You can check the Delivery Status using the Email and Mail Register views from the Documents list and the Client - Documents tab. Refer to Emails Sent, Received and Draft and Mail Register Views.
When a document has been sent as an attachment, the Activity section in the drawer shows "Marked as Sent" with the date and time and the person who sent it.
Resending an Email or Document
If you need to resend a document by email at any time, you can do so with the Share button (or for practices on the Intermediate plan, the Send button). Refer to Sharing Documents with External Users via Email, OneDrive or myprosperity.
If you need to resend an email, you can do this in the same way as resending a document.