When you send the user an updated version of a file you've already sent them,
give it a new filename with an incremented version number — report_v2.docx,
report_v3.docx, and so on. If you reuse the filename the user has already
received, the delivery event won't fire and they'll never get the update, even
though the file changed. A filename they haven't seen before is what triggers the
send.
So annotate each iteration with the next version number, and the user receives every version as its own attachment.
Example
report_v1.docx first version sent to the user
report_v2.docx the same file after "make the timeline more detailed"
report_v3.docx after "also add a budget table"