2

exert (v.)

1660s, "thrust forth, push out," from Latin exertus/exsertus, past participle of exerere/exserere "thrust out, put forth," from ex "out, from within" (see ex-) + serere "attach, join; arrange, line up" (from PIE root *ser- (2) "to line up").

OED: ... The formation is probably due to antithesis with inserĕre (to insert v.) ...

How did ex- + serere compound to mean the modern meaning above of "thrust forth, push out"? How does it make sense to "attach/join out" something?

2

It doesn't really.

"Insert" (or rather its ancestor in-serere) arose naturally, meaning "to bind into" and later "to insert".

Then, when people wanted an opposite for "insert" (something like "to pull out"), it made sense to swap in- for ex-, its opposite.

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