Gwendolyn summons Connor, Despereaux, and Bernadette into her office and presents them with an opportunity. After explaining that they show much promise in the Guard, she goes on to ask them if they are willing to deliver some vital parcels to the southern town of Gilpledge, on the outskirts of the wild country. Excited that their training has been noticed, and eager to further impress their Guard leader, the tenderpaws accept, and begin preparations for the long journey.
On the way to Elmoss from Lockhaven, the adventuring mice elect to change their route so that they will be able to stock up and receive guidance in Ivydale. When they arrive, Despereaux visits her senior artisan Apple, a baker, who is able to provide the mice with a special type of bread that provides long sustenance with small consumption. Meanwhile, Connor visits his senior artisan Rana, an expert cartographer. When Connor asks her for her assistance in finding a safer path to Gilpledge, she is able to draw upon past experience to show the crew a safer, shorter route which would take them through a shortcut to Sprucetuck around Elmoss.
Before they reach Sprucetuck, they encounter problematic tall grass and other dangerous hazards such as melting snow and standing water. Faced with these hazards, Bernadette uses her pathfinding abilities to find an alternate route that takes the mice around Sprucetuck and away from the hazards.
Overcome with hunger and exhaustion, and weary from their long journey thus far, the Guard Mice decide to climb and take shelter in a roadside tree. When they arrive at the top, however, they bump straight into a wild raven’s nest. The raveness has a large scar across her left wing. When the raven sees the mice, she instantly covets the mailbag that Connor is wearing around his neck. Desperately trying to maintain their possession of the mailbag with which they were entrusted, the Guard Mice are soon entangled in a heated encounter with the raven. They exchange blows, and although Despereaux frantically leaps at the bird and comes away with one of her eyes, eventually the might of the raven overwhelms the mice and lays them out.
The raven flies away with the mail bag as well as Connor’s shield, although one of the parcels fell out of the bag before her flight. Dazed and exhausted after the encounter, the mice struggle toward the neighboring town of Dorigift to rest and recover from their wounds.