Exercise 1.1 from Introduction to Modern Cryptography, 2nd Edition:

Decrypt the ciphertext provided at the end of the section on mono-alphabetic substitution ciphers.



The mono-alphabetic substitution cipher maps a plaintext, whose elements are from a set of of symbols to a ciphertext, whose elements are also from a set of symbols. Assuming our plaintext can contain the 26 lowercase characters in the English language, and the ciphertext the 26 uppercase characters, encryption can be implemented using the tr command as follows:

tr abcdefghijklmnopqrstuvwxyz $KEY < plaintext

and decryption:

tr $KEY abcdefghijklmnopqrstuvwxyz < ciphertext

where $KEY 26 character key that is a permuation of the 26 uppercase English characters (e.g., ABCDEFGHIJKLMNOPQRSTUVWXYZ, BXZDEQGHIJKLMNOFRSVCYWTUPA, etc).

There are possible keys. However, the text describes an attack on the cipher that makes use of the known frequency of characters in the English language to narrow the key to a smaller number of probable keys. It then goes on to say:

It should not be surprising that the mono-alphabetic substitution cipher can be quickly broken, since puzzles based on this cipher appear in newspapers (and are solved by some people before their morning coffee!). We recommend that you try to decipher the following ciphertext—this should convince you how easy the attack is to carry out.

Unfortunately, I was not able to solve it before my morning coffee. Nor next morning’s coffee. Or the next… well you get the picture. It was harder than the text made it seems. Especially since I didn’t…

Read the Errata

The text provides an incorrect table of English letter frequencies. I discovered this after a few days of working on the problem (ahhhhhhhh!). The issue is documented in the errata. I have a corrected frequency table on github.

The Attack

Once I had the correct English language frequency table, I also made use of the tools I developed for the problem and also a list of 2 character frequencies to help me narrow in on the key.

Step 1 Produce a frequency table of the ciphertext characters, sorted by count. Put this next to the english text frequency table sorted by frequency:

e   12.7    F   37
t   9.1 Q   26
a   8.2 W   21
o   7.5 G   19
i   7.0 L   17
n   6.7 O   16
s   6.3 V   15
h   6.1 H   14
r   6.0 B   12
d   4.3 P   10
l   4.0 J   9
u   2.8 I   9
c   2.8 Z   7
w   2.4 R   7
m   2.4 M   4
f   2.2 E   4
y   2.0 Y   3
g   2.0 K   3
p   1.9 C   3
b   1.5 A   3
v   1.0 S   2
k   0.8 D   2
x   0.2 X   1
j   0.2
z   0.1
q   0.1

Some of the characters (j, z, and q) don’t have corresponding ciphertext entries. That indicates the plaintext that generated the ciphertext was also missing 3 letters (the most probable missing letters being j, z, and q).

Step 2 Build a probable key by sorting the table from step 1 by english plaintext letter, and then by selecting columns 1 (the plaintext column) and column 3 (the ciphertext column). This can also be produced using most_probable_key.sh:

./most_probable_key.sh < ciphertext

Where the 3 ?s stand for the 3 characters that don’t appear in the ciphertext.

Step 3: Ciphertext Decrypt 1 Decrypt the ciphertext with the most probable key generated in the previous step.

tr 'WAZPFEKHL?DJMOGC?BVQISRXY?' abcdefghijklmnopqrstuvwxyz < ciphertext    

If you’re some sort of savant, perhaps you can pattern recognize that in your head, but I got nowhere with it.

Step 4: Digraph Frequencies According to this digraph frequency table, the 10 most common digraphs in English are:

Digraph Frequency
th 1.52
he 1.28
in 0.94
er 0.94
an 0.82
re 0.68
nd 0.63
at 0.59
on 0.57

Using the pattern_frequency.go tool, I built a table of the top 10 ciphertext digraphs:

tr -d '\n' < ciphertext | \
	go run pattern_frequency.go -length 2 | \
	sort -k2 -nr | head -n 10
QV	9
FP	8
VF	7
GF	7
QO	6
PF	5
OL	5
FW	5
FG	5
WQ	4

At this point, I started at the top of both tables and then filled out the rest. For example, implies .

Iteration 1, assume :

Plaintext Frequency Ciphertext
th 1.52 QV
he 1.28 V?
in 0.94 ??
er 0.94 ??
an 0.82 ??
re 0.68 ??
nd 0.63 ??
at 0.59 ?V
on 0.57 ??

Iteration 2, assume . This wasn’t a guess; the probable key generator suggested this relationship.

Plaintext Frequency Ciphertext
th 1.52 QV
he 1.28 VF
in 0.94 ??
er 0.94 F?
an 0.82 ??
re 0.68 ?F
nd 0.63 ??
at 0.59 ?V
on 0.57 ??

Iteration 3, assume . I choose this because I need er and re and have PF and FP:

Plaintext Frequency Ciphertext
th 1.52 QV
he 1.28 VF
in 0.94 ??
er 0.94 FP
an 0.82 ??
re 0.68 PF
nd 0.63 ??
at 0.59 ?V
on 0.57 ??

Iteration 5, one digraph on my ciphertext list is QO. I’ve already assumed the , and the most common English digraph on the full table (not the top 10 I’m using here) shows the most second most common digraph beginning with a t (after th) is to, so I’ll make .

Plaintext Frequency Ciphertext
th 1.52 QV
he 1.28 VF
in 0.94 ??
er 0.94 FP
an 0.82 ??
re 0.68 PF
nd 0.63 ??
at 0.59 ?V
on 0.57 O?
to 0.52 QO

Step 5: Decrypt 2. Try decrypting with the probable key, modified with the digraph analysis:

tr 'WAZBFEKVL?DJMGOC?PHQISRXY?' abcdefghijklmnopqrstuvwxyz < ciphertext

the appear 4 times. Might be on the right track.

Step 6: Iterate on longer words. Use pattern_frequency.go to look for patterns in ciphertext that appear multiple times. This process is automated for patterns 2–10 characters in length in analyze.sh. Iterating on this output is a bit easier than the raw ciphertext, because its easier to see separation between words:

First try:

./analyze.sh ciphertext| tr 'WAZBFEKVL?DJMGOC?PHQISRXY?' abcdefghijklmnopqrstuvwxyz
at	4
en	5
ea	5
oi	5
re	5
to	6
ne	7
he	7
er	8
th	9
hst	2
asn	2
ath	2
lhe	3
top	3
ths	3
alh	3
ere	4
the	4
her	4
nwmt	2
lnwm	2
othe	2
thst	2

thst is probably that, so swap a and s in the key. oi isn’t common, and we’re already pretty sure about o being in the right place, and on is high on the frequency list so switch i and n.

./analyze.sh ciphertext| tr 'HAZBFEKVG?DJMLOC?PWQISRXY?' abcdefghijklmnopqrstuvwxyz
st	4
ei	5
es	5
on	5
re	5
to	6
ie	7
he	7
er	8
th	9
hat	2
sai	2
sth	2
lhe	3
top	3
tha	3
slh	3
ere	4
the	4
her	4

Decrypt 3.

tr 'HAZBFEKVG?DJMLOC?PWQISRXY?' abcdefghijklmnopqrstuvwxyz < ciphertext

Not sure if this is forward or backward progress, but I now notice a couple things that look like words: unfoitunate and ieason. Both would benefit from swapping r and i.

tr 'HAZBFEKVP?DJMLOC?GWQISRXY?' abcdefghijklmnopqrstuvwxyz < ciphertext

Breaking up by eyeball and we can see lots of words now.

lrwmtoyramhdlswsteisareektreiecwgdffdlucttopudcgneberthecess for
soie reason ianwnonekmertsdnsdstongesdyndnyn even lrwmtdonslhei
es that seei to the itopeioreselure than anwother slheie on earth the unf
ortunate truth hoveberds that sulhslheies are usuaccwtrdbdactopreax

for soie reason is probably for some reason, so swap i and m. are usuaccw could be are usually so try swapping c for l and w for y.

tr 'HAJBFEKVM?DZPLOC?GWQISYXR?' abcdefghijklmnopqrstuvwxyz < ciphertext

Breaking up again:

cryitowraihdc systems are ektremely gdffdcult to pudlgneber theless for
some reason many none kiertsdnsdstongesdwndnwn even cry it don schemes
that seem to them to pe more secure than any other scheme on earth the
unfortunate truth hoveberds that such schemes are usually trdbdaltopreax

ektremely gdffdcult looks like extremely difficult, so swap k for x, d for g, and i for d. to pe more looks like to be more, so swap p for b.

tr 'HCJKFEMVB?XZPLOA?GWQISYDR?' abcdefghijklmnopqrstuvwxyz < ciphertext

Breaking it up:

crygtowraghic systems are extremely difficult to build nepertheless for
some reason many non exgerts insist on desiwninwnev encrygtion schemes
that seem to them to be more secure than any other scheme on earth the
unfortunate truth hoveper is that such schemes are usually tripial to break

OK, almost done now. nepertheless is nevertheless, so swap p for v. crygtowraghic is cryptographic, so swap g for p and w for g.

tr 'HCJKFEYVB?XZPLOM?GWQIASDR?' abcdefghijklmnopqrstuvwxyz < ciphertext

Broken up:

cryptographic systems are extremely difficult to build nevertheless
for some reason many non experts insist on designing new encryption
schemes that seem to them to be more secure than any other scheme on earth
the unfortunate truth however is that such schemes are usually trivial to break