Please process following steps to insert checkbox symbol in Word.

1. Put the cursor at the place you will insert the checkbox symbol, and click Insert > Symbol > More Symbols. See screenshot:

2. In the opening Symbol dialog box, please (1) choose Wingdings 2 from Font draw down list; (2) select one of specified checkbox symbols you will add; (3) click the Insert button. See screenshot:

Now the specified checkbox symbol is inserted at the cursor place.

3. For inserting the specified checkbox symbol at another place, please put the cursor at the place you will insert the symbol, and click the Insert button in the Symbol dialog box.

4. Close the Symbol dialog box.

One click to insert checkbox symbol or checkbox (content control) in Word

In general, you can insert a checkbox symbol with finding it from symbol library, or insert a checkable checkbox control with enabling Developer tab and adding such a content control. Both seem not easy! Do not worry! Kutools for Word provides a Check Box feature, not only supports a various kinds of checkbox symbols, but also can help you insert checkable checkbox control with only one click easily!

This method will guide you to define the specified checkbox symbol as your custom bullets, and then you can easily insert multiple checkbox symbols in bulk by applying the custom bullets. Please do as follows:

1. Select the content you will add the checkbox symbols for, and click Home > Bullets > Define New Bullet. See screenshot:

2. In the opening Define New Bullet dialog box, please click the Symbol button. See screenshot:

3. Now the Symbol dialog box comes out. Please (1) select Windings 2 from the Font drop down list; (2) select one of checkbox symbols from below table; and (3) click the OK button. See screenshot:

4. Click the OK button in the Define New Bullet dialog box.

And now the specified checkbox symbol is added at the font of each row in bulk at once.

Note: If you need to batch add the specified checkbox symbols in future, you can select the rows, and then click the specified checkbox symbol from the Bullets drop down list directly. See screenshot:

If you have Kutools for Word installed, you can apply its Check Box feature to easily insert checkbox symbols with only one click in Word.

Put the cursor at the place you will insert a checkbox symbol, and click Kutools > Check Box, and then specify one of checkbox symbols from the drop down list. See screenshot:

For inserting checkbox symbols at many places, please repeat above processing as you need.

Note: Besides inserting a various kinds of checkbox symbols, Kutools for Word's Check box feature also supports to insert checkbox content controls, checkbox (active X control), and a checkbox list with only one click in Word.