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I would like to provide the option of creating additional text fields under the same Label, if necessary. In the form of an "Add another" button. So when this button is pressed, an additional textfield will appear underneath. So, much like adding unlimited attachments to a node for example.
Is this possible using the Webform module?
The module Webform Add More does similar thing,
Webform Add More enables selected fieldsets to be initially hidden and progressively shown with an Add more button, mimicking CCK multiple fields. The approach was proposed by Bartezz, and code originally implemented by span and kranklin 1. This module adds a checkbox setting to webform fieldset components to select which should have Add more functionality, as well as an advanced setting to override the button label per Webform.
The Select (or other) module provides the functionality similar (or identical?) to what you are looking for. Here is an excerpt about it from its project page.
Provides a new Forms API element which is a select/radios/checkboxes element that has an 'other' option. When 'other' is selected a textfield appears for the user to provide a custom value.
Here is a sample about it:
