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CoreOS has a pretty great update mechanism. You can read about it here: https://coreos.com/using-coreos/updates/

In short, CoreOS maintains two OS partitions, A and B. When an update is available, it is automatically downloaded to the B partition, and upon reboot the B partition becomes active, effectively rotating the partitions.

Droplets running CoreOS will receive automatic updates through the normal CoreOS update service.

I'd seriously worry if I had to rely on Digialocean providing timely OS updates.