Besides the order notes we do not track the sending of emails (POs and OAs/Vouchers) through OPS. If an email recipient is not receiving your emails, most likely they are getting filtered as spam by their email application. If so, most likely the email address that you are sending from is NOT in your recipients contacts and needs to be added so that their gmail (or email app) knows that they are being sent by someone they know.
See this for more information on how your recipients can reclassify your emails as not being spam: https://www.jotform.com/help/404-How-to-Prevent-Emails-from-Landing-in-Gmail-s-Spam-Folder