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TLS in five minutes
#MeraKrypto
@oej * oej@edvina.net

v 1.1 2014-05-06
#MoreCrypto
Identity
Security basics.
Confidentiality
Authorization
Integrity
Non-repudiation
#MoreCrypto
TLS is an important tool
TLS
Transport

Layer

Security
TLS provides confidentiality, identity

and integrity to Internet communication.
TLS is used in HTTPS:// web pages, but can also be
used from applications on a computer as well as a cell
phone.
TLS is based on SSL, that was a provider-specific
technology. TLS is maintained by the IETF and is still
being improved.
TLS basics in a minute
• TLS use a keypair to set up a secure connection
• Assymetric encryption
• The server sends the public key at connection
• The client challenges the server
• The server responds to the challenge using the
server private key
• Now the client knows that the server has the
private key that matches the public key
private
TLS Usage
• TLS is used for 	

• authentication of servers and
clients	

• initiating encryption of a session	

• digital signatures on messages to
ensure integrity and provide
authentication
Authentication
Who are you? Prove it!
Encryption
Providing confidentiality
Integrity
Making sure that the
receiver get what the
sender sent
Adding a certificate to the
mix
• A certificate is nothing more complicated than a
passport or an ID card
• It contains the public key and some administrative
data
• And is signed (electronically) by someone you
might trust ... or not.
• This is part of the complex structure called PKI,
which you might want or just disregard
• A PKI is not needed to get encryption for the
signalling path!
• You can however use a PKI to only set up
connections that you trust
The X.509v3 certificate
• An X.509 certificate is the standardised way to

bind a public key to an identity
• The certificate is issued by a 

Certification Authority (CA)
• The most important component of the PKI?
• An X.509 certificate is an 

electronic document with a specific layout
!
• Standard: documented in IETF PKIX RFC:s
Version
Serial number
Issuer identity
Validity period
User identity
Public key
Extension fields
X509.v3

contents
• Version number
• Certificate serial number

Used for validation
• Identity of the issuer
• Validity period
• Identity of the public key owner
• Public key
• Extension fields
• A digital signature, created by the issuer
Internet

Explorer

Certificate

Manager
SIP certificates
• SubjectAltName contains a list of identities that
are valid for this certificate
• draft-ietf-certs outlines a SIP event package to
distribute and manage certificates
• This is based on the Authentication Service in SIP
identity (RFC 4474)
• The domain cert is used to sign the NOTIFY
payload
x.509 cert for SIP
Certificate:	

Data:	

Version: 3 (0x2)	

Serial Number:	

01:08:00:79:00:15:00:43	

Signature Algorithm: sha1WithRSAEncryption	

Issuer: C=US, ST=California, L=San Jose, O=sipit, OU=SipitTest Certificate Authority	

Validity	

Not Before: Sep 16 17:17:00 2009 GMT	

Not After : Sep 15 17:17:00 2012 GMT	

Subject: C=US, ST=California, L=San Jose, O=sipit, CN=tls6.test.sipit.net	

Subject Public Key Info:	

Public Key Algorithm: rsaEncryption	

RSA Public Key: (2048 bit)	

Modulus (2048 bit):	

00:a7:96:65:6e:b6:ba:3a:48:a1:bd:a3:ae:21:dc:	

a8:92:97:3c:43:ea:24:e6:9f:93:2f:61:7e:d3:2d:	

30:1e:21:42:b9:d6:59:87:f1:b1:f8:c8:39:8e:43:	

64:9a:31:2c:18:3d:cd:d8:03:64:bb:14:38:44:05:	

20:30:d8:e1:db:a7:4d:c3:47:a2:49:73:d1:10:ed:	

2f:cf:74:26:57:91:64:af:b0:f2:5d:3f:88:9f:df:	

65:6c:ba:65:3f:66:99:52:6b:20:d2:0e:e3:65:18:	

b1:8e:3d:ca:f2:4a:45:c5:4d:85:ef:82:54:f8:54:	

54:db:96:90:9b:c5:1b:2a:1e:60:3c:43:71:55:60:	

30:93:8f:fd:d8:d9:3d:a1:32:e3:56:4b:e2:73:b6:	

cc:18:93:8a:d8:8b:68:81:c7:fd:cd:d5:dc:4c:a2:	

86:61:9f:ad:d0:b1:d3:3c:4c:6c:07:54:b2:43:b4:	

a7:0a:0a:f2:e3:6d:12:43:16:70:63:c9:e9:1a:78:	

66:9d:ee:30:94:7b:ab:f2:e9:67:4a:66:6d:8c:ed:	

a8:a4:98:51:77:0b:a7:60:55:73:85:87:4a:57:6b:	

24:fe:27:00:02:79:70:da:5a:45:ad:aa:3d:d5:40:	

5b:5c:85:63:93:56:af:c7:e8:e3:b6:1a:25:b6:a2:	

2d:37	

Exponent: 65537 (0x10001)	

X509v3 extensions:	

X509v3 Subject Alternative Name: 	

DNS:test.sipit.net, DNS:tls6.test.sipit.net, URI:sip:tls6.test.sipit.net	

X509v3 Basic Constraints: 	

CA:FALSE	

X509v3 Subject Key Identifier: 	

27:F7:A9:96:F5:B2:8F:0B:5E:A9:C7:F5:0F:AC:3D:AB:3D:8D:F0:30	

Signature Algorithm: sha1WithRSAEncryption	

1a:fe:1f:af:86:99:82:e5:14:97:8d:64:9a:d1:5c:ea:6c:96:	

f5:c6:0c:7d:20:5f:4e:70:05:24:3a:de:b5:b9:cf:66:8d:4c:	

74:d5:6a:a9:52:74:17:bc:b4:79:a0:58:32:78:a9:70:7c:6a:	

15:ac:07:29:77:13:06:55:53:3f:0b:4c:3d:da:55:6e:ad:74:	

56:01:55:c8:4c:19:8d:06:0b:f3:4c:04:d5:9a:6f:44:ad:7a:	

fd:3b:aa:e8:4b:84:6e:f1:c4:34:f4:a0:6a:f6:81:ae:74:b4:	

46:6e:b9:2f:a6:59:f1:02:e9:58:7c:a1:8d:08:31:2b:39:ee:	

eb:7e	

Subject: C=US, ST=California, L=San Jose, O=sipit, CN=tls6.test.sipit.net
X509v3 Subject Alternative Name: 	

DNS:test.sipit.net, DNS:tls6.test.sipit.net, URI:sip:tls6.test.sipit.net
Process for a server
Generate

Keys
Pack public key

in CSR
Send CSR

to CA
CA validate

process
CA issues 

Certificate
Install cert

in server with

private key
Client connection
Open TCP

connection
Server sends

certificate
Client

challenge server
Server answers

challenge
Client validates

certificate
Server can issue

cert request
Client and server
produce session key
Symmetric encryption
starts
Protocol specifics
• Given a protocol request - how do we match the
request address to a certificate
• SIP Uri, E-mail address, HTTPS uri
User specifics
• Which CAs do we trust?
• How do we check validity of certificate, even if
we trust the CA?
• Do we have time for validation?
New solutions
• Anchoring the certificate in DNS
• Validating the certificate in DNS
• No certificate - bare keys
• Oppurtunistic Security with TLS

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#MoreCrypto : Introduction to TLS

  • 1. TLS in five minutes #MeraKrypto @oej * oej@edvina.net
 v 1.1 2014-05-06
  • 3. #MoreCrypto TLS is an important tool TLS Transport
 Layer
 Security TLS provides confidentiality, identity
 and integrity to Internet communication. TLS is used in HTTPS:// web pages, but can also be used from applications on a computer as well as a cell phone. TLS is based on SSL, that was a provider-specific technology. TLS is maintained by the IETF and is still being improved.
  • 4. TLS basics in a minute • TLS use a keypair to set up a secure connection • Assymetric encryption • The server sends the public key at connection • The client challenges the server • The server responds to the challenge using the server private key • Now the client knows that the server has the private key that matches the public key private
  • 5. TLS Usage • TLS is used for • authentication of servers and clients • initiating encryption of a session • digital signatures on messages to ensure integrity and provide authentication Authentication Who are you? Prove it! Encryption Providing confidentiality Integrity Making sure that the receiver get what the sender sent
  • 6. Adding a certificate to the mix • A certificate is nothing more complicated than a passport or an ID card • It contains the public key and some administrative data • And is signed (electronically) by someone you might trust ... or not. • This is part of the complex structure called PKI, which you might want or just disregard • A PKI is not needed to get encryption for the signalling path! • You can however use a PKI to only set up connections that you trust
  • 7. The X.509v3 certificate • An X.509 certificate is the standardised way to
 bind a public key to an identity • The certificate is issued by a 
 Certification Authority (CA) • The most important component of the PKI? • An X.509 certificate is an 
 electronic document with a specific layout ! • Standard: documented in IETF PKIX RFC:s Version Serial number Issuer identity Validity period User identity Public key Extension fields
  • 8. X509.v3
 contents • Version number • Certificate serial number
 Used for validation • Identity of the issuer • Validity period • Identity of the public key owner • Public key • Extension fields • A digital signature, created by the issuer Internet
 Explorer
 Certificate
 Manager
  • 9. SIP certificates • SubjectAltName contains a list of identities that are valid for this certificate • draft-ietf-certs outlines a SIP event package to distribute and manage certificates • This is based on the Authentication Service in SIP identity (RFC 4474) • The domain cert is used to sign the NOTIFY payload
  • 10. x.509 cert for SIP Certificate: Data: Version: 3 (0x2) Serial Number: 01:08:00:79:00:15:00:43 Signature Algorithm: sha1WithRSAEncryption Issuer: C=US, ST=California, L=San Jose, O=sipit, OU=SipitTest Certificate Authority Validity Not Before: Sep 16 17:17:00 2009 GMT Not After : Sep 15 17:17:00 2012 GMT Subject: C=US, ST=California, L=San Jose, O=sipit, CN=tls6.test.sipit.net Subject Public Key Info: Public Key Algorithm: rsaEncryption RSA Public Key: (2048 bit) Modulus (2048 bit): 00:a7:96:65:6e:b6:ba:3a:48:a1:bd:a3:ae:21:dc: a8:92:97:3c:43:ea:24:e6:9f:93:2f:61:7e:d3:2d: 30:1e:21:42:b9:d6:59:87:f1:b1:f8:c8:39:8e:43: 64:9a:31:2c:18:3d:cd:d8:03:64:bb:14:38:44:05: 20:30:d8:e1:db:a7:4d:c3:47:a2:49:73:d1:10:ed: 2f:cf:74:26:57:91:64:af:b0:f2:5d:3f:88:9f:df: 65:6c:ba:65:3f:66:99:52:6b:20:d2:0e:e3:65:18: b1:8e:3d:ca:f2:4a:45:c5:4d:85:ef:82:54:f8:54: 54:db:96:90:9b:c5:1b:2a:1e:60:3c:43:71:55:60: 30:93:8f:fd:d8:d9:3d:a1:32:e3:56:4b:e2:73:b6: cc:18:93:8a:d8:8b:68:81:c7:fd:cd:d5:dc:4c:a2: 86:61:9f:ad:d0:b1:d3:3c:4c:6c:07:54:b2:43:b4: a7:0a:0a:f2:e3:6d:12:43:16:70:63:c9:e9:1a:78: 66:9d:ee:30:94:7b:ab:f2:e9:67:4a:66:6d:8c:ed: a8:a4:98:51:77:0b:a7:60:55:73:85:87:4a:57:6b: 24:fe:27:00:02:79:70:da:5a:45:ad:aa:3d:d5:40: 5b:5c:85:63:93:56:af:c7:e8:e3:b6:1a:25:b6:a2: 2d:37 Exponent: 65537 (0x10001) X509v3 extensions: X509v3 Subject Alternative Name: DNS:test.sipit.net, DNS:tls6.test.sipit.net, URI:sip:tls6.test.sipit.net X509v3 Basic Constraints: CA:FALSE X509v3 Subject Key Identifier: 27:F7:A9:96:F5:B2:8F:0B:5E:A9:C7:F5:0F:AC:3D:AB:3D:8D:F0:30 Signature Algorithm: sha1WithRSAEncryption 1a:fe:1f:af:86:99:82:e5:14:97:8d:64:9a:d1:5c:ea:6c:96: f5:c6:0c:7d:20:5f:4e:70:05:24:3a:de:b5:b9:cf:66:8d:4c: 74:d5:6a:a9:52:74:17:bc:b4:79:a0:58:32:78:a9:70:7c:6a: 15:ac:07:29:77:13:06:55:53:3f:0b:4c:3d:da:55:6e:ad:74: 56:01:55:c8:4c:19:8d:06:0b:f3:4c:04:d5:9a:6f:44:ad:7a: fd:3b:aa:e8:4b:84:6e:f1:c4:34:f4:a0:6a:f6:81:ae:74:b4: 46:6e:b9:2f:a6:59:f1:02:e9:58:7c:a1:8d:08:31:2b:39:ee: eb:7e Subject: C=US, ST=California, L=San Jose, O=sipit, CN=tls6.test.sipit.net X509v3 Subject Alternative Name: DNS:test.sipit.net, DNS:tls6.test.sipit.net, URI:sip:tls6.test.sipit.net
  • 11. Process for a server Generate
 Keys Pack public key
 in CSR Send CSR
 to CA CA validate
 process CA issues 
 Certificate Install cert
 in server with
 private key
  • 12. Client connection Open TCP
 connection Server sends
 certificate Client
 challenge server Server answers
 challenge Client validates
 certificate Server can issue
 cert request Client and server produce session key Symmetric encryption starts
  • 13. Protocol specifics • Given a protocol request - how do we match the request address to a certificate • SIP Uri, E-mail address, HTTPS uri
  • 14. User specifics • Which CAs do we trust? • How do we check validity of certificate, even if we trust the CA? • Do we have time for validation?
  • 15. New solutions • Anchoring the certificate in DNS • Validating the certificate in DNS • No certificate - bare keys • Oppurtunistic Security with TLS