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When we assign a PO, Contract, COR to a user they will open the attachment, annotate or sign, click Done, then click on their checkmark that they've completed their assignment.
No notifications happens when this occurs so we won't know that it's been done unless we open the attachment or the user has entered a separate comment.
The easiest solution for this I think would be to copy the annotation comments that are tracked on the pdf per user/time into the comments of the record or simply "User A annotated the document" or something so the notification gets triggered.
Perhaps if and when ProjectSight will have an Adobe Sign plugin, it might take care of this issue.
