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I exemplify with the following, but I ask this in general. How can I learn more about affixes that change meaning, especially those that are 'upended into' their antonyms?

For example, I was researching the etymology of surreptitious:

surreptitious (adj.)
mid-15c., from Latin surrepticius "stolen, furtive, clandestine," from surreptus, past participle of surripere "seize secretly, take away, steal, plagiarize," from assimilated form of sub "from under" (hence, "secretly;" see sub-) + rapere "to snatch" (see rapid).

How did the sub- prefix invert to its antonym sur- (French for 'on')?

Yet (to my surprise), 'subreption {noun}' maintained the sub- prefix.

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    Mostly changes from original forms in borrowings have to do with when and where the word entered the target language, what it sounded like then in the source language, and what the phonology and phonosemantics of the target language was like at that time and place. It's the variable influence of these effects on the original forms that results in variation. And like anything living and emergent, it's only detectable ex post facto.
    – jlawler
    Apr 28, 2015 at 18:08

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This isn't an example of antonymy, but of accidental similarity. The Latin prefix sub- could be assimilated into sur- before an r. This is not the same as French sur 'over', which is from Latin super.

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