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Add JCSA17 TLS notebooks

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mtu 2017-08-22 11:37:07 +02:00
parent 3d113a9162
commit e398df053b
31 changed files with 890 additions and 0 deletions
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{
"cells": [
{
"cell_type": "markdown",
"metadata": {},
"source": [
"# Notebook 1: X.509 certificates"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## Jupyter notebook cheat sheet"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Use Shift+Enter to run the current cell\n",
"print 'Hello!'"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# You may also use Alt+Enter to run the current cell, then create a new cell right below\n",
"from datetime import datetime\n",
"print 'This is the time right now: %s' % datetime.now()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# If needed, pause the cell edition with Ctrl-M.\n",
"# Then you can delete the current cell with D+D. You can also undo cell deletion with Z.\n",
"# Finally, should Jupyter become stuck in execution, use Kernel/Interrupt from the menu bar.\n",
"print 'Got it!'"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## Data manipulation with Scapy"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"from scapy.all import *"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"keystr = open('raw_data/pki/ca_key.der', 'r').read()\n",
"print repr(keystr)\n",
"# (btw, you can hide the output of a cell by double-clicking on the left of the output)"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"privkey = RSAPrivateKey(keystr)\n",
"privkey.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"v = privkey.version\n",
"print 'The \\'version\\' stripped from any ASN.1 encoding is 0x%02x.' % v.val\n",
"print 'The \\'version\\' field correspond to bytes %r.' % str(v)"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"privkey.version = ASN1_INTEGER(1)\n",
"privkey.modulus.val *= 2\n",
"privkey.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"print 'Original data: %r...' % keystr[:13]\n",
"print 'New version bytes: %r' % str(privkey.version)\n",
"print 'New modulus bytes: %r...' % str(privkey.modulus)[:6]\n",
"print 'Rebuilt data: %r...' % str(privkey)[:13]"
]
},
{
"cell_type": "markdown",
"metadata": {
"collapsed": true
},
"source": [
"## X.509 certificate features"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Let's reload the original key, then let's load a certificate associated with it\n",
"privkey = RSAPrivateKey(keystr)\n",
"cert = X509_Cert(open('raw_data/pki/ca_cert.der', 'r').read())\n",
"cert.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"cert.tbsCertificate.subjectPublicKeyInfo.subjectPublicKey.show()\n",
"cert.tbsCertificate.subject[-1].rdn[0].show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false,
"scrolled": true
},
"outputs": [],
"source": [
"cert.tbsCertificate.subjectPublicKeyInfo.subjectPublicKey.modulus == privkey.modulus"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"cert.tbsCertificate.extensions[2].show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"cert.signatureAlgorithm.algorithm"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## Scapy crypto tools"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"# Let's reload the key with Scapy's crypto-enhanced wrapper\n",
"privkey = PrivKey('raw_data/pki/ca_key.der')"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"privkey.der == keystr"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"print privkey.key\n",
"print privkey.pubkey"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# We can compute the RSA signature over the part of the certificate which is to be signed\n",
"privkey.sign(str(cert.tbsCertificate))"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"cert.signatureValue"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# We can quickly modify a certificate field and update the signature accordingly\n",
"cert.tbsCertificate.serialNumber.val = 0xdeadcafe\n",
"cert.tbsCertificate.subject[-1].rdn[0].value.val = 'my new deadcafe CA' \n",
"cert2 = privkey.resignCert(cert)\n",
"cert2.show()"
]
}
],
"metadata": {
"kernelspec": {
"display_name": "Python 2",
"language": "python",
"name": "python2"
},
"language_info": {
"codemirror_mode": {
"name": "ipython",
"version": 2
},
"file_extension": ".py",
"mimetype": "text/x-python",
"name": "python",
"nbconvert_exporter": "python",
"pygments_lexer": "ipython2",
"version": "2.7.13"
}
},
"nbformat": 4,
"nbformat_minor": 2
}

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{
"cells": [
{
"cell_type": "markdown",
"metadata": {},
"source": [
"# TLS handshake overview\n",
"This is the standard, modern TLS 1.2 handshake:\n",
"\n",
"<img src=\"images/handshake_tls12.png\" alt=\"Handshake TLS 1.2\" width=\"400\"/>"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"# We're going to parse several successive records from the passive listening of a standard TLS handshake\n",
"from scapy.all import *"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) ---> (S) ClientHello"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record1 = TLS(open('raw_data/tls_session_protected/01_cli.raw').read())\n",
"record1.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"for extension in record1.msg[0].ext:\n",
" print ''\n",
" extension.show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) <--- (S) ServerHello"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record2 = TLS(open('raw_data/tls_session_protected/02_srv.raw').read())\n",
"record2.show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) <--- (S) Certificate"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record3 = TLS(open('raw_data/tls_session_protected/03_srv.raw').read())\n",
"record3.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# The Certificate message actually contains a *chain* of certificates\n",
"for cert in record3.msg[0].certs:\n",
" print type(cert[1])\n",
" cert[1].show()\n",
" print ''"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Let's recall the domain that the client wants to access\n",
"record1.msg[0].ext[0].show()\n",
"\n",
"# Indeed the certificate may be used with other domains than its CN 'www.github.com'\n",
"x509c = record3.msg[0].certs[0][1].x509Cert\n",
"print type(x509c)\n",
"x509c.tbsCertificate.extensions[2].show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) <--- (S) CertificateStatus, ServerKeyExchange, ServerHelloDone"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Here the server sent three TLS records in the same TCP segment\n",
"record4 = TLS(open('raw_data/tls_session_protected/04_srv.raw').read())\n",
"record4.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Let's verify the signature in the ServerKeyExchange\n",
"# First, we need to assemble the whole data being signed\n",
"cli_random = pkcs_i2osp(record1.msg[0].gmt_unix_time, 4) + record1.msg[0].random_bytes\n",
"srv_random = pkcs_i2osp(record2.msg[0].gmt_unix_time, 4) + record2.msg[0].random_bytes\n",
"ecdh_params = str(record4[TLSServerKeyExchange].params)\n",
"\n",
"# Then we retrieve the server's Cert and verify the signature\n",
"cert_srv = record3.msg[0].certs[0][1]\n",
"cert_srv.verify(cli_random + srv_random + ecdh_params, record4[TLSServerKeyExchange].sig.sig_val, h='sha512')"
]
},
{
"cell_type": "markdown",
"metadata": {
"collapsed": true
},
"source": [
"## (C) ---> (S) ClientKeyExchange, ChangeCipherSpec, Finished"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record5_str = open('raw_data/tls_session_protected/05_cli.raw').read()\n",
"record5 = TLS(record5_str)\n",
"record5.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"# Every record has a 'tls_session' context which may enhance the parsing of later records\n",
"record5 = TLS(record5_str, tls_session=record2.tls_session.mirror())\n",
"record5.show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) <--- (S) NewSessionTicket, ChangeCipherSpec, Finished"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record6_str = open('raw_data/tls_session_protected/06_srv.raw').read()\n",
"record6 = TLS(record6_str, tls_session=record5.tls_session.mirror())\n",
"record6.show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## (C) ---> (S) ApplicationData"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record7_str = open('raw_data/tls_session_protected/07_cli.raw').read()\n",
"record7 = TLS(record7_str, tls_session=record6.tls_session.mirror())\n",
"record7.show()"
]
}
],
"metadata": {
"kernelspec": {
"display_name": "Python 2",
"language": "python",
"name": "python2"
},
"language_info": {
"codemirror_mode": {
"name": "ipython",
"version": 2
},
"file_extension": ".py",
"mimetype": "text/x-python",
"name": "python",
"nbconvert_exporter": "python",
"pygments_lexer": "ipython2",
"version": "2.7.13"
}
},
"nbformat": 4,
"nbformat_minor": 2
}

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{
"cells": [
{
"cell_type": "markdown",
"metadata": {},
"source": [
"# The lack of PFS: a danger to privacy"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"from scapy.all import *"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record1_str = open('raw_data/tls_session_compromised/01_cli.raw').read()\n",
"record1 = TLS(record1_str)\n",
"record1.msg[0].show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false,
"scrolled": true
},
"outputs": [],
"source": [
"record2_str = open('raw_data/tls_session_compromised/02_srv.raw').read()\n",
"record2 = TLS(record2_str, tls_session=record1.tls_session.mirror())\n",
"record2.msg[0].show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"# Suppose we possess the private key of the server\n",
"# Try registering it to the session\n",
"#key = PrivKey('raw_data/pki/srv_key.pem')\n",
"#record2.tls_session.server_rsa_key = key"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record3_str = open('raw_data/tls_session_compromised/03_cli.raw').read()\n",
"record3 = TLS(record3_str, tls_session=record2.tls_session.mirror())\n",
"record3.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record4_str = open('raw_data/tls_session_compromised/04_srv.raw').read()\n",
"record4 = TLS(record4_str, tls_session=record3.tls_session.mirror())\n",
"record4.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": false
},
"outputs": [],
"source": [
"record5_str = open('raw_data/tls_session_compromised/05_cli.raw').read()\n",
"record5 = TLS(record5_str, tls_session=record4.tls_session.mirror())\n",
"record5.show()"
]
}
],
"metadata": {
"kernelspec": {
"display_name": "Python 2",
"language": "python",
"name": "python2"
},
"language_info": {
"codemirror_mode": {
"name": "ipython",
"version": 2
},
"file_extension": ".py",
"mimetype": "text/x-python",
"name": "python",
"nbconvert_exporter": "python",
"pygments_lexer": "ipython2",
"version": "2.7.13"
}
},
"nbformat": 4,
"nbformat_minor": 2
}

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{
"cells": [
{
"cell_type": "markdown",
"metadata": {},
"source": [
"# TLS 1.3 handshake overview\n",
"This is the basic TLS 1.3 handshake:\n",
"\n",
"<img src=\"images/handshake_tls13.png\" alt=\"Handshake TLS 1.3\" width=\"400\"/>"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"from scapy.all import *"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {},
"outputs": [],
"source": [
"record1_str = open('raw_data/tls_session_13/01_cli.raw').read()\n",
"record1 = TLS(record1_str)\n",
"sess = record1.tls_session\n",
"record1.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {},
"outputs": [],
"source": [
"record2_str = open('raw_data/tls_session_13/02_srv.raw').read()\n",
"record2 = TLS(record2_str, tls_session=sess.mirror())\n",
"record2.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {},
"outputs": [],
"source": [
"record3_str = open('raw_data/tls_session_13/03_cli.raw').read()\n",
"record3 = TLS(record3_str, tls_session=sess.mirror())\n",
"record3.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"collapsed": true
},
"outputs": [],
"source": [
"# The PFS relies on the ECDH secret below being kept from observers, and deleted right after the key exchange\n",
"#from cryptography.hazmat.primitives.asymmetric.ec import EllipticCurvePrivateNumbers\n",
"#from cryptography.hazmat.backends import default_backend\n",
"#secp256r1_client_privkey = open('raw_data/tls_session_13/cli_key.raw').read()\n",
"#pubnum = sess.tls13_client_pubshares[\"secp256r1\"].public_numbers()\n",
"#privnum = EllipticCurvePrivateNumbers(pkcs_os2ip(secp256r1_client_privkey), pubnum)\n",
"#privkey = privnum.private_key(default_backend())\n",
"#sess.tls13_client_privshares[\"secp256r1\"] = privkey"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {
"scrolled": true
},
"outputs": [],
"source": [
"record4_str = open('raw_data/tls_session_13/04_srv.raw').read()\n",
"record4 = TLS(record4_str, tls_session=sess.mirror())\n",
"record4.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {},
"outputs": [],
"source": [
"record5_str = open('raw_data/tls_session_13/05_srv.raw').read()\n",
"record5 = TLS(record5_str, tls_session=sess)\n",
"record5.show()"
]
},
{
"cell_type": "code",
"execution_count": null,
"metadata": {},
"outputs": [],
"source": [
"record6_str = open('raw_data/tls_session_13/06_cli.raw').read()\n",
"record6 = TLS(record6_str, tls_session=sess.mirror())\n",
"record6.show()"
]
},
{
"cell_type": "markdown",
"metadata": {},
"source": [
"## Observations sur TLS 1.3\n",
"* Certificat désormais chiffré...\n",
"* ...mais pas le Server Name dans le ClientHello\n",
"* Risques du mode 0-RTT"
]
}
],
"metadata": {
"kernelspec": {
"display_name": "Python 2",
"language": "python",
"name": "python2"
},
"language_info": {
"codemirror_mode": {
"name": "ipython",
"version": 2
},
"file_extension": ".py",
"mimetype": "text/x-python",
"name": "python",
"nbconvert_exporter": "python",
"pygments_lexer": "ipython2",
"version": "2.7.13"
}
},
"nbformat": 4,
"nbformat_minor": 2
}

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-----BEGIN CERTIFICATE-----
MIIDnjCCAoagAwIBAgIJAP4EVw3HJ+n2MA0GCSqGSIb3DQEBCwUAMFQxCzAJBgNV
BAYTAk1OMRQwEgYDVQQHDAtVbGFhbmJhYXRhcjEXMBUGA1UECwwOU2NhcHkgVGVz
dCBQS0kxFjAUBgNVBAMMDVNjYXB5IFRlc3QgQ0EwHhcNMTYwOTE2MTAyODExWhcN
MjYwOTE1MTAyODExWjBYMQswCQYDVQQGEwJNTjEUMBIGA1UEBwwLVWxhYW5iYWF0
YXIxFzAVBgNVBAsMDlNjYXB5IFRlc3QgUEtJMRowGAYDVQQDDBFTY2FweSBUZXN0
IFNlcnZlcjCCASIwDQYJKoZIhvcNAQEBBQADggEPADCCAQoCggEBAMzx8ZtgLWCu
8pgNJynZwAlZTA9KMKhS3+WxIZ9Pwz1Wk91fxvez9lWL55Li3vKFSbShLPT9dqhn
ygQgYBEYpvKptqYd2arl2duv5q9VV5//Uoll5oBigCGUvM+BG8tnwp21BXcEpseI
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-----END CERTIFICATE-----

28
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-----BEGIN PRIVATE KEY-----
MIIEvAIBADANBgkqhkiG9w0BAQEFAASCBKYwggSiAgEAAoIBAQDM8fGbYC1grvKY
DScp2cAJWUwPSjCoUt/lsSGfT8M9VpPdX8b3s/ZVi+eS4t7yhUm0oSz0/XaoZ8oE
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SuoPn2VvTqmhiwSuATdx1TP4XOVdVzuL2wT7brS7qHvabRDBKdVOfrNGOoMdnnua
ursIQjQindNT8kVK8EGxws9eFr/dooYYFR72IusTfQKBgQDuQBzzKEtt86uRCbZX
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aieZ5rec7qmbzOFxVLz6e03/Ipo5CEoQQTsjoF7V74SFHSyzQ2/SJao4aeCGT+52
83yhlah9sLO9bZShMep2tbvg+3RWrOQ+lMC0VRXCxE4QDtpGsjY7Jsk/AoGAPstV
iOa4O6U/rBn8zpcPKxkS51u42MuQqW7s4HMLENFVyVjm0YR6pfEqztKMrB6584Wk
1Cn6PBW2vx4f+fAqEvX7x340M2y1r7DaS22gSBjy0C1Hu0rFNPRrESo/AUVlI3BG
RqQbm0YqwcYs+DjZi8bgc7HX5kljlzMjo8QLagECgYA1DHAWv4WVrHt4I8V4ZCth
9DZEtEOFpYjuoFh/xSIMZLsnvWRuyYVWcQwAqmK0Ew4m5opHFsQzABeGLVsK5aHX
zmbYiRUuZGVpyc7c5XXomw50X8ajfQ+P21OPPc33h96cdHi2qbJIejZPia6A6ThU
u13D93hAM6bzH6Ds5FPUQw==
-----END PRIVATE KEY-----

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<11>H<EFBFBD>S<EFBFBD><17>؝<EFBFBD>`<60>6&]9<><39><EFBFBD>-vmB<6D><42>N<EFBFBD>

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