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It turns out that Whenever does something weird when you provide a minutes argument that is less than or equal to 30. It assumes you mean 'every n minutes' whereas for values greater than 30, it assumes you mean 'the nth minute'.
Whenever specs describing the behaviour
So, when the random number generates an 8, whenever generates a schedule like this (edited for brevity):
We'll switch to using raw cron syntax instead. From the Readme: