The trickiest situation we know of is probably Cortez landing on the mainland of the New World without interpreters.
What occured was that he came across Mayan speakers. Among these he found a Spaniard named Aguilar who alongside a mate had been shipwrecked years before, but been adopted by the local Mayans. Aguilar had a pretty miserable time and was happy to see Cortez and perfectly willing to act as a Mayan-Spanish interpreter.
His mate otoh had got married, had two sons and had effectively "gone native". He even rallied the local natives to attack the Spanish after telling them what their appearance meant for them. They were of course defeated.
It then transpired that Cortez found this Aztec princess, Malinche/Malintzin, sent off to marry some Mayan kingling and possibly resenting the whole situation to the point of wanting some pay-back on her own Aztec kind. She also became Cortez mistress and the mother of his son.
So Cortez would say something in Spanish to Aguilar, who would translate it into Mayan for Malintzin, who would render it into Aztec/Nauhatl.
Those kinds of interactions through many layers of language seem quite common. Stanley in Africa in the late 19th c. would speak Arabic, or possibly Swahili, with his interpreters who would translate into the local lingo. It led to a fair bit of misunderstanding though.