Si fallo, debería tratar nuevamente.

English Original Sentence

If I should fail, I would try again.

Si fallara trataría nuevamente. [?]

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Either seem correct, but as I understand it the difference is whether the speaker wants to express failure as a likely/possible outcome, vs. an unlikely/impossible outcome. Si fallara would be a situation where failure is unlikely. Since they’re saying they would just try again if they failed, I would say they consider it a likely outcome, hence si fallo.

Doesn’t “If I should” imply a sense of unlikeliness? Mind you, I’m not a native English speaker.

But I think my general unease with this sentence is that it breaks the regular pattern of a hypothetical conditional sentence (past subjunctive … conditional). If the case is likely, it could be a simple as “Si fallo, trato nuevamente”, but that is far from the English original.

I think in a lot of day-to-day situations, saying “If …” indicates that you think the outcome is very possible. For example, “If you think this food is too cold, I can heat it up for you”, “If I’m running late, start the meeting without me”, “If I can’t find the blue shirt, I’ll wear the red one”…etc.

To me, Si fallo, trato de nuevo would be the simplest way to express the idea of the English sentence. Si fallo, debería tratar nuevamente seems like a more fancier/literary/decorated way to express the same idea.