The story of Huck and Jim’s adventures on the river in some ways seems nothing but obstacles overcome. After Huck decides (Chapter 8) to help Jim escape, the remaining chapters include numerous variants of their near apprehension. Although Huck had run away, he was presumed dead and he later learns that people think Jim killed him. Although his friends would be glad to see his safe return, he could face consequences for helping a black man flee slavery.

One related obstacle is their nearly getting caught on the island (Chapter 11). Disguised as a girl, Huck conducts a reconnaissance mission on the mainland and thereby learns that the campfire smoke has attracted attention so the men will be looking for Jim. Returning to the island, he warns Jim and they leave on the raft and canoe.

After an eventful trip to Saint Louis, complicated by a storm on the river, they run short of food. Huck overcomes this obstacle by going ashore and stealing food at night. When his curiosity gets the best of him, they go aboard a boat that seems abandoned. The situation grows dire as they realize that not only are there thieves aboard but the gang intends to kill one of its members. When they decide to move away quickly, Huck and Jim discover the raft has broken loose. They overcome this obstacle by hiding out in the thieves’ skiff and getting off the boat, then recovering the raft. After some further complications, they go ashore to sleep.

Back on the river, they face another obstacle: the fog. The current tears the raft loose from where it was tied up, and Jim disappears with it. Huck finally finds him again and tries to cover up his anxiety with a childish trick, but then feels bad about it and is truthful with Jim. In some regards, Huck’s immaturity is the biggest obstacle of all, one that he must constantly remind himself to overcome.

A lot happens between chapter 8 and 16 between Jim and Huck, but the main three obstacles are first that Huck finds out that Jim has escaped from his owner, second the town's folk think that Jim has murdered him, and third, and probably the most important in context to the story, Huck feels guilty about helping an escaped slave.

In chapter 16, Huck ponders about whether he should should turn Jim in. In society's eyes it would be the right thing to do, but Jim is his friend and Huck knows he would feel even worse if he betrayed him.

What's the use you learning to do right, when it's troublesome to do right and ain't no trouble to do wrong, and the wages is just the same. I was stuck. I couldn't answer that.

In the end he decides he is spending too much worrying and he should do whatever comes "handiest" to him at the time.

So I reckoned I wouldn't bother no more about it, but after this always do whichever came handiest at the time.

At the moment the handiest thing is having Jim, a strong older man, by his side.

In Chapter 8, Huck must make the decision of whether of not to help Jim escape. Huck encounters this moral dilemma several times throughout the novel. In fact, the choice between the hypocritical values of society and Huck’s friendship with Jim form the central conflict of the novel.In Chapter 12, we can see the affect the relationship with Jim is having on Huck. As Huck and Jim escape from the steamboat, the Walter Scott, they leave the robbers to die. However, Huck’s conscience begins to bother him, and he decides to find help for them. He finds a watchman on a ferryboat and convinces the watchman that he will get a large reward if he goes checks out the Walter Scott. In Chapter 14, Huck makes the momentous decision to apologize to Jim, a Black man, for playing a cruel joke on Jim and making Jim feel like a fool. But Huck says "I warn't never sorry for it. . ." [the apology]. At this point, Mark Twain stopped writing the book because he had an untenable situation. He had a white boy apologizing to a black man for the first time in American literature. It was three years before Twain started writing the book again, but as you read, you'll notice the novel is much darker and more serious in content as Twain explores the relationship between Jim and Huck and society, itself.