Conditional fields can handle checkboxes in your Templates.
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Below you'll find the steps to create these, and we also cover three options to insert them in your document:

Step 1: Let's say we want to create checkboxes for the client's marital status. First, we create a single-select field with the option of single and married.

Step 2: We build two conditions in the conditional field (each option needs its own field) and in the THEN statement, insert the checked and unchecked box symbols ( ☐, ☒).

Step 3: Duplicate this field and adjust for Married marital status.

Step 4: Insert these fields in the Word document.

Step 1: Create the same single-select field as above

Step 2: Create your conditional field. Your THEN statement will be slightly different, since you're not just automating the checkbox, but you want to list a certain language next to the checkbox:
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Your document's checkbox may have a different shape, and symbols won't work the way you want them. In this case, you can insert text boxes at the top of your checkbox.

Step 1: Follow the same steps, but in the conditional fields, instead of adding these symbols, add an "x".
​Note: in this case, we only add one condition; otherwise, the field should be excluded, and your original checkbox stays blank.
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Step 2: Draw a text box on the top of your checkbox > insert the Woodpecker field > select no fill & no outline for the text box.

Step 3: Follow the same steps with the Married text box.
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Pro Tip: If you need to adjust the placement of the "x", place your cursor over the text box, click, and move the text box. Make sure that your text boxes don't overlap.