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In the film Solo: A Star Wars Story, Han Solo appears to already speak and understand Shyriiwook. Where / how did he acquire this ability?
Disney canon will be the accepted answer, but EU answers for public interest won't get a downvote from me (and Disney/Lucasfilm Story Group hasn't shown an aversion to mining EU for backstory details when it suits them).
According to the (canon) prequel novel Star Wars: Most Wanted, Han learned to speak Wookiee from various associates of his gang-leader Lady Proxima.
Han knew a little about Wookiees; he’d encountered some while running errands for Lady Proxima, had even picked up a few words of Shyriiwook. But not enough to be useful. If this fellow didn’t understand Basic, they were screwed.
Note that his ability to understand Shyriiwook is dramatically stronger than his ability to speak it. By the time of the Solo film, he's rather more fluent, suggesting that he had ongoing opportunities to practice this language (and Huttese) for multiple years after the events of the book.
Canon Level: EU
Dewlannamapia (usually referred to as Dewlanna) was a cook aboard the ship Trader's Luck, which was kind of a space going version of Oliver. One of these children was Han Solo, who was about nine at the time.
From the starwars wikia:
Dewlannamapia taught Han to speak and understand the Wookiee language of Shyriiwook.[5] However, it was difficult for Han to reproduce the growls of which Shyriiwook consisted, so he preferred to speak Galactic Basic Standard. As Dewlannamapia understood Basic as well as her own language, the communication between her and Han was fluent. Shrike did not provide his children with education beyond that which was needed in their criminal activities, such as reading and simple math; however, Han's natural desire to defy Shrike led him to pursue further schooling clandestinely. When Dewlannamapia became aware of this, she encouraged Han to study. The young Corellian had a tendency to learn only subjects that he enjoyed and considered useful, like mathematics, and to largely ignore subjects he did not like, particularly history. Dewlannamapia made certain to monitor Han's curriculum, forcing him to learn disciplines that he otherwise would have skipped, and the boy eventually began to like history once he realized that some historical battles were as interesting as the ones he had read about in adventure books.1 Dewlannamapia also taught Han to prepare meals, and he became a fair cook himself. She kept in contact with her son Utchakkaloch, telling him anecdotes about the young Han who loved her wastril bread, and who craved to become a pilot.[6]
All of this is detailed in the first of the Solo books, Paradise Snare written by A.C. Crispin.
