Password
Management
by Rick Chin
May 14, 2015
Topics
• Password Problems
• Password Security
• Password Strategies
• Password Managers
Passwords Problems
• Too Simple
• Passwords are Reused
• Too Many Passwords/Sites to Maintain
• Too Complicated
• Sometimes Passwords Expire and Must Be
Changed
Passwords Threats
• You (are too trusting and don’t believe it will happen to you)
• Easier to Guess than Expected
• Brute Force
• Hacking / Keyboard Loggers / Sniffing / Nosy People
• Social Engineering
• Use Familiar “Tricks”
• Transformations and substitutions (f00tb@ll or sdrawkcab)
• Keyboard patterns (qwertyasdf)
• Padding (Montana12&*-&*-&*-)
Password Security
• Passwords need to be mathematically complex
• Passwords are more guessable than you think
• “Complex” is not the same as “Complicated”
• Passwords need to be memorable
Complexity Components
• Length
• Character Set (letters, numbers, symbols)
• Randomness (absence of a discernible pattern)
• Ladnomics (not a word but follows a pattern)
• 8vgz2N'A (no discernable pattern)

8 visa golf zip 2 NUT ' APPLE
Password Length Flaws
• possibilities - 13 characters long
• Readable
• Dictionary word
• Not complex
• iYb48zJ# - 8 characters long
• Short but complex
• Not memorable

Character Set Flaws
• P@ssw0rd
• Multiple character sets
• Easily broken by a computer
Complexity:

human vs. computer
Can You Crack This? (Test 1)
Password: SjdlDijo <— what’s my pattern?
Can You Crack This?
(Answer 1)
• RickChin - shift one character in the alphabet
• A computer will crack this in under 1 second
Can You Crack This? (Test 2)
Password: SkfoHnpw <— what’s my pattern?
Can You Crack This?
(Answer 2)
• RickChin - shift 1x(character position) characters in
the alphabet, character by character
• R =1, shift one to S
• i = 2, shift two to k
• c = 3, shift 3 to f
• etc.
• A computer will crack this quickly
Why Your Passwords

Need Help
• A computer will crack over 2 billion password
combinations in less than 1 second
• If a human could crack 1 password combination
per second continuously (but we can’t), it would
take 3.8 years to crack 2 billion
Password Cracking
• There are many free and commercially available
password crackers and recovery tools
• Rainbow tables and more
• Databases of pre-cracked (i.e., no
computational delay) lists of password
combinations
Ways People Keep Their
Passwords
• Post It Notes
• Taped to the bottom of their keyboard
• Text, Word, or Excel file on their desktop
(password protected or not)
• No place, I use (one, two, three) main
passwords and rotate between them
What Happens When a
Password is Compromised
• Passwords are often entered into a program/database that tries
to access every major bank, credit card company, payment
system, retail stores, email systems, and more at blistering
speed
• They will cross-match with public information records for
addresses and other information to answer security questions
• Information gathered from one system (like email addresses or
mother’s maiden name) will be used in attacks on other systems
• For this reason, reusing passwords is one of the most
dangerous practices you can do
Password Strategy
• There are a few key passwords you must know
• Generally these are passwords you might need often or in an emergency to
get access to everything else. Common examples:
• Master password for a password manager
• Computer login password
• Your Apple ID password
• Dropbox or cloud storage password
• Create strong but memorable passwords for these
• Practice and memorize them
• Use a Password Manager for everything else
Password Managers
• A software vault that stores your passwords
encrypted
• Has a master password that grants access to all the
other passwords
• Can generate and store random complex passwords
that you can use instead of less complex passwords
• Syncs your passwords and makes them available on
the devices you use, wherever you are, even without
Internet access
Suggested Features
• Works in a browser, preferably also on your phone and
tablet
• Autofills most places (occasionally you’ll need to copy
and paste)
• Syncs via Dropbox, iCloud, or their own cloud service
• Preferably syncs automatically, not just when you
manually initiate a sync
• Allows you to share certain logins securely with other
people (like family members)
Example Password
Managers
• 1Password - www.agilebits.com
• LastPass - www.lastpass.com
• Dashlane - www.dashlane.com
• Roboform - www.roboform.com
• iCloud Keychain - availability began in OS X
10.9 and iOS 7

Password Management

  • 1.
  • 2.
    Topics • Password Problems •Password Security • Password Strategies • Password Managers
  • 3.
    Passwords Problems • TooSimple • Passwords are Reused • Too Many Passwords/Sites to Maintain • Too Complicated • Sometimes Passwords Expire and Must Be Changed
  • 4.
    Passwords Threats • You(are too trusting and don’t believe it will happen to you) • Easier to Guess than Expected • Brute Force • Hacking / Keyboard Loggers / Sniffing / Nosy People • Social Engineering • Use Familiar “Tricks” • Transformations and substitutions (f00tb@ll or sdrawkcab) • Keyboard patterns (qwertyasdf) • Padding (Montana12&*-&*-&*-)
  • 5.
    Password Security • Passwordsneed to be mathematically complex • Passwords are more guessable than you think • “Complex” is not the same as “Complicated” • Passwords need to be memorable
  • 6.
    Complexity Components • Length •Character Set (letters, numbers, symbols) • Randomness (absence of a discernible pattern) • Ladnomics (not a word but follows a pattern) • 8vgz2N'A (no discernable pattern)
 8 visa golf zip 2 NUT ' APPLE
  • 7.
    Password Length Flaws •possibilities - 13 characters long • Readable • Dictionary word • Not complex • iYb48zJ# - 8 characters long • Short but complex • Not memorable

  • 8.
    Character Set Flaws •P@ssw0rd • Multiple character sets • Easily broken by a computer
  • 9.
  • 10.
    Can You CrackThis? (Test 1) Password: SjdlDijo <— what’s my pattern?
  • 11.
    Can You CrackThis? (Answer 1) • RickChin - shift one character in the alphabet • A computer will crack this in under 1 second
  • 12.
    Can You CrackThis? (Test 2) Password: SkfoHnpw <— what’s my pattern?
  • 13.
    Can You CrackThis? (Answer 2) • RickChin - shift 1x(character position) characters in the alphabet, character by character • R =1, shift one to S • i = 2, shift two to k • c = 3, shift 3 to f • etc. • A computer will crack this quickly
  • 14.
    Why Your Passwords
 NeedHelp • A computer will crack over 2 billion password combinations in less than 1 second • If a human could crack 1 password combination per second continuously (but we can’t), it would take 3.8 years to crack 2 billion
  • 15.
    Password Cracking • Thereare many free and commercially available password crackers and recovery tools • Rainbow tables and more • Databases of pre-cracked (i.e., no computational delay) lists of password combinations
  • 16.
    Ways People KeepTheir Passwords • Post It Notes • Taped to the bottom of their keyboard • Text, Word, or Excel file on their desktop (password protected or not) • No place, I use (one, two, three) main passwords and rotate between them
  • 17.
    What Happens Whena Password is Compromised • Passwords are often entered into a program/database that tries to access every major bank, credit card company, payment system, retail stores, email systems, and more at blistering speed • They will cross-match with public information records for addresses and other information to answer security questions • Information gathered from one system (like email addresses or mother’s maiden name) will be used in attacks on other systems • For this reason, reusing passwords is one of the most dangerous practices you can do
  • 18.
    Password Strategy • Thereare a few key passwords you must know • Generally these are passwords you might need often or in an emergency to get access to everything else. Common examples: • Master password for a password manager • Computer login password • Your Apple ID password • Dropbox or cloud storage password • Create strong but memorable passwords for these • Practice and memorize them • Use a Password Manager for everything else
  • 19.
    Password Managers • Asoftware vault that stores your passwords encrypted • Has a master password that grants access to all the other passwords • Can generate and store random complex passwords that you can use instead of less complex passwords • Syncs your passwords and makes them available on the devices you use, wherever you are, even without Internet access
  • 20.
    Suggested Features • Worksin a browser, preferably also on your phone and tablet • Autofills most places (occasionally you’ll need to copy and paste) • Syncs via Dropbox, iCloud, or their own cloud service • Preferably syncs automatically, not just when you manually initiate a sync • Allows you to share certain logins securely with other people (like family members)
  • 21.
    Example Password Managers • 1Password- www.agilebits.com • LastPass - www.lastpass.com • Dashlane - www.dashlane.com • Roboform - www.roboform.com • iCloud Keychain - availability began in OS X 10.9 and iOS 7