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There is a jump here.

Argument is - it is justified if it benefits the person.

"..would enable Jason to improve his supervisor's opinion of his work." - Now this should benefit the Jason to makes sense. E does that clearly.
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OE for reference:

Overview:
The argument states the principle that withholding information from someone who would find that information painful is not justified if the person would benefit from having the information. The argument then applies this principle to a particular case, concluding that Jane should inform Jason that his supervisor is displeased with his work, even though Jason would find this information painful, since knowing this information would enable Jason to improve his supervisor's opinion of his work. You are asked to identify an assumption that the argument relies on.

The Correct Answer:

E The argument states an exception to the view that it is sometimes justified to withhold painful information; when the information would benefit the recipient, withholding it is never justified. The argument doesn't tell us that Jason would benefit if he were informed of what Jane knows, that his supervisor is displeased with his work; it only tells us that this information would enable Jason to improve his supervisor's opinion of his work. To conclude that Jane should convey what she knows to Jason, we need to fill this gap by assuming that Jason would benefit if he were able to improve his supervisor's opinion of his work.

The Incorrect Answer Choices:

A In order to reach its conclusion, the argument does not need to assume that Jason's situation will worsen if Jane does not tell him that his supervisor is displeased. Jason might benefit from having this information even if his situation would remain unchanged if he were not to receive it, since Jason's supervisor would still be displeased with his work if the situation doesn't change.

B Even if Jason will eventually find out that his supervisor is displeased, it could benefit Jason to find out earlier (by being told by Jane). And the exception to the principle stated in the passage only requires that the person benefit from receiving the information. It does not require that the person would never have the information if it were withheld.

C In order to reach its conclusion, the argument needs to establish that having the information that his supervisor is displeased would benefit Jason. But even if having that information would benefit Jason, he won't necessarily feel grateful for it. He might be unaware of the benefit, or he might simply find the information too painful. So the argument does not need to assume that Jason will be grateful for the information.

D The argument does not need to assume that Jason might eventually improve his supervisor's opinion even if he never learns that his supervisor is displeased. Indeed, if (D) were true, it might indicate that Jason would not benefit from having the information. If that were true, the conclusion would not be supported.
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