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Of the two noun homonyms 'pledge', I'm asking merely about that derived from Latin. For the other homonym from Proto-Germanic , please see this. Etymonline for 'plight (n.1)' :

"condition or state (usually bad)," late 12c., "danger, harm, strife,"
from Anglo-French plit, pleit, Old French pleit, ploit "condition" (13c.), originally "way of folding,"
from Vulgar Latin plictum,
from Latin plicitum, neuter past participle of Latin *plicare "to fold, lay",
from PIE root *plek- "to plait".

Originally in neutral sense (as in modern French en bon plit "in good condition"),
sense of "harmful state" (and current spelling) probably is from convergence and confusion with plight (n.2) via notion of "entangling risk, pledge or promise with great risk to the pledger."

  1. Please see the titled question.

  2. How did a 'way of folding' (which looks limited to folding clothes) generalise to mean '"condition or state (usually bad)'?

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In English, events unfold. In Italian, gli eventi prendono una piega, i.e. they get a fold (usually una brutta piega, a bad one, but that’s how the world goes...) The same thing is referenced by two opposite metaphors. Note that for specific persons or processes we have an almost exact English equivalent: ha preso una brutta piega is a possible traslation of he/she/it took a bad turn.

It is not necessary to posit a convergence of the Germanic and the Romance roots. If vulgar Latin used the same metaphor as present-day Italian, the plic(i)tum, just like its Italian cognate piega, was the fold the events got, and so, by extension, a condition or state. This last step didn’t happen in Italian: we cannot say *È in una brutta piega, but it happened in French (en bon plit is mentioned by your source) and this is enough to explain the English.

However, I’m afraid that the only way your question and my answer can be considered on-topic in this SE is under the title “what can be guessed about late vulgar Latin from Romance etymologies?”. Therefore, I’ve added the vulgar-latin tag to it.

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