Wormwood's patient has died, and, much to Screwtape's dismay (at losing a soul) and delight (at the pleasure of Wormwood's punishment), the patient is with the Enemy.
Confronted with the reality that Wormwood has not made effective use of cowardice in subverting the Enemy's hold on Wormwood's patient, Screwtape encourages Wormwood to take advantage of fatigue as an assault on the patient's perception of what is "real."
Screwtape confirms that the Germans are going to bomb the area where Wormwood's patient lives and discusses the ramifications of encouraging the patient's cowardice.
Screwtape explains to Wormwood the importance of time in corrupting souls against the Enemy and impresses on Wormwood the counterintuitive need to keep his patient alive through the war.
Finding that Wormwood has allowed his patient to be aware that he is distracted during his prayers, Screwtape instructs Wormwood on how to undermine the patient's belief in answered prayers.
Screwtape advises Wormwood on all the ways that Unselfishness can be used to create bitterness and resentment between Wormwood's patient and the patient's girlfriend.
Screwtape notes that Wormwood's patient's religious experience is "mere" Christianity, and he coaches Wormwood to focus his efforts on subverting the patient's fundamental beliefs by encouraging "Christianity And..." as well as interrupting the patient's balance between change and permanence.
Screwtape sees that Wormwood's patient is vulnerable to developing Spiritual Pride at being accepted into a Christian circle of friends. Screwtape advises Wormwood on how to take advantage of this.
Finding that Wormwood's patient, through the girl he has fallen in love with, is meeting new Christians, Screwtape instructs Wormwood on how to corrupt the patient's spirituality by focusing the patient's interests on the social implications of his religion, especially on the idea of an historical Jesus.
Screwtape castigates Wormwood for letting Wormwood's patient fall in love with a Christian woman. The end of the letter is transcribed by Screwtape's secretary, Toadpipe due to the unfortunate mid-rant transformation of Screwtape into a large centipede.
As Wormwood prepares to use sexual temptation attach his patient's peevishness, Screwtape educates him on using the patient's sense of ownership in his life (especially over how he spends his time) as fruitful soil for creating a sense of injury when his time is taken from him by various demands.
The Enemy has put an end to Wormwood's direct attacks on his patient's chastity, opening the patient's eyes to the damaging truth that attacks on his chastity don't last forever and that he doesn't have to yield to them. Screwtape thus wades into the possibility of using marriage to make the patient unchaste.
After clearing up a bit of misunderstanding about some comments in his previous letter about love that may have sounded heretical, Screwtape continues to counsel Wormwood on whether or not the concept of "love" is good or bad in relation to moving Wormwood's patient away from the enemy.
Screwtape broaches the topic of how to use sexual temptation as a means to corrupt the enemy's "monotonous panacea" called love.
Screwtape notes that his nephew, Wormwood, has overlooked the importance of using gluttony as a means of catching the soul of his patient.
Screwtape admonished Wormwood that he has allowed Wormwood's patient to faithfully attend just one church. Screwtape suggests two additional churches near the patient and summarizes the desirable qualities of each.
Noting a lull in the war (World War II at the time of the writing of this book), Screwtape offers advice to Wormwood about how best to navigate the change in the patient's anxieties, primarily focusing on the outcomes of keeping the patient focused on the Past, Present, or Future.
Hearing that Wormwood's patient is no longer making "confident resolutions" as he was immediately after his conversion (and, hence, experiencing some true humility), Screwtape coaches his nephew how to turn humility to his favor.
Screwtape castigates his nephew, Wormwood, for letting Wormwood's patient experiences two true pleasures, which have resulted in repentance and renewal.
Wormwood's P\patient is slowly drifting away from the zeal of his original Christian conversion, and Screwtape coaches Wormwood not to get into a hurry: to allow the patient's reluctance to be transparent before the Enemy to numb him to both pleasure and pain and take him along gradually away from the Enemy.