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Attaching rendered documents (pdfs) to email templates

We would like a way to attach a rendered document, like an unofficial transcript or letter, to an email template.

 

Example, we generate a score report (using unofficial transcript layout type), save the PDF, download, then use the email template and upload the same PDF through Populi to send. Ideally, we would attach the 'unrendered' transcript in the template (since it needs the custom data added) and when we go to send the email and select the template, it generates and attaches the PDF dynamically (and I made it a link to be able to open the document in a viewer). 

 
 

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