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I am considering using the DocuSign integration, but I would like to confirm whether it can meet my needs: the PDF HubSpot quote (created for the deal) must be automatically included in the same envelope as the contract that is sent out. Is this possible with the DocuSign API? Has anyone implemented something like this before?

Hi,

Yes a Docusign envelope can contain one or more documents. When creating an envelope via the API, you can attach documents as a Base64 string.

So you can convert the PDF from the third party system to a base64 string and add it to the envelope via the API.

Here is documentation on the concepts of the esign API: https://developers.docusign.com/docs/esign-rest-api/esign101/concepts/

And an example of using the API: https://developers.docusign.com/docs/esign-rest-api/how-to/request-signature-email-remote/