Pgcrypto Avast!

A study in Django's password hashers

Drew Engelson
@handofdoom
tomatohater.com
I’m Drew Engelson.
Intro.

Chief Technologist
Why are we here?
Things I hope to touch on today.
Some background…
YOUR SHOT
national geographic
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national geographic
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national geographic
Single Sign On
national geographic
Architecture
national geographic yourshot

• Python 2.7 • Psycopg2

• Django • Pillow
• Postgres • Celery
• Elasticsearch • Haystack
• RabbitMQ • Gigya
• Memcached • Mapbox
• Akamai
Architecture
national geographic yourshot

Front-End
Google

Application
Analytics
Other NG Vii

Layer
CMS
Services Universe

Membership

Authentica User
Asset Mgmt/UGC API tion Profiles

Membership API
Search Notificatio
Deliver Upload Comments
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Services
Related Geo
Crop & Mapping Ratings Sponsors Social

Layer
Curate Content Location Sharing
Resize APIs

2-way
Badges Metrics
sync Storage

Infrastructure
CDN Taxonomy Following

Layer
SSC MediaGrid
Challenge: Migrate 356k
user logins, invisibly.
Starting points.
Legacy users database.
myshot=# select * from users;
username | password
-------------+------------------------------------
kingdiamond | $1$AEm9NDkI$z9YLtNHjckjz5ZMmsNUrX1
kingbuzzo | $1$Pop9WeOo$2XqJ67vVoIh74Ybk6gSqK1
...
(354,992 rows)

• It’s a Postgres database!

• Password is encrypted.
• Follows a format: $1$______$_____________
Starting out.
Found this Perl script.
#!/usr/bin/perl

...

my $db = “dbi:Pg:dbname=${db_name};host=${db_host}";

...

my $sth = $dbh->prepare("INSERT INTO users (username, password)

VALUES (?, CRYPT(?, GEN_SALT('md5')));");

my $result = $sth->execute($username, $password);

Approach #1.
Crack the passwords.
Approach #1.
Crack the passwords.
• Sweet. This sounds fun!
• How is this done?
• Brute force.
• Identify encryption algorithm.
• Encrypt every possible password with same algorithm.
• Find matches.
575e22bc356137a41abdef379b776dba
What we know about…
575e22bc356137a41abdef379b776dba
• It’s a raw md5, one-way hash.
• To keep it simple today…
• Password length is 4 characters.
• Character set alphanumeric (a-z, A-Z, 0-9).
• 624 = 14,776,336 possible passwords.
Crack password.
Raw md5 hash in Python.
import hashlib, itertools, string, sys, time

hash = sys.argv[1]

# All 14,776,336 4 character passwords (alphanumeric only!)

char_set = string.ascii_letters + string.digits
all_passwords = map(''.join, itertools.product(char_set, repeat=4))

start = time.time()
for attempt in all_passwords:
if ciphertext == hashlib.md5(attempt.encode('utf-8')).hexdigest():
elapsed = (time.time()-start)
print('Cracked in', elapsed, 'seconds. Password is:', attempt)
break
else:
elapsed = (time.time()-start)
print('Can\'t crack password.', elapsed, 'seconds elapsed.')
Crack password.
Cracked md5 hash in Python.
$ python crack.py 575e22bc356137a41abdef379b776dba
Cracked in 5.562524080276489 seconds. Your password is: thor

• Password is thor.
• Cracked in 5.5 seconds.
• Single threaded.
• But…
• Short password.
• Limited character set.
Crack password.
md5 hash with John the Ripper.
• Fast password cracker
• Detects weak Unix passwords
• http://www.openwall.com/john/

$ john --format=Raw-MD5 hash.txt

Loaded 1 password hash (Raw-MD5 [MD5 128/128 SSSE3 20x])
Press 'q' or Ctrl-C to abort, almost any other key for status
thor (?)
1g 0:00:00:03 DONE 3/3 (2017-03-26 16:23) 0.2512g/s 509086p/s 509086c/s
509086C/s than..thio
Use the "--show" option to display all of the cracked passwords reliably
Session completed
Crack password.
Speed considerations.
• 14,776,336 attempts in ~17.9 seconds.
• Or ~0.000001 seconds per attempt.
• This is just 4 character passwords.
• For 8-12 character passwords…
3,279,156,377,874,257,103,616
possibilities.
Crack the password.
Speed considerations.
• Remember, ~0.000001 seconds per attempt,
• Times 3,279,156,377,874,257,103,616 possibilities,
• Equals 3,965,458,719,643,761 seconds.
• That’s 125,743,871 years!
Photo: Adam Selwood (CC)
12 parsecs!
Crack password.
Speeding it up.
• Delegate some computing to a GPU.
• Parallel processing.
• Use a supercomputer.
• Use “the cloud”.
• Cheat.
Rainbow tables.
What are they?
• Precomputed table for reversing cryptographic hash functions,
usually for cracking password hashes.
• RainbowCrack

736ff6a958d6b1c54b897be957323698 thom
88a2a07910827e18acb9a179be5fd798 thon
87cce92f7e96e2795d23e3655ce4c1f0 thoo
36049489e88e3ad83898d13799dae5c6 thop
8527fbb29fa42593243c4f7479be219d thoq
575e22bc356137a41abdef379b776dba thor
71140632a1cdac9f05998b786dd1850d thos
10e03f5f31c2dc5fd5e659e88fd7d087 thot
d39f3967327daee70fac2431efa0d93d thou
a0eb8790c45e7f8470db70332df0c480 thov
e339c57f6f97365e01c6ef59ca33ca6c thow
Rainbow tables.
Defending against rainbow cracks.
• Salt it! hash(password + salt)
• Stretch it! hash(hash(hash(hash(password))))
• Strengthen it! len(password) > 16

# Salt
hashlib.md5((password + salt).encode(‘utf-8')).hexdigest()

# Stretch
for _ in range(10000):
hashed = hashlib.md5(hashed.encode('utf-8')).hexdigest()
What about our passwords?
Can we crack ‘em?
• Password format: $1$______$_________
• $1 indicates the algorithm (md5crypt).
• $______ is the salt.
• $____________ is the hashed password.
• CRYPT(‘password’, GEN_SALT(‘md5’))

These are salted, md5crypt hashes generated

by the pgcrypto extension.
What about our passwords?
Still brute forceable, but slow.
hashes/pgcrypto.txt
$1$AEm9NDkI$z9YLtNHjckjz5ZMmsNUrX1

Let’s crack it with John the Ripper.

$ john —format=md5crypt hashes/pgcrypto.txt

Loaded 1 password hash (md5crypt, crypt(3) $1$ [MD5 128/128 SSSE3 20x])
Press 'q' or Ctrl-C to abort, almost any other key for status
thor (?)
1g 0:00:01:37 DONE 3/3 (2017-03-27 16:38) 0.01024g/s 20766p/s 20766c/s
20766C/s than..thio
Use the "--show" option to display all of the cracked passwords
reliably
Session completed
Approach #2.
Django auth backend.
Django auth backend.
Using the legacy database.
• Django tries auth backend in sequence.
• A custom auth backend requires just 2 methods.
• get_user(user_id)
• authenticate(**credentials)
• Let’s authenticate against the legacy users table.

AUTHENTICATION_BACKENDS = [
'django.contrib.auth.backends.ModelBackend',
'pgcrypto_avast.auth.backends.LegacyAuthBackend',
]
Django auth backend.
Get user.
• Getting the user is simple.
• After a user is authenticated, we need ensure a Django user is
created.

from django.contrib.auth.models import User

class LegacyAuthBackend(object):

def get_user(self, user_id):

try:
return User.objects.get(pk=user_id)
except User.DoesNotExist:
return None
Django auth backend.
Authenticate.
• Expects a username and password.
• Validates against the legacy database using the
pgcrypto.crypt() method.
• Salt is extracted from hashed password.

SELECT 1 FROM legacy_users WHERE username=%s

AND password=CRYPT(%s, password)
Django auth backend.
Authenticate.
class LegacyAuthBackend(object):

def authenticate(self, username=None, password=None):

with connection.cursor() as cursor:
cursor.execute("SELECT 1 FROM legacy_users WHERE username=%s AND \
password=CRYPT(%s, password)",
[username, password])
row = cursor.fetchone()
if row:
try:
user = User.objects.get(username=username)
except User.DoesNotExist:
# Create a new user. Set an unusable password because only the
# legacy_users password is checked.
user = User(username=username)
user.set_unusable_password()
user.save()
return user
return None
Django auth backend.
Demo.
pgcrypto_avast=# \dt
List of relations
Schema | Name | Type | Owner
--------+----------------------------+-------+-----------
...
public | auth_user | table | dengelson
public | legacy_users | table | dengelson
...
(11 rows)

pgcrypto_avast=# SELECT * FROM legacy_users;

username | password
-------------+------------------------------------
kingdiamond | $1$AEm9NDkI$z9YLtNHjckjz5ZMmsNUrX1
kingbuzzo | $1$Pop9WeOo$2XqJ67vVoIh74Ybk6gSqK1
(2 rows)
Approach #3.
Django password hasher.
Password hashers.
How Django stores passwords.
• By default, PBKDF2 algorithm with a SHA256 hash.
• Password stretching - 36,000 iterations. (Django 1.11)
• And a random salt.
Password hashers.
How Django stores passwords.
<algorithm>$<iterations>$<salt>$<hash>
>>> user.password
'pbkdf2_sha256$36000$N41L8srmtbwm$sZzACUVNArYmNGV9ZYdqO7KeCd2VXnpE+MXh7tZzwKg='

Default password hashers

>>> settings.PASSWORD_HASHERS
[
'django.contrib.auth.hashers.PBKDF2PasswordHasher',
'django.contrib.auth.hashers.PBKDF2SHA1PasswordHasher',
'django.contrib.auth.hashers.Argon2PasswordHasher',
'django.contrib.auth.hashers.BCryptSHA256PasswordHasher',
'django.contrib.auth.hashers.BCryptPasswordHasher',
]
Password hasher.
Custom password hasher.
• Subclass django.contrib.auth.hashers.BasePasswordHasher
• When creating your own hasher, you must override…
• algorithm
• verify()
• encode()
• safe_summary()
• Other methods.
• salt()
• must_upgrade()
• harden_runtime()
Password hasher.
Custom password hasher.
class LegacyPasswordHasher(BasePasswordHasher):

algorithm = 'pgcrypto'

def salt(self):
with connection.cursor() as cursor:
cursor.execute("SELECT gen_salt('md5')")
_salt = cursor.fetchall()[0][0]
return _salt

def encode(self, password, salt=None):

assert password
if not salt:
salt = self.salt()
with connection.cursor() as cursor:
cursor.execute("SELECT crypt(%s, %s)", [password, salt])
pghash = cursor.fetchall()[0][0]
return "%s$%s" % (self.algorithm, pghash)
Password hasher.
Custom password hasher.
class LegacyPasswordHasher(BasePasswordHasher):
...
def verify(self, password, encoded):
algorithm, pghash = encoded.split('$', 1)
assert algorithm == self.algorithm
encoded_2 = self.encode(password, pghash)
return constant_time_compare(encoded, encoded_2)

def safe_summary(self, encoded):

algorithm, pghash = encoded.split('$', 1)
assert algorithm == self.algorithm
return OrderedDict([
(_('algorithm'), algorithm),
(_('hash'), mask_hash(pghash)),
])

def harden_runtime(self, password, encoded):

pass
Password hashers.
Demo.
Create a new user, then give custom password hash.

pgcrypto_avast=# UPDATE auth_user

pgcrypto_avast=# SET password=‘pgcrypto$$1$AEm9NDkI$z9YLtNHjckjz5ZMmsNUrX1'
pgcrypto_avast=# WHERE username='kingdiamond';
UPDATE 1
Thank you!
Links and examples

https://github.com/tomatohater/pgcrypto-avast


Slides

http://tomatohater.com

Drew Engelson
@handofdoom
tomatohater.com