Ok, I'm sorry guys for the trouble. Apparently if I click Send and then leave calibre running, it _does_ go to the Kindle. All this time, I've been doing my management->hitting send->closing calibre too soon.
This became evident when I sent the emails to my other email accounts, I'd leave calibre running while waiting for a mail.
/facepalm on self
Thanks guys.
Mods you can close this thread as the problem is solved. (Error code: PEBKAC)
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