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My book mentions that 1,5-dihydroxypentan-3-one will not give silver mirror with diammine silver(+1):

1,5-dihydroxypentan-3-one

This seems very counter intuitive to me as the alcoholic group can be easily oxidized to the aldehyde which will subsequently give the test.

What is the correct reasoning behind this?

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The molecule as it stands is not an aldehyde. If you turn it into an aldehyde before doing the test, you are not starting with the molecule that is stated to be negative in the test. The chemistry of the Test will not convert your alcohol into an aldehyde and subsequently turn the test positive.

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