces or animated emotions, (2) click the Add button  in the Auto Text pane, (3) type a name for the new entry in the Auto Text dialog box, and finally (4) click the OK button. See screenshot:

Notes:
(1) The Auto Text pane is provides by Kutools for Outlook, and it’s enabled in message window by default. If the pane is invisible, please click Kutools > Pane to enable it.

(2) This step will add one picture as AutoText entry. For adding more winking smiley faces or animated emotions, please repeat this step to add one by one.

Now the winking smiley faces or animated emotions are saved as AutoText entries, you can easily insert them with clicking the Insert button  behind them.

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