Once Tim has decided that he wants to run Mr. Heron's errand, he waits for an excuse to see Mr. Heron. Within two days, this excuse comes when Mr. Heron orders a keg of rum from the tavern and Father sends Tim to deliver it. At the delivery, Tim volunteers to run the errand. Mr. Heron asks Tim to set out with a letter the following morning. The next morning, Tim tells his father that he will be fishing all day. He goes to see Mr. Heron, who explains that he must deliver a letter to Fairfield, which is a five-hour walk away. While walking, Tim runs into Betsy, who spies the letter and begins to tease Tim about it being a love letter. Tim lies and says he is going fishing, thinking that he hates lying and lying is a sin. Betsy tells Tim that she is going to visit Sam. Tim is shocked to hear this. Betsy evades his questions about Sam's whereabouts and experiences, declaring smugly that Tim is a Tory and therefore doesn't deserve to know. Tim does make her tell him that the source of her information about Sam was Mr. Heron, and Tim wonders aloud why Mr. Heron said nothing to him about Sam that morning.
Betsy immediately deduces that Tim is carrying a letter for Mr. Heron, and she demands to have it, fearful that it is a spy report that would endanger Sam. Tim refuses to believe her or give her the letter, fearing he may get thrown in jail for opening the letter to check. Betsy counters that Sam may get killed if he does not open the letter. She lunges for him and the two fight bitterly, hitting each other. Betsy wins the fight, snatching up the letter and running. She reads it and discards it on the road. Tim follows her and picks up the slip of paper, which reads, "If this message is received, then we will know that the messenger is reliable."
Throughout the summer of 1776, Tim manages to avoid Mr. Heron after failing to deliver his letter. Soon Tim forgets about the whole thing. Food is still short, but the Meekers are not in dire straits. They receive two letters from Sam speaking of high spirits but bad living conditions. Mother and Father argue about whether to respond to him or not. Father says Sam should not be given the impression that they approve of his betrayal. When the second letter arrives, Mother points out the irony that Father hates people telling him what to do, yet he insists that Sam respect his authority. Mother decides to write, regardless of Father's disapproval. November nears, and Father needs to make his annual trip to Verplancks Point to sell cattle and stock up on supplies for the tavern. He consult almanacs, trying to time his trip close enough to winter that the buyers are desperate for cattle, but not so close that snow will plague the journey. Usually Sam makes the trip with Father, but this year Father takes Tim, even though he considers him too young for such a long and difficult trip.
As they set out, Tim enjoys the young children watching him. He is proud to be doing an adult task. Father and Tim are stopped in Ridgebury by six "cow-boys," armed cattle thieves. The cow-boys ask Father where he is going with his cattle and then remind him that Verplancks is in British-occupied New York, and his beef will go to feed the enemy army. They speak roughly to Father, calling him "Tory" and demanding that he get off his horse. The cow-boys then send Tim away to a field while they beat Father on the head with their pistols. Just as Tim cries out to them not to shoot his father, several Loyalist horsemen arrive on the scene and scare the cow-boys away, then escorting Tim and his father to their relatives' house in New Salem.
When Tim tries to deliver the letter for Mr. Huron, we see his fundamental innocence. He is a bad liar and therefore a useless messenger in wartime. He cannot help blushing when asked questions that he does not want to answer, and he belies his thoughts and sentiments, musing aloud about why Mr. Heron did not tell him about Sam's arrival at home. Betsy, quick and suspicious, catches Tim, and the entire trip fails. Before the war began, Tim never had occasion to develop sneakiness. Betsy, on the other hand, has grown up in a patriotic, war- involved family, and she instinctively understands and distrusts spies and messengers. Betsy's war expertise has perhaps saved Tim from a dangerous obligation to Mr. Heron, although we can never know for sure how Tim's job would have evolved had he succeeded in delivering the test message to Fairfield.
It is intense loyalty to Sam that lands Sam's brother and Sam's girlfriend in a nasty physical fight with each other. Tim's desperation to impress Sam is countered and ultimately defeated by Betsy's desperation to keep Sam safe from what might have been a spy message. Their fight indicates only a shared adoration of Sam. This scene reinstates the extent to which Sam is a driving force in the lives of the people who know him, admire him, and love him. It also gestures at his carelessness, for he does not seem to notice what other people go through in order to dazzle and protect him. The message sequence also reveals the strangeness of Mr. Heron's character. Mr. Heron is a real person who was thought to be a double agent in the Revolutionary War, but nobody is certain of his role. In this novel, he is another example of the muddled state of the two sides, suggesting that nobody can be entirely trusted, and the sides are not clearly defined or separated.