E-Mail Security: CS 470 Introduction To Applied Cryptography Instructor: Ali Aydin Selcuk

E-mail Security
CS 470
Introduction to Applied Cryptography
Instructor: Ali Aydin Selcuk
CS470, A.Selcuk
E-mail Security
Security Services for E-mail
privacy
authentication
integrity
non-repudiation
anonymity
proof of submission
proof of delivery
message flow confidentiality, etc.
CS470, A.Selcuk
E-mail Security
Key Management
A per-message symmetric key is used for
message encryption,
which is conveyed in the mail, encrypted under a
long-term key (typically a public key)
Long-term keys can be established,
offline
online, with help from a trusted third party
online, through a webpage (for public keys)
CS470, A.Selcuk
E-mail Security
Multiple Recipients
Message key will be encrypted under each recipients
long term key in the message header.
Bobs ID, KBob{S}
Carols ID, KCarol{S}
Teds ID, KTed{S}
S{m}
E.g.:
To: Bob, Carol, Ted
From: Alice
Key-info: Bob-4276724736874376
Key-info: Carol-78657438676783457
Key-info: Ted-12873486743009
Msg-info: UHGuiy77t65fhj87oi.....
CS470, A.Selcuk
E-mail Security
Text Format Issues

Mail gateways/forwarders may modify the format
of the message (wrapping long lines, end-of-line
character, high order bits, etc.), causing the
integrity check to fail
Encode messages in a format supported by all
mailers. 6-bit representation, no long lines, etc.
(similar to uuencode)
CS470, A.Selcuk
E-mail Security
Text Format Issues (contd)

Problem: Non-supportive clients should be able
to read authenticated (but not encrypted)
messages, which they no longer can.
Two options:
MAC without encoding
(subject to corruption by mail routers)
Encode & MAC/encrypt
(may not be readable at the other end)
CS470, A.Selcuk
E-mail Security
Providing Different Services
confidentiality: by encryption
auth./integrity: by signature or MAC
non-repudiation: by signature
some eccentric services,
anonymity
message flow confidentiality
non-repudiation with secret keys
can be provided by TTP support.
CS470, A.Selcuk
E-mail Security
PEM & S/MIME

Privacy Enhanced Mail (PEM)
Developed by IETF, to add encryption, source
authentication & integrity protection to e-mail
Allows both public & secret long-term keys
Message key is always symmetric
Specifies a detailed certification hierarchy
Secure/MIME (S/MIME)
PEM never took off; CA hierarchy difficult to realize
S/MIME: PEM design incorporated into MIME
CS470, A.Selcuk
E-mail Security
PEM Key Exchange & Encryption

Interchange keys: Users long-term PEM keys
public (a detailed PKI is defined)
secret (pre-shared symmetric keys)
Encryption
A symmetric per-message key is sent encrypted under
the interchange key.
The message is encrypted under the per-message key
(typically with DES in CBC mode)
Authentication
Message is authenticated by a MIC
(Q: Any authentication for the per-message key?)
CS470, A.Selcuk
E-mail Security
PEM Certificate Hierarchy

The root CA: Internet Policy Registration Authority
(IPRA)
Policy Certification Authorities: Second-level, CAcertifying CAs, each with a different policy:
High Assurance (HA): super-secure
implemented on secure platforms
regulates that the child CAs (also HACAs) enforce the same rules
Discretionary Assurance (DA): secure

requires that the child CAs own their names
No Assurance (NA): no constraints

can be used to certify Internet personas (pseudonyms)
Lower-level CAs, certifying individuals or other CAs

CS470, A.Selcuk
E-mail Security
10
S/MIME vs. PEM

Incorporated into MIME; no other encoding
Any sequence of sign & encrypt is supported
(each as a recursive MIME encapsulation)
Has more options than PEM
ASN.1 header encoding
No prescribed certification hierarchy
Has a good prospect of deployment for
commercial & organizational usage
CS470, A.Selcuk
E-mail Security
11
Pretty Good Privacy (PGP)

Popular mail & file encryption tool
Developed by Phil Zimmermann, 1991
Based on RSA, IDEA, MD5 (later DSS, ElGamal
(DH), 3DES, SHA1)
Many different versions have emerged (from
PGP, from GNU (GPG), from IETF (Open PGP))
CS470, A.Selcuk
E-mail Security
12
PGP Operation
All long-term user keys are public
Signature:
Message & timestamp are hashed (MD5 or SHA1) and
signed (RSA or DSS)
Compression (ZIP)
Encryption:
Message is encrypted with a per-message symmetric
key (typically with IDEA in CFB mode)
which is encrypted with the recipients public key
(RSA or DH (ElGamal))
Radix-64 (6-bit) encoding

CS470, A.Selcuk
E-mail Security
13
Trust Model & Key Management

Any user can certify any other (anarchy model)
Each user decides whom to trust and how much
Key Ring: Data structure to store public keys
held by a user, with their levels of trust
Public keys can be obtained,
offline (in person, over the phone, etc.)

through personal webpages
through a trusted friend (web of trust)
through a trusted CA
CS470, A.Selcuk
E-mail Security
14
DKIM Domain Keys Identified Mail

An effort to stop spam with forged domain
addresses (e.g. phishing attacks).
Standardized by RFC 4871; supported by Yahoo,
Gmail, FastMail etc.
Each domain has an email signature key.
Public keys will be retrieved over DNS.
If signature verification fails, mail will be dropped.
CS470, A.Selcuk
E-mail Security
15
DKIM
Once deployed, it will significantly limit phishing
attacks with forged domain addresses.
Deployment is increasing rapidly.
Example: Gmails collaboration with PayPal &
eBay
CS470, A.Selcuk
E-mail Security
16

E-Mail Security: CS 470 Introduction To Applied Cryptography Instructor: Ali Aydin Selcuk

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E-Mail Security: CS 470 Introduction To Applied Cryptography Instructor: Ali Aydin Selcuk

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E-mail Security

Security Services for E-mail

Text Format Issues

Text Format Issues (contd)

Providing Different Services

can be provided by TTP support.

PEM & S/MIME

PEM Key Exchange & Encryption

PEM Certificate Hierarchy

Discretionary Assurance (DA): secure

No Assurance (NA): no constraints

Lower-level CAs, certifying individuals or other CAs

S/MIME vs. PEM

Pretty Good Privacy (PGP)

Radix-64 (6-bit) encoding

Trust Model & Key Management

offline (in person, over the phone, etc.)

DKIM Domain Keys Identified Mail

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