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I think I found the answer, if you select stuff like extra storage blocks, the configuration Digital Ocean performs on the droplet ignores the cloudinit. Possible bug?
Why do I think this? I ran a new droplet creation without block storage / volume creation, and the cloud init worked heavenly!
Hello friend!
I was not able to replicate this by adding a storage volume. It may be worth opening a support ticket and letting our support team know all of the variables in play for this so that we can run through a similar scenario :)
Kind Regards, Jarland