@NFREDERICK86 Conditional fields is the best option, which does work with Checkboxes.  Basic setup, add checkbox, expand to the number of checkboxes you need in one checkbox group > set checkbox validation > add other fields that will be triggered by checkbox selection > highlight specific checkbox > select Create Rule for Conditional field (right side properties) > choose the trigger at the top (checkbox checked or unchecked) > hold down CTRL and select fields to trigger (they appear with stripes) > save.  Repeat with next checkbox in the group.  

Here is a DocuSign article to describes the process as well:

https://support.docusign.com/s/document-item?bundleId=gbo1643332197980&topicId=iqw1578456520131.html&_LANG=enus

This is very helpful. Thank you. However, I do not see the Create Rule or Conditional Field. Could it be that I do not have the proper subscription to access this, or is it something that should be available to everyone?

@NFREDERICK86 Conditional Fields is a function that has to be enabled and it very likely is part of certain plans. Have your DocuSign Admin go into Settings > Sending Settings > (checkbox) Enable conditional fields. If the Admin does not see this item to enable then you would need to check with Sales or Support to see if this is part of your DocuSign version purchased.

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