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I have fields in a word document as below:
__Monthly __Quarterly etc.
When I convert to a form the __ field does not populate with a fillable field
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You can always add them manually if Acrobat doesn't automatically add them.
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Did you run the "Prepare Form" or form Wizard?
The PrepareForm works with a very strict format or structure. One usually needs to place the title for the field to the left of the form field. Prepare Form does a very poor job with check boxes and does not create exclusionary groups of check boxes or radio buttons.
I and others prefer to create the form field manually and use the tools within the Prepare From to do this.
If you want the form fields to bee in the source document and the PDF look at using Apache OpenOffice.org Writer or Libre Office Writer. Both products are free and support controls that are forms and export to PDF forms directly from the application.
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This article describe the auto field detection process and how to set it up in Word. It was written for Acrobat 9, but still applies.
https://acrobatusers.com/tutorials/designing-forms-auto-field-detection-adobe-acrobat
Many people prefer to create the fields manually, and you have to do that for any fields that are not created by the auto detection process. Reading this article will give you a good start if you want to use the auto detection.
(If you already have Adobe InDesign, you can create the fields there and export to Interactive PDF.)