Sendmail, set up properly, will log the status of a mail it tried to send. An experienced email admin can read the log and tell you what the status of your file is, whether it was sent, or is waiting to be sent, etc. So could an appropriately written Perl script.

What sendmail cannot do is guarantee the integrity of the file once transmitted. If the receiving server decides to eat the file on the other end, that can't be logged.

That the SMTP protocol doesn't support "guaranteed delivery" is pretty easy to see. The Wikipedia article on SMTP shows a manual SMTP session. And any protocol whose basic outbound steps are:

HELO (or EHLO)
MAIL FROM
RCPT TO
DATA
QUIT

Doesn't have a whole lot of room for, "Oh yeah, I just sent the file you sent me." Understand that SMTP was written in the days of expensive communications, when dialup was common. These servers had to live with imprecise delivery and often longish delays. Servers weren't wired to one another then.

Update: SMTP doesn't guarantee delivery

In reply to Re^2: Create "Sent"-like reference for Sendmail mails. by dwm042
in thread Create "Sent"-like reference for Sendmail mails. by punch_card_don

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