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I am experiencing the same thing. I used my Late 2016 as a trade in for the 2019 model and I too am enrolled in the developer program. I have 14 days to turn in my 2016 so i can apply the trade in to my 2019 purchase but I am unable to uprade my 2019 so I can move the 2016 to the 2019 laptop. Very much a pain and I wish I could figure out what the issue is or maybe 10.15 is around the corner? Anyone???