Screwtape Letter #27 – Discussion Guide

Screwtape Letter #27 – Discussion Guide is article #56 in the series: Screwtape Letters. Click button to view titles for entire series

Letter #27

The Screwtape Letters Study Guide

Wormwood seems to be having some difficulties keeping his patient distracted and hiding the truth from him.



My dear Wormwood,

You seem to be doing very little good at present. … Anything, even a sin, which has the total effect of moving him close up to the Enemy, makes against us in the long run.

27.1) Wormwood seems to be having some difficulties keeping his patient distracted and hiding the truth from him.

Below are a few statements that Screwtape has previously made – all relating to something that Wormwood should not allow to happen.

Ch 2: Never let it come to the surface; never let him ask what he expected them to look like.

Ch 3: And, of course, never let him suspect that he has tones and looks which similarly annoy her. As he cannot see or hear himself, this is easily managed.

Ch 4: never let them suspect how much success or failure of that kind depends on whether they are well or ill, fresh or tired, at the moment.

Ch 6: It is your business to see that the patient never thinks of the present fear as his appointed cross, but only of the things he is afraid of.

Ch 17: Never let him notice the medical aspect. Keep him wondering what pride or lack of faith has delivered him into your hands when a simple enquiry into what he has been eating or drinking for the last twenty-four hours would show him whence your ammunition comes and thus enable him by a very little abstinence to imperil your lines of communication.

Ch 24: What you want is to keep a sly self-congratulation mixing with all his thoughts and never allow him to raise the question ‘What, precisely, am I congratulating myself about?’

In this letter, Screwtape says to Wormwood – in that regard –

you have largely failed.

Talk about some reasons that may be behind this failure.



various answers, depending on the person

This is pretty much a review of what you feel are the highlights of the book so far.

In a group setting, it’s good for each person to share so all can see and try to understand the different points of view. We are not all the same, so there’s no reason to expect that everyone would look at this book in the same light.



A promising line is the following. … You will, of course, conceal from him the fact that the prayer for daily bread, interpreted in a ‘spiritual sense’, is really just as crudely petitionary as it is in any other sense.


27.2) Even though Wormwood is failing at hiding the truth – Screwtape continues to send him down this same course of action.

Petitionary is defined as:

the nature of or expressing a petition.

Not too useful. So – what does petition mean, in this sense?

any formal request to a higher authority or deity; entreaty.

Then we get to entreaty, which means:

earnest request or petition; supplication.

Following that thought, we get to what supplication means:

an act or instance of supplicating; humble prayer, entreaty, or petition.

So – getting to the real meaning of what Screwtape has just said here, we see that the patient has a new urgency is his purely humble prayers.

But still – even knowing this – he’s still telling Wormwood to try to hide the truth.

Why is this likely to fail?

And why is Screwtape still pushing this same tactic, in spite of previous failures and knowing that it’s likely to fail again?



Various answers likely

Similar to the previous question- answers will vary.

Maybe the key though – whatever we all come up with – may be the repetition.

In spite of the fact that Screwtape knows Wormwood’s attempts are failing –
he tells Wormwood to continue with the same old attack.

Think about repetition and boredom

Thinking of question 25.2 – about repetition and possible boredom –
I can’t help but wonder if Screwtape pays attention to his own words of advice.

Given the fact that the attempts are failing –
and in fact have led the patient closer to God than ever –
is it really a good idea to try more of the same?
Would they not lead to a feeling that God has already helped to overcome these attacks –
and things are getting better – so why not stick with Him –
or even get more involved?

Revisit the concept of exactly what devils create

Seems like the little devils –
just as they can’t create anything – but only corrupt what already is –
they aren’t too creative in their thinking either.



But since your patient has contracted the terrible habit of obedience, he will probably continue such ‘crude’ prayers whatever you do. … Don’t forget to use the ‘heads I win, tails you lose’ argument. … and thus a granted prayer becomes just as good a proof as a denied one that prayers are ineffective.


27.3) Realizing that Plan A from the previous paragraph probably won’t work – here comes plan B.

Is this more likely to work? Not that’s it’s guaranteed to work – but is it more likely?

Why or why not?




Answers will vary in a (hint:) community

Again – answers may vary as to why it’s likely to fail – especially in the specifics.

One very large problem thought – the patient is in a community that is likely to want to help Him grow at this point. They have been through this themselves – and having come out of it – will be willing and able to help the patient if he so desires. He likely will.



You, being a spirit, will find it difficult to understand how he gets into this confusion. … Why that creative act leaves room for their free will is the problem of problems, the secret behind the Enemy’s nonsense about ‘Love’. … And obviously to watch a man doing something is not to make him do it.


27.4) Let’s define a couple words here – then we can see what Screwtape is saying.

Temporal – enduring for a time only; temporary; transitory ( opposed to eternal).

Corporeal – material; tangible.

What it comes down to then is that people have trouble dealing with the differences between “time” as we see it and “time” as God sees it. No issue there – we do have a problem with that.

He goes on to say the he, Screwtape, understands how people have free will in all of this – but that the problem of problems is why we have it. He only knows that it has something to do with all that nonsense about “Love”.

Do we look at these questions of how and why free will exists in the same way? Or is it different for us?




Again, various possibilities. God loves us too much for all to have all the same answers.

A discussion of free will can cover a lot of territory.

I look at it as essential for us to be able to return God’s love.

Without free will – we’d be nothing more that robots – programmed to love God.
Except that – there’s no love in that!
It’s a pre-programmed action –
the only thing even related to responding is that we responded according to the way we were programmed – not responding to God’s love with love of our own.



It may be replied that some meddlesome human writers, notably Boethius  (Boh-EE-tee-us), have let this secret out. … But thanks be to Our Father and the Historical Point of View, great scholars are now as little nourished by the past as the most ignorant mechanic who holds that ‘history is bunk’,

Your affectionate uncle


27.5) Back to an old topic – reading.

First – some notes on Boethius, from The Society of Archbishop Justus of the Anglican Church.

He was considered to be an educator, a theologian, a statesman, and a philosopher.

In talking about what C S Lewis thought of him, the site says –

If Boethius had been only a statesman and an educator, his name would still be remembered by historians with respect, but only by historians. What makes him immortal is the work written in the last years of his life. C.S. Lewis writes (The Discarded Image, p 75):

“De Consolatione Philosophiae was for centuries the most influential book ever written in Latin. It was translated into Old High German, Italian, Spanish, and Greek; into French by Jean de Meung; into English by Alfred, Chaucer, Elizabeth I, and others. Until about two hundred years ago it would, I think, have been hard to find an educated man in any European country who did not love it.”

In describing what Boethius had to say on the topic of time, all-knowingness, and freedom, they paraphrase it as –

Philosophy has told Boethius that God is all-knowing, that He transcends time, and sees all things and all events, past, present, and future, in one timeless act of awareness. Boethius objects that if God knows today what Jones will do tomorrow, then Jones has no choice in the matter. Providence replies that the nature of knowledge depends not on the thing known but on the knowing faculty. When Jesus knows that Peter will deny Him, He does not observe Peter’s present condition and apply causal principles to extrapolate to Peter’s future act. He sees Peter’s act directly.

Why would Screwtape consider those like Boethius as meddlesome – why would he want people like us to not be studying this book – and then why would he want to cut us off from others who haven’t read it?




Think about why God created us

Because he makes us think.

There’s no cut and dry answer here –
nothing to observe and conclude.

Rather we have to examine ourselves and God.

Keep in mind – God formed us and breathed life into us –

Ge 2:4 This is the account of the heavens and the earth when they were created.

When the LORD God made the earth and the heavens— 5 and no shrub of the field had yet appeared on the earth and no plant of the field had yet sprung up, for the LORD God had not sent rain on the earth and there was no man to work the ground, 6 but streams came up from the earth and watered the whole surface of the ground— 7 the LORD God formed the man from the dust of the ground and breathed into his nostrils the breath of life, and the man became a living being.

If we search to find God in us –
rather that trying to find “us” in us –
that knowledge is in us.

If we don’t even look –
things are much easier for Satan.





Please leave a comment or ask a question - it's nice to hear from you.

Scroll to Top

By continuing to use the site, you agree to the use of cookies. more information

The cookie settings on this website are set to "allow cookies" to give you the best browsing experience possible. If you continue to use this website without changing your cookie settings or you click "Accept" below then you are consenting to this.