I spoke with 5 different Diamond Desk reps and I'm not happy with the answers I got. None of the reps were from Chisolm or CVG which are the only places I really trust for answers to out of the ordinary questions. In any case, all 5 said no to upgrading with miles. I asked the question, not in general terms but specifically in reference to a FCFL reservation that I have booked.
I have been able to upgrade them for cash, both domestic and international. The only international I did was at the gate for my wife and took a while for the re-issue desk to figure out the fare. In all cases, doing them for cash, change fees were waived (which is pretty standard on a buy up). I didn't ask about "Pay With Miles" since you have to be an AMEX Delta cardholder, Gold, Platinum or Reserve, to do those.

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