@willgproctor I have not run into any such situation but I had a few items I thought were relevant.
- Any unusual FONT style that might be used in the PDF?
- Is the PDF being created and saved with Adobe Acrobat product or other application?
- Any attempts to optimize or compress layers in the PDF?
I can only suggest a few items:
- Try exporting to Postscript file then create a new PDF from that PS file.
- Try taking the PDF and printing the base PDF through Print to PDF File and see if the new file that is saved in the process reacts differently to being added to a DocuSign envelope or Template.