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Sniffing SSL Traffic

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Sniffing SSL Traffic
Challenges ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],SSL
Question ? ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
Symmetric Encryption ,[object Object],[object Object],[object Object],[object Object]
Asymmetric Encryption ,[object Object],[object Object],[object Object],[object Object]
Hashing / Message Digest ,[object Object],[object Object],[object Object],[object Object],[object Object],4fe7ad41
Message Signing ,[object Object],[object Object],[object Object],4fe7ad41 3e7bc46a 4fe7ad41 4fe7ad41 3e7bc46a = ?
Digital Certificates ,[object Object],[object Object],[object Object]
Certificate Authorities ,[object Object],[object Object],[object Object],[object Object]
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
SSL History ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Place in TCP/IP stack ,[object Object],[object Object],IP TCP HTTP SMTP … SSL/TLS SSL record layer handshake change cipherspec application data alert
SSL Record Layer ,[object Object],[object Object],[object Object],[object Object]
SSL Content Types ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
Choosing the right settings
Analyzing the SSL handshake ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Normal RSA handshake Client Server ServerHello ClientHello Certificate ServerHelloDone ClientKeyExchange ChangeCipherSpec Finished (encrypted) ChangeCipherSpec Finished (encrypted)
First packet…
Analyzing the SSL record layer (1)
Random
Session ID
Cipher Suites
Server name
Server Hello
Certificate Message
Server’s Certificate
Server Hello Done
Certificate Validation
Client Key Exchange
Finally Application Data
Ephemeral RSA (or DH) handshake Client Server ServerHello ClientHello Certificate ServerHelloDone ClientKeyExchange ChangeCipherSpec Finished (encrypted) ChangeCipherSpec Finished (encrypted) ServerKeyExchange
Server Key Exchange
Server Key Exchange
Client Authentication Client Server ServerHello ClientHello Certificate ServerHelloDone Certificate ClientKeyExchange Finished (encrypted) ChangeCipherSpec Finished (encrypted) CertificateRequest CertificateVerify ChangeCipherSpec
Client Certificate Request
Certificate Request
Certificate (C)
Certificate Verify
Caching SSL sessions ,[object Object],[object Object],[object Object],[object Object],[object Object]
Handshake of a Reused Session Client Server ServerHello ClientHello ChangeCipherSpec Finished (encrypted) ChangeCipherSpec Finished (encrypted)
SSL session reuse (new, reused and expired) Full Handshake Partial Handshake
No SSL session caching
Analyzing SSL alerts Without decryption: With decryption:
Decrypting SSL traffic ,[object Object],[object Object],[object Object],[object Object]
Providing the server private key (1) tshark -r file.cap -o ssl.keys_list:192.168.3.3,443,http,"c:ey.pem" -o ssl.debug_file:"c:sl-debug.log" -V -R http ssl.keys_list: 192.168.3.3,443,http,c:ey.pem ssl.debug_file: c:empsl-debug.log Wireshark preferences file: When using Tshark:
[object Object],[object Object],[object Object],Providing the server private key (2) PEM keyfile *with* passphrase: -----BEGIN RSA PRIVATE KEY----- Proc-Type: 4,ENCRYPTED DEK-Info: DES-EDE3-CBC,F6C218D4FA3C8B66 FR2cnmkkFHH45Dcsty1qDiIUy/uXn+9m/xeQMVRxtiSAmBmnUDUFIFCDDiDc9yif ERok2jPr2BzAazl5RBxS2TY/+7x0/dHD11sF3LnJUoNruo77TERxqgzOI0W1VDRA ... ygw5JslxgiN18F36E/cEP5rKvVYvfEPMa6IsiRhfZk1jLAuZihVWc7JodDf+6RKV yBXrK/bDtdEih+bOnYu+ZDvjAzVz9GhggCW4QHNboDpTxrrYPkj5Nw== -----END RSA PRIVATE KEY----- PEM keyfile *without* passphrase: -----BEGIN RSA PRIVATE KEY----- MIICXgIBAAKBgQDrHdbb+yGE6m6EZ03bXURpZCjch2H6g97ZAkJVGrjLZFfettBA EYa8vYYxWsf8KBpEZeksSCsDA9MnU2H6QDjzqdOnaSWfeXMAr4OsCOpauStpreq7 q1hk8iOqy+f4KijRrhWplh1QW1A8gtSIg137pyUhW+WsfwxKwmzjGIC1SwIDAQAB AoGBAMneA9U6KIxjb+JUg/99c7h9W6wEvTYHNTXjf6psWA+hpuQ82E65/ZJdszL6 ... b6QKMh16r5wd6smQ+CmhOEnqqyT5AIwwl2RIr9GbfIpTbtbRQw/EcQOCx9wFiEfo tGSsEFi72rHK+DpJqRI9AkEA72gdyXRgPfGOS3rfQ3DBcImBQvDSCBa4cuU1XJ1/ MO93a8v9Vj87/yDm4xsBDsoz2PyBepawHVlIvZ6jDD0aXw== -----END RSA PRIVATE KEY----- ssl_init keys string: 192.168.3.3,443,http,c:empublic.sharkfest.local.key ssl_init found host entry 192.168.3.3,443,http,c:empublic.sharkfest.local.key ssl_init addr '192.168.3.3' port '443' filename 'c:empublic.sharkfest.local.key' password(only for p12 file) '(null)' ssl_load_key: can't import pem data SSL debug log:
Converting keys root@mgmt# openssl rsa -in encrypted.key -out cleartext.key Enter pass phrase for encrypted.key: <passphrase> writing RSA key root@mgmt# root@mgmt# openssl pkcs12 -in pem.cert -inkey pem.key -export -out cert.pkcs12 Enter Export Password: <new-passphrase> Verifying - Enter Export Password: <new-passphrase> root@mgmt# root@mgmt# openssl rsa -inform DER -in der.key -out pem.key Enter pass phrase for encrypted.key: <passphrase> writing RSA key root@mgmt# Removing passphrase: Converting from DER to PEM (and removing passphrase): Converting from PEM to PKCS12 (and adding passphrase):
Decryption in Action
Agenda ,[object Object],[object Object],[object Object],[object Object],[object Object]
Preparation of the proxy ,[object Object],[object Object],[object Object],[object Object],[object Object],[object Object],[object Object]
Man in the middle starts ,[object Object],[object Object]
SSL Strip ,[object Object],[object Object]
Screenshot from browser…
Here is the user and password from logs Tail –f sslstrip.log
Questions & Discussion ? ? ? ? ? ? ? ? ? ? ? ? ? ?
Thank you…

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Sniffing SSL Traffic

Notas do Editor

  1. Mostly used for bulk encryption How to exchange keys?
  2. public-private key Mostly used for secure key exchanges How to verify keys?