I’m titillated when one word can carry meanings that are opposite to each other.
One of those words is oversight. It can mean careful supervision, but also careless error.
To be engaged in oversight is enigmatic.
Words like this remind us of how important it is to ensure redundancy in our communication so that messages may be received without incurring bewilderment.
One contronym I haven't thought to address more is 'transparent'. And I use that word a lot. I of course use in the sense of making something obvious, and being honest about functionality and inner workings when it comes to digital services.
Many tech companies do apply transparency for the data that would hold them accountable, but in the word's reverse meaning: making invisible.