1. Public Key Infrastructure – tell me in plain English AND THEN deep technical how PKI works
Steve Lamb
IT Pro Security Evangelist
Microsoft Ltd

2. Objectives Demystify commonly used terminology Explain how PKI works
Get you playing with PKI in the lab
Make some simple recommendations

3. Agenda Foundational Concept (level 200) PKI and Signatures (level 330)
Recommendations (level 310)
Reference material
Common Algorithms (level 360)

4. What can PKI enable? Secure Email – sign and/or encrypt messages
Secure browsing – SSL – authentication and encryption
Secure code – authenticode
Secure wireless – PEAP & EAP-TLS
Secure documents – Rights Management
Secure networks – segmentation via IPsec
Secure files – Encrypted File System(EFS)

5. Foundational Concepts

6. Encryption vs. Authentication
Encrypted information cannot be automatically trusted
You still need authentication
Which we can implement using encryption, of course

7. Assets What we are securing? This session is not about securing:
Data
Services (i.e. business etc. applications or their individually accessible parts)
This session is not about securing:
People (sorry), cables, carpets, typewriters and computers (!?)
Some assets are key assets
Passwords, private keys etc…

8. Digital Security as Extension of Physical Security of Key Assets
Strong Physical Security of KA
Strong Digital Security
Good Security Everywhere
Weak Physical Security of KA
Strong Digital Security
Insecure Environment
Strong Physical Security of KA
Weak Digital Security
Insecure Environment

9. Remember CP and CPS!
“The Certification Practice & Certification Practice Statement (CP/CPS) is a formal statement that describes who may have certificates, how certificates are generated and what they may be used for.”

10. Symmetric Key Cryptography
Plain-text input
Cipher-text
Plain-text output
“The quick brown fox jumps over the lazy dog”
“The quick brown fox jumps over the lazy dog”
Encryption
Decryption
Same key (shared secret)

11. Symmetric Pros and Cons
Strength:
Simple and really very fast (order of 1000 to faster than asymmetric mechanisms)
Super-fast (and somewhat more secure) if done in hardware (DES, Rijndael)
Weakness:
Must agree the key beforehand
Securely pass the key to the other party

12. Public Key Cryptography
Knowledge of the encryption key doesn’t give you knowledge of the decryption key
Receiver of information generates a pair of keys
Publish the public key in a directory
Then anyone can send him messages that only she can read

13. Public Key Encryption Recipient’s private key Recipient’s public key
Clear-text Input
Cipher-text
Clear-text Output
“The quick brown fox jumps over the lazy dog”
“The quick brown fox jumps over the lazy dog”
Encryption
Decryption
public
private
Different keys
Recipient’s public key
Recipient’s private key

14. Public Key Pros and Cons
Weakness:
Extremely slow
Susceptible to “known ciphertext” attack
Problem of trusting public key (see later on PKI)
Strength
Solves problem of passing the key
Allows establishment of trust context between parties

15. Hybrid Encryption (Real World)
Launch key
for nuclear
missile
“RedHeat”
is...
RNG
Randomly-
Generated symmetric “session” key
Symmetric encryption
(e.g. DES)
*#$fjda^j
u539!3t
t389E
5e%32\^kd
Symmetric key encrypted asymmetrically (e.g., RSA)
Digital Envelope
User’s
public key
(in certificate)
As above, repeated for other recipients or recovery agents
Digital Envelope
Other recipient’s or agent’s public key (in certificate)
in recovery policy

16. Hybrid Decryption
*#$fjda^j
u539!3t
t389E
5e%32\^kd
Launch key
for nuclear
missile
“RedHeat”
is...
Symmetric decryption (e.g. DES)
Digital Envelope
Asymmetric decryption of “session” key (e.g. RSA)
Symmetric “session” key
Session key must be decrypted using the recipient’s private key
Digital envelope contains “session” key encrypted using recipient’s public key
Recipient’s private key

17. PKI and Signatures

18. Public Key Distribution Problem
We just solved the problem of symmetric key distribution by using public/private keys
But…
Scott creates a keypair (private/public) and quickly tells the world that the public key he published belongs to Bill
People send confidential stuff to Bill
Bill does not have the private key to read them…
Scott reads Bill’s messages 

19. Eureka!
We need PKI to solve that problem
And a few others…

20. Creating a Digital Signature
Message or File
128 bits Message Digest
Digital Signature
This is a really long message about Bill’s…
Hash Function (SHA, MD5)
Asymmetric Encryption
private
Calculate a short message digest from even a long input using a one-way message digest function (hash)
Signatory’s private key

21. Verifying a Digital Signature
Jrf843kjf gf*£$&Hd if*7oUsd FHSD(**
Py75c%bn&*) 9|fDe^bDFaq &nmdFg$5kn vMd’rkvegMs”
Asymmetric decryption (e.g. RSA)
Everyone has access to trusted public key of the signatory
Signatory’s public key
Digital Signature
? == ?
Are They Same?
This is a really long message about Bill’s…
Same hash function (e.g. MD5, SHA…)
Original Message
Py75c%bn&*) 9|fDe^bDFaq &nmdFg$5kn vMd’rkvegMs”

22. Word About Smartcards
Some smartcards are “dumb”, i.e. they are only a memory chip
Not recommended for storing a private key used in a challenge test (verifying identity)
Anyway, they are still better than leaving keys on a floppy disk or on the hard drive
Cryptographically-enabled smartcards are more expensive but they give much more security
Private key is secure and used as needed
Additional protection (password, biometrics) is possible
Hardware implements some algorithms
Self-destruct is possible

23. Recommendations Don’t be scared of PKI!
Set up a test environment to enable hyou to “play”
Minimise the scope of your first implementation
Read up on CP & CPS
Document the purpose and operating procedures of your PKI

24. Summary Cryptography is a rich and amazingly mature field
We all rely on it, everyday, with our lives
Know the basics and make good choices avoiding common pitfalls
Plan your PKI early
Avoid very new and unknown solutions
Certificate Policy
Certification Practises statement

25. References Visit www.microsoft.com/security
Read sci.crypt (incl. archives)
Attend SEC499 for “Encryption in Detail” on Friday at in Room 1
For more detail, read:
Cryptography: An Introduction, N. Smart, McGraw-Hill, ISBN
Practical Cryptography, N. Ferguson & B. Schneier, Wiley, ISBN
Contemporary Cryptography, R. Oppliger, Artech House, ISBN (to be published May 2005, see
Applied Cryptography, B. Schneier, John Wiley & Sons, ISBN
Handbook of Applied Cryptography, A.J. Menezes, CRC Press, ISBN , (free PDF)
PKI, A. Nash et al., RSA Press, ISBN
Foundations of Cryptography, O. Goldereich,
Cryptography in C and C++, M. Welschenbach, Apress, ISBN X (includes code samples CD)

26. Community Resources Community Resources
Most Valuable Professional (MVP)
Newsgroups
Converse online with Microsoft Newsgroups, including Worldwide
/newsgroups/en-us/default.aspx
User Groups - Meet and learn with your peers
default.mspx

27. Strategic Consultant, Project Botticelli Ltd
Thanks to Rafal Lukawiecki for providing some of the content for this presentation deck – his contact details are as follows…
Strategic Consultant, Project Botticelli Ltd
Copyright 2004 © Project Botticelli Ltd & Microsoft Corp. E&OE. For informational purposes only. No warranties of any kind are made and you have to verify all information before relying on it. You can re-use this presentation as long as you read, agree, and follow the guidelines described in the “Comments” field in File/Properties.

28. Common Algorithms

29. DES, IDEA, RC2, RC5, Twofish S/MIME, SSL, Kerberos .NET Fx PGP .NET Fx
Symmetric
DES (Data Encryption Standard) is still the most popular
Keys very short: 56 bits
Brute-force attack took 3.5 hours on a machine costing US$1m in Today it is done real-time
Triple DES (3DES) more secure, but better options about
Just say no, unless value of data is minimal
IDEA (International Data Encryption Standard)
Deceptively similar to DES, and “not” from NSA
128 bit keys
RC2 & RC5 (by R. Rivest)
RC2 is older and RC5 newer (1994) - similar to DES and IDEA
Blowfish, Twofish
B. Schneier’s replacement for DES, followed by Twofish, one of the NIST competition finalists
.NET Fx
PGP
.NET Fx
S/MIME, SSL
Java

30. Rijndael (AES)
.NET Fx
Standard replacement for DES for US government, and, probably for all of us as a result…
Winner of the AES (Advanced Encryption Standard) competition run by NIST (National Institute of Standards and Technology in US) in
Comes from Europe (Belgium) by Joan Daemen and Vincent Rijmen. “X-files” stories less likely (unlike DES).
Symmetric block-cipher (128, 192 or 256 bits) with variable keys (128, 192 or 256 bits, too)
Fast and a lot of good properties, such as good immunity from timing and power (electric) analysis
Construction, again, deceptively similar to DES (S-boxes, XORs etc.) but really different

31. CAST and GOST CAST GOST Canadians Carlisle Adams & Stafford Tavares
64 bit key and 64 bit of data
Chose your S-boxes
Seems resistant to differential & linear cryptanalysis and only way to break is brute force (but key is a bit short!)
GOST
Soviet Union’s “version” of DES but with a clearer design and many more repetitions of the process
256 bit key but really 610 bits of secret, so pretty much “tank quality”
Backdoor? Who knows…

32. Careful with Streams! Do NOT use a block cipher in a loop
Use a crypto-correct technique for treating streams of data, such as CBC (Cipher Block Chaining)
For developers:
.NET Framework implements it as ICryptoTransform on a crypto stream with any supported algorithm

33. RC4 Symmetric PPTP R. Rivest in 1994
Fast, streaming encryption
R. Rivest in 1994
Originally secret, but “published” on sci.crypt
Related to “one-time pad”, theoretically most secure
But!
It relies on a really good random number generator
And that is the problem
Nowadays, we tend to use block ciphers in modes of operation that work for streams
PPTP

34. RSA, DSA, ElGamal, ECC SSL, PGP .NET Fx .NET Fx Asymmetric
Very slow and computationally expensive – need a computer
Very secure
Rivest, Shamir, Adleman – 1978
Popular and well researched
Strength in today’s inefficiency to factorise into prime numbers
Some worries about key generation process in some implementations
DSA (Digital Signature Algorithm) – NSA/NIST thing
Only for digital signing, not for encryption
Variant of Schnorr and ElGamal sig algorithm
ElGamal
Relies on complexity of discrete logarithms
ECC (Elliptic Curve Cryptography)
Really hard maths and topology
Improves RSA (and others)
SSL, PGP
.NET Fx
.NET Fx

35. Quantum Cryptography
Method for generating and passing a secret key or a random stream
Not for passing the actual data, but that’s irrelevant
Polarisation of light (photons) can be detected only in a way that destroys the “direction” (basis)
So if someone other than you observes it, you receive nothing useful and you know you were bugged
Perfectly doable over up-to-120km dedicated long fibre-optic link
Seems pretty perfect, if a bit tedious and slow
Practical implementations still use AES/DES etc. for actual encryption
Magiq QPN:
Don’t confuse it with quantum computing, which won’t be with us for at least another 50 years or so, or maybe longer…

36. MD5, SHA Hash functions – not encryption at all! Goals:
Not reversible: can’t obtain the message from its hash
Hash much shorter than original
Two messages won’t have the same hash
MD5 (R. Rivest)
512 bits hashed into 128
Mathematical model still unknown
But it resisted major attacks
SHA (Secure Hash Algorithm)
US standard based on MD5
S/MIME, SSL,
PGP, Digital Sigs
.NET Fx
.NET Fx

37. Diffie-Hellman, “SSL”, Certs
PGP
Methods for key generation and exchange
DH is very clever since you always generate a new “key-pair” for each asymmetric session
STS, MTI, and certs make it even safer
Certs (certificates) are the most common way to exchange public keys
Foundation of Public Key Infrastructure (PKI)
SSL uses a protocol to exchange keys safely
See later
Everyone

38. Cryptanalysis Brute force Frequency analysis Linear cryptanalysis
Good for guessing passwords, and some 40-bit symmetric keys (in some cases needed only 27 attempts)
Frequency analysis
For very simple methods only (US mobiles)
Linear cryptanalysis
For stronger DES-like, needs 243 plain-cipher pairs
Differential cryptanalysis
Weaker DES-like, needs from 214 pairs
Power and timing analysis
Fluctuations in response times or power usage by CPU

39. Strong Systems It is always a mixture! Changes all the time…
Symmetric:
AES, min. 128 bits for RC2 & RC5, 3DES, IDEA, carefully analysed RC4, 256 bit better
Asymmetric:
RSA, ElGamal, Diffie-Hellman (for keys) with minimum 1024 bits (go for the maximum, typically 4096, if you can afford it)
Hash:
Either MD5 or SHA but with at least 128 bit results, 256 better

40. Weak Systems
Anything with 40-bits (including 128 and 56 bit versions with the remainder “fixed”)
Most consider DES as fairly weak algorithm
CLIPPER
A5 (GSM mobile phones outside US)
Vigenère (US mobile phones)
Dates from 1585!
Unverified certs with no trust
Weak certs (as in many “class 1” personal certs)