[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-. ...
SourceOED (3rd edn, 2017): p 139, Introduction to Logic (2 ed, 2010) by Harry J. Gensler (More at Linguistics)
“Unless” is also equivalent[†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..not”...
1. How did on a less condition (than)
shift to onlesse, and then if not?
2. WhereWhat and howwhere is therethe 'negative connotation'?