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Cryptography	in	Python
1
Amirali Sanatinia
amirali@ccs.neu.edu
Northeastern	University
Cryptography
• Cryptography	is	ubiquitous	today
• From	mobile	phones	to	wireless	connections
• Supported	in	almost	every	programming	language
• It	is	even	embedded	in	the	CPUs
• It	is	not	hard	to	do	crypto	right	but	…
2
Crypto	Failures
3
Encryption	Models
4
Encryption
Algorithm
Decryption
Algorithm
Encryption
Key
Decryption
Key
Message
Destination
Plaintext Ciphertext Plaintext
Symmetric encryption:
Asymmetric encryption:
Public key
Shared key Shared key
Private key
Symmetric	vs.	Asymmetric	Encryption
• Symmetric	algorithms	are	much	faster	
– In	the	order	of	a	1000	times	faster
• Symmetric	algorithms	require	a	shared	secret
– Impractical	if	the	communicating	entities	don’t	have	another	secure	
channel
• Both	algorithms	are	combined	to	provide	practical	and	
efficient	secure	communication
– E.g.,	establish	a	secret	session	key	using	asymmetric	crypto	and	use	
symmetric	crypto	for	encrypting	the	traffic
5
Advanced	Encryption	Standard	(AES)
• Also	known	as	Rijndael
• Part	of	NIST	competition
• Requirements
– Fast	in	software	and	hardware
– Block	size:	128;	Key	size:	128,	192	and	256
• Joan	Daemen and	Vincent	Rijmen
• First	published	in	1998
• FIPS	197	on	November	26,	2001
• Other	candidates:	Mars,	RC6,	Serpent,	Twofish
6
Block	Cipher	Mode	of	Operation
• AES	works	on	a	block	of	data	(128	bits)
• To	encrypt	a	large	message,	each	block	needs	
to	be	encrypted
• Different	modes	of	encrypting	the	blocks
– Electronic	Codebook	(ECB)
– Cipher	Block	Chaining	(CBC)
– Counter	(CTR)
7
ECB	vs.	CBC
8
Original ECB CBC
RSA
• One	of	the	first	practical	public	crypto	systems
• Designed	by	Ron	Rivest,	Adi Shamir,	and	
Leonard	Adleman
• First	published	in	1977
• Was	patented	until	September	2000
• Based	on	the	hardness	of	factoring	problem	
and	modular	arithmetic
9
Textbook	RSA
• E(M)	=	Me
mod	n =	C (Encryption)
• D(C)	=	Cd
mod	n =	M (Decryption)
• RSA	parameters	and	basic	(not	secure)	operations:
– p,	q,	two	big	prime	numbers (private,	chosen)
– n =	pq,	f(n)	=	(p-1)(q-1) (public,	calculated)
– e,	with	gcd(f(n),	e)	=	1,		1<e<f(n) (public,	chosen)
– d	=	e-1
mod	f(n) (private,	calculated)
• D(E(M))	=	Med	
mod	n	=	M	kf(n)+1	
=	M (Euler’s	theorem)
10
Example	of	RSA
• Keys	generation:
– p =	5;	q =	11	=>	n =	55
– e =	3	=>	d =	27
• Because	ed =	1	mod	(p-1)(q-1)
– Public	key:	(e,	n);	Private	Key:	(d,	n)
• Encryption
– M =	2
– Encryption(M)	=	Me mod	n =	8
– Decryption(8)	=	8d mod	n =	2	
11
Hashing	Functions
• Input:	long	message
• Output:	short	block	(called	hash or	message	digest)
• Desired	properties:	
– Pre-image:	Given	a	hash	h it	is	computationally	infeasible	to	find	
a	message	m that	produces	h
– Second	preimage:	Given	message	m,	it	is	computationally	
infeasible	to	find	a	message	m’,	(m	≠	m’)	such	that,	h(m)	=	h(m’)
– Collisions:	It	is	computationally	difficult	to	find	any	two	
messages	m,	m’	(m	≠	m’)	such	that,	h(m)	=	h(m’)
• Examples
– Recommended	Hash	Algorithm	(SHA-2,	SHA-3)	by	NIST
– SHA-1:	output	160	bits	being	phased	out
– MD2,	MD4,	and	MD5	by	Ron	Rivest [RFC1319,	1320,	1321]
12
Python	Crypto	Libraries
• PyCrypto
– Oldest	and	most	widely	used
• M2Crypto
– SWIG	binding
• Cryptography*
– PY2,	PY3,	PyPy
– OpenSSL	CFFI	binding
• PyNaCl ,	python-nss,	etc.
13
Cryptography	In	Action
(SHA2)
14
Cryptography	In	Action
(AES	Encryption/Decryption)
15
Cryptography	In	Action
(RSA	Key	Generation)
16
Cryptography	In	Action
(RSA	Encryption/Decryption)
17
Cryptography	In	Action
(Fernet)
18
• Provides	authenticated	encryption
– AES	in	CBC	mode,	128	bit	key,	PKCS7	padding
– SHA256	HMAC	for	authentication
Takeaways
• Don’t	invent	your	own	crypto	algorithm
• Don’t	implement	your	own	crypto	library
• Doing	crypto	in	a	right	way	is	not	difficult
• Use	SSL	for	data	in	transit
• Use	PGP	for	data	at	rest
19
Thank	You!
Questions?
20

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Cryptography in Python