There are two cheating scenarios
1) In person 2) Online
How are these cheating scenarios treated differently in academia?
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Cheating is not a legal concept, fraud is. Obtaining an essay written in India or by your mother is not fraud. Fraud comes in inducing the university to give you something of value (a passing grade, or perhaps admission) based on a material false statement ("I wrote this myself", or making false statements about your interest in tennis). A number of people were recently charged with various forms of fraud (mail fraud and honest services mail fraud) for similar actions (spelled out here). I do not know of any case where a student has been criminally prosecuted for turning in a purchased essay, but in principle it could happen.
Academic fraud does is not punishable by a jail sentence to my knowledge.
The one case where I have never gotten a straight answer is somebody screen sharing homework/tests/quizzes. Technically its social engineering(maybe a jail sentence) but its the same thing people do in real life. One person I know got the police involved but I am not sure what happened.