English: He almost could have trapped him again.

My language is VSO so the english is really: trapped almost could have again he him

My language is very morpheme based so there are many kinds of modifiers. The language also has very few words, so the morphemes mix with simple words to create concepts / ideas, much like the verb in the sentence. the Verbum language translation is:

nūnēnesnulnānīnenō jū jūl

Literal translation: [place/thing used as tool for..] [catch things/items](i.e., Trap) [noun used as verb] [past tense] [prospective] [conditional] [iterative] he him.

Honestly, you would most likely not say the english sentence shown, but still the sentence is allowable. So in real life, this conjugation probably would not occur this badly, but I guess I still need to go back and redo some structural design of the language.

So, how about you all? Any similar conjugations that just made you go "Oh crap."

EDIT: Thanks for the examples but part of what I meant was the repetition of the letter N. nū nē nes nul nā nī ne nō