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I'm gonna restart the game, load again and see what happens..
What is interesting though, this time I took out every single enemy soldier, both inside and outside just to make sure. And it worked. Afterwards, I freed all captives, including the captain, sent them all inside the submarine, leaving aside only Tiny and the spy with all three parts of the enigma machine. Once everyone else was inside the sub, I entered the plane with the remaining two characters and the final cutscene played right away.
Now tread carefully and consider my info just a helpful hint. Replaying the entire mission with taking out everyone can easily take you around two or three hours, depending on what strategy you use. I can't say that this is a guarantee, but for me it worked. I'm just glad I was able to obtain that damn achievement and move on. Good luck.