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Comments on How did 'unless' evolve to mean 'if not'?

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How did 'unless' evolve to mean 'if not'?

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[Etymonline:] mid-15c., earlier onlesse, from on lesse (than) "on a less condition (than); see less. The first syllable originally on, but the negative connotation and the lack of stress changed it to un-. ...

OED (3rd edn, 2017):

[A.] 2. Forming a conjunctional phrase introducing a case in which an exception to a preceding (or following) statement will or may exist: except if, if..not.

1. How did on a less condition (than) shift to mean if not?

2. What and where is the 'negative connotation'?

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Is this a duplicate of https://languages.codidact.com/posts/280932/280980#answer-280980 ? (1 comment)
Is this a duplicate of https://languages.codidact.com/posts/280932/280980#answer-280980 ?