SlideShare a Scribd company logo
The Illusion of protection
(commentary on passing encrypted
          data via files)
   Anywhere in US = high profile target
       Large Organizations have a large target profile
         Example: With 50,000 users, SOMEONE is going to
         have the password: *1Passw0rD*
   Access to home machines gives access to work
    most of the time
   Personal AND business information at risk
   Well-funded enemies of the state
     International Criminal Organizations
     State-sponsored enemies
   Hackers with almost unlimited free time
       Anonymous / Lulz Sec
   Logistics for all
       Corporate Resourcing for Hire
         Cloud Services – AWS, Google Cloud, etc.
       Each generation has a knowledgebase upon which to build
         Our children have access to more knowledge than ever before in
          history
       Distribution channels for new attacks
         Internet – fastest distribution methodology history has known
   Generating a random password is harder than it looks
       Randomness does not occur naturally in language
       (English language entropy [sensible language] – 1.5 bits/character)
   Password generation algorithms are patterns
       Pick a word/phrase and mix it up
         n0tY0urP@ssw0rd - Letme!n123 - P@tri0tsRule!!
       Mash the keyboard in a pattern
         1234!@#$qwerQWER - 12qw!@QW
       Password Complexity Rules just limits the usable algorithms
         E.g. cat*town_horse_buddy;itself”computer-
          drapes%query_limits^yuletide@notices
            Strong passwords don’t always meet complexity rules (no caps, no numbers!)
   Rules and patterns severely limit search space
     Hackers don’t have to test millions of passwords that don’t meet the
      complexity criteria
     True randomness doesn’t have rules
     Rules give hackers too much information about the password
   Secure password transmission
       Recommendation #1 – Users should transmit passwords over alternate medium
         Assumption is that if someone can get the document, they can also get the email.
         The level of risk already inherent in the transmission
         Passwords should not be written down, even in emails
       Key changes should be done with all personnel changes (minimum)
   Encoding passwords to be easy to remember
       Train users to get random!
         Five RANDOM common words (tomboy, skateboard, caterpillar, the, mouse)
           Estimated 55 bits of entropy based on a working vocabulary of 2048 words
           Add entropy with personal rules of insertion/capitalization and numbers/symbols
       Compare to ideal AES-128 key = 128 bits of entropy (2^73 x LESS entropy!)
         Compare to AES-256 key = 256 bits of entropy (2^201 x LESS entropy!)
   Technical Controls
       Ensuring adequate salt (randomness) for AES key
         Change salt length to match length of encryption key (32 bytes/256 bits)
       Forced password complexity (? – better than nothing – but good enough - ?)
         Enforcing simple rules can actually REDUCE available entropy
         Improving password complexity rules to force more entropy
   Assigning passwords (give entropy to users)
       Because humans aren’t random – password
        generation should be ‘more’ random
       Password Generation as a Service
   Secure Data Exchange Gateways
       Encrypted IM
       Encrypted email
How encryption is implemented with passphrase-based software

                                                 SECRET INFO
               Passphrase



    Random
    Number                          PBKDF2                            AES-128
   Generator




Salt                                         AES Key                   Encrypted
                                                                         INFO

                        Compress
                        & Package
                          (ZIP)




                                                               Encrypted Doc


           [and that’s a simplified version of the flow-chart]
   Almost everyone in IT knows AES!
       Encryption algorithm
       Current standard (Rijndael)
       Advancement from DES/Triple-DES
   Securing document is not just encryption
       Encryption needs keys
         Keys require handling / (Key Management)
           Key management requires a chains of trust
             Secure generating and trading of random keys is HARD
   Few have heard of PBKDF2
       Used to ‘passphrase’-protected documents
         (pseudo-random keys from simple passphrases)
       Creates AES encryption keys from Passphrases
       One-way algorithm (like a blender)
         Having the output you can’t get the input
       Flexible control
         # of cycles directly related to time to compute results
         Added entropy salted in by user (take the pseudo- out of pseudo-random with
           entropy)
gr@pe_Pudd1ng                                                            SECRET INFO




                                                           random
                                                           AES
                                                           combo

                                   one-way hash
                        101010101010101101011100
                        001010111011011010000111
                        101011010100110101001010
                                                                      AES – pick-proof, complex
                        Salt added to recipe ensures
                        randomness for AES key
                         Email 2




                                                                                                Email 1
Entropy comes from recipe complexity.
A passphrase is created with a recipe that describes it.     Salt and locked safe delivered to recipient
Control of this is possible only with




                                                                                                       Email 2
                                          ONLINE system controls – not
                                          offline documents and files
                                             29 million tries
                                             per hour




                                                                                    ?       If attacker has
                                                                                            access to emails
                                                                                            already, trying
                                                                                            every OTHER
       Attacker has access to Salt so                                                       email in the
       random entropy of AES key does                                                       mailbox will be
       not interfere with trials                                                            quick and easy!

                                            Highly-automated Blender ($329)
                                            29,064,960 recipes/hour
                                            (yes, 29 MILLION!)



The complexity of the recipe and number of potential ingredients is the only thing preventing them from
duplicating the secret formula to recreate the AES key. Note the attacker does not directly brute force AES keys!
With online password systems, we can control speed of attacks with login controls such as timeouts and lockout.
100000   Vocabulary                                             1         100000 100,000 phrases
           1   Capital letter                                         1              1
          32   typewriter symbol                                      1             32
          10   number                                                 1             10
           4   number/cap/sym position                                3             64



               Attacker can choose capital speed/cost                32 GPUs @$250 ea   $            10,528.00
               Attacker capital resources                               Total           $            15,328.00
                                      2,048,000,000                2.20 hours
                                                                   0.09 days

               Amazon GPU Cloud*                     $          81.03                 16 AWS GPU instances
               With cloud computing - attacker no longer worries about capital costs!




               *Amazon GPUs not this fast (yet) -erring on side of caution




Worksheet simulation to examine how password rules/complexity affect attacker cost
Based on attack against MS Word 2010 PBKDF2 algorithm of 100,000 cycles –
Assumption based on using an ATI Radeon HD 5970 – Online price $329
  --- (published attack speed of 20,184 passes/sec with COTS package)

More Related Content

PPTX
Week3 lecture
PDF
Come creare l'esperienza da zero
PPT
ALTOS ESCONDIDOS PANAMA: ECO LUXURY LIVING IN PANAMA
PPTX
Skills development(contents)
PDF
AML Manual AltosEscondidos
PPTX
Physical computing
PDF
The copenhagen protocol oxford
PPTX
Cryptography
Week3 lecture
Come creare l'esperienza da zero
ALTOS ESCONDIDOS PANAMA: ECO LUXURY LIVING IN PANAMA
Skills development(contents)
AML Manual AltosEscondidos
Physical computing
The copenhagen protocol oxford
Cryptography

Similar to Choosing strong passwords (20)

PPT
Introduction To PKI Technology
PPT
6. cryptography
PPTX
Introduction to encryption
PPT
Cryptography
PPTX
Cryptography
PPTX
Encryption And Decryption Using AES Algorithm
PPTX
Cryptography
PPTX
Cryptography
PPTX
EDT 4608 - PART 2 - DATA COMMUNICATION AND COMPUTER NETWORKING
PPTX
Password cracking and brute force
PPTX
Using Cryptography Properly in Applications
PPTX
Intro to modern cryptography
PPT
Computersystemssecurity 090529105555-phpapp01
PPT
Computer Systems Security
PDF
How to Use Cryptography Properly: The Common Mistakes People Make When Using ...
PPTX
Seminar on Encryption and Authenticity
PPTX
Introduction to security_and_crypto
PPTX
Introduction to security_and_crypto
PPTX
Introduction to security_and_crypto
PPTX
Introduction to security_and_crypto
Introduction To PKI Technology
6. cryptography
Introduction to encryption
Cryptography
Cryptography
Encryption And Decryption Using AES Algorithm
Cryptography
Cryptography
EDT 4608 - PART 2 - DATA COMMUNICATION AND COMPUTER NETWORKING
Password cracking and brute force
Using Cryptography Properly in Applications
Intro to modern cryptography
Computersystemssecurity 090529105555-phpapp01
Computer Systems Security
How to Use Cryptography Properly: The Common Mistakes People Make When Using ...
Seminar on Encryption and Authenticity
Introduction to security_and_crypto
Introduction to security_and_crypto
Introduction to security_and_crypto
Introduction to security_and_crypto
Ad

Recently uploaded (20)

PDF
1 - Historical Antecedents, Social Consideration.pdf
PDF
Hybrid model detection and classification of lung cancer
PPTX
TLE Review Electricity (Electricity).pptx
PPTX
The various Industrial Revolutions .pptx
PPTX
Chapter 5: Probability Theory and Statistics
PDF
Developing a website for English-speaking practice to English as a foreign la...
PDF
project resource management chapter-09.pdf
PDF
Getting started with AI Agents and Multi-Agent Systems
PDF
NewMind AI Weekly Chronicles – August ’25 Week III
PDF
Microsoft Solutions Partner Drive Digital Transformation with D365.pdf
PDF
WOOl fibre morphology and structure.pdf for textiles
PDF
How ambidextrous entrepreneurial leaders react to the artificial intelligence...
PDF
Hindi spoken digit analysis for native and non-native speakers
PPTX
observCloud-Native Containerability and monitoring.pptx
PDF
DASA ADMISSION 2024_FirstRound_FirstRank_LastRank.pdf
PDF
Enhancing emotion recognition model for a student engagement use case through...
PPT
Module 1.ppt Iot fundamentals and Architecture
PDF
STKI Israel Market Study 2025 version august
PDF
gpt5_lecture_notes_comprehensive_20250812015547.pdf
PPTX
cloud_computing_Infrastucture_as_cloud_p
1 - Historical Antecedents, Social Consideration.pdf
Hybrid model detection and classification of lung cancer
TLE Review Electricity (Electricity).pptx
The various Industrial Revolutions .pptx
Chapter 5: Probability Theory and Statistics
Developing a website for English-speaking practice to English as a foreign la...
project resource management chapter-09.pdf
Getting started with AI Agents and Multi-Agent Systems
NewMind AI Weekly Chronicles – August ’25 Week III
Microsoft Solutions Partner Drive Digital Transformation with D365.pdf
WOOl fibre morphology and structure.pdf for textiles
How ambidextrous entrepreneurial leaders react to the artificial intelligence...
Hindi spoken digit analysis for native and non-native speakers
observCloud-Native Containerability and monitoring.pptx
DASA ADMISSION 2024_FirstRound_FirstRank_LastRank.pdf
Enhancing emotion recognition model for a student engagement use case through...
Module 1.ppt Iot fundamentals and Architecture
STKI Israel Market Study 2025 version august
gpt5_lecture_notes_comprehensive_20250812015547.pdf
cloud_computing_Infrastucture_as_cloud_p
Ad

Choosing strong passwords

  • 1. The Illusion of protection (commentary on passing encrypted data via files)
  • 2. Anywhere in US = high profile target  Large Organizations have a large target profile  Example: With 50,000 users, SOMEONE is going to have the password: *1Passw0rD*  Access to home machines gives access to work most of the time  Personal AND business information at risk
  • 3. Well-funded enemies of the state  International Criminal Organizations  State-sponsored enemies  Hackers with almost unlimited free time  Anonymous / Lulz Sec  Logistics for all  Corporate Resourcing for Hire  Cloud Services – AWS, Google Cloud, etc.  Each generation has a knowledgebase upon which to build  Our children have access to more knowledge than ever before in history  Distribution channels for new attacks  Internet – fastest distribution methodology history has known
  • 4. Generating a random password is harder than it looks  Randomness does not occur naturally in language  (English language entropy [sensible language] – 1.5 bits/character)  Password generation algorithms are patterns  Pick a word/phrase and mix it up  n0tY0urP@ssw0rd - Letme!n123 - P@tri0tsRule!!  Mash the keyboard in a pattern  1234!@#$qwerQWER - 12qw!@QW  Password Complexity Rules just limits the usable algorithms  E.g. cat*town_horse_buddy;itself”computer- drapes%query_limits^yuletide@notices  Strong passwords don’t always meet complexity rules (no caps, no numbers!)  Rules and patterns severely limit search space  Hackers don’t have to test millions of passwords that don’t meet the complexity criteria  True randomness doesn’t have rules  Rules give hackers too much information about the password
  • 5. Secure password transmission  Recommendation #1 – Users should transmit passwords over alternate medium  Assumption is that if someone can get the document, they can also get the email.  The level of risk already inherent in the transmission  Passwords should not be written down, even in emails  Key changes should be done with all personnel changes (minimum)  Encoding passwords to be easy to remember  Train users to get random!  Five RANDOM common words (tomboy, skateboard, caterpillar, the, mouse)  Estimated 55 bits of entropy based on a working vocabulary of 2048 words  Add entropy with personal rules of insertion/capitalization and numbers/symbols  Compare to ideal AES-128 key = 128 bits of entropy (2^73 x LESS entropy!)  Compare to AES-256 key = 256 bits of entropy (2^201 x LESS entropy!)  Technical Controls  Ensuring adequate salt (randomness) for AES key  Change salt length to match length of encryption key (32 bytes/256 bits)  Forced password complexity (? – better than nothing – but good enough - ?)  Enforcing simple rules can actually REDUCE available entropy  Improving password complexity rules to force more entropy
  • 6. Assigning passwords (give entropy to users)  Because humans aren’t random – password generation should be ‘more’ random  Password Generation as a Service  Secure Data Exchange Gateways  Encrypted IM  Encrypted email
  • 7. How encryption is implemented with passphrase-based software SECRET INFO Passphrase Random Number PBKDF2 AES-128 Generator Salt AES Key Encrypted INFO Compress & Package (ZIP) Encrypted Doc [and that’s a simplified version of the flow-chart]
  • 8. Almost everyone in IT knows AES!  Encryption algorithm  Current standard (Rijndael)  Advancement from DES/Triple-DES  Securing document is not just encryption  Encryption needs keys  Keys require handling / (Key Management)  Key management requires a chains of trust  Secure generating and trading of random keys is HARD  Few have heard of PBKDF2  Used to ‘passphrase’-protected documents  (pseudo-random keys from simple passphrases)  Creates AES encryption keys from Passphrases  One-way algorithm (like a blender)  Having the output you can’t get the input  Flexible control  # of cycles directly related to time to compute results  Added entropy salted in by user (take the pseudo- out of pseudo-random with entropy)
  • 9. gr@pe_Pudd1ng SECRET INFO random AES combo one-way hash 101010101010101101011100 001010111011011010000111 101011010100110101001010 AES – pick-proof, complex Salt added to recipe ensures randomness for AES key Email 2 Email 1 Entropy comes from recipe complexity. A passphrase is created with a recipe that describes it. Salt and locked safe delivered to recipient
  • 10. Control of this is possible only with Email 2 ONLINE system controls – not offline documents and files 29 million tries per hour ? If attacker has access to emails already, trying every OTHER Attacker has access to Salt so email in the random entropy of AES key does mailbox will be not interfere with trials quick and easy! Highly-automated Blender ($329) 29,064,960 recipes/hour (yes, 29 MILLION!) The complexity of the recipe and number of potential ingredients is the only thing preventing them from duplicating the secret formula to recreate the AES key. Note the attacker does not directly brute force AES keys! With online password systems, we can control speed of attacks with login controls such as timeouts and lockout.
  • 11. 100000 Vocabulary 1 100000 100,000 phrases 1 Capital letter 1 1 32 typewriter symbol 1 32 10 number 1 10 4 number/cap/sym position 3 64 Attacker can choose capital speed/cost 32 GPUs @$250 ea $ 10,528.00 Attacker capital resources Total $ 15,328.00 2,048,000,000 2.20 hours 0.09 days Amazon GPU Cloud* $ 81.03 16 AWS GPU instances With cloud computing - attacker no longer worries about capital costs! *Amazon GPUs not this fast (yet) -erring on side of caution Worksheet simulation to examine how password rules/complexity affect attacker cost Based on attack against MS Word 2010 PBKDF2 algorithm of 100,000 cycles – Assumption based on using an ATI Radeon HD 5970 – Online price $329 --- (published attack speed of 20,184 passes/sec with COTS package)