Man in the middle attacks
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1 Alberto Ornaghi Marco Valleri Man in the middle attacks What they are How to achieve them How to use them How to prevent them Blackhat Conference - Europe
2 Table of contents Different attacks in different scenarios: LOCAL AREA NETWORK: - ARP poisoning - DNS spoofing - Port stealing - STP mangling FROM LOCAL TO REMOTE (through a gateway): - ARP poisoning - DNS spoofing - DHCP spoofing - ICMP redirection - IRDP spoofing - route mangling REMOTE: - DNS poisoning - traffic tunneling - route mangling Blackhat Conference - Europe
3 Once in the middle... Blackhat Conference - Europe
4 Sniffing It is the easiest attack to launch since all the packets transit through the attacker. All the Òplain textó protocols are compromised (the attacker can sniff user and password of many widely used protocol such as telnet, ftp, http) Blackhat Conference - Europe
5 Hijacking Easy to launch It isnõt t blind (the attacker knows exactly the sequence numbers of the TCP connection) Blackhat Conference - Europe
6 Injecting Possibility to add packets to an already established connection (only possible in full-duplex mitm) The attacker can modify the sequence numbers and keep the connection synchronized while injecting packets. If the mitm attack is a Òproxy attackó it is even easier to inject (there are two distinct connections) Blackhat Conference - Europe
7 Filtering The attacker can modify the payload of the packets by recalculating the checksum He/she can create filters on the fly The length of the payload can also be changed but only in full-duplex (in this case the seq has to be adjusted) Blackhat Conference - Europe
8 Attacks examples Blackhat Conference - Europe
9 Attacks examples (1) Command injection Useful in scenarios where a one time authentication is used (e.g. RSA token). In such scenarios sniffing the password is useless, but hijacking an already authenticated session is critical Injection of commands to the server Emulation of fake replies to the client Blackhat Conference - Europe
10 Attacks examples (2) Malicious code injection Insertion of malicious code into web pages or mail (javascript( javascript, trojans,, virus, ecc) Modification on the fly of binary files during the download phase (virus, backdoor, ecc) Blackhat Conference - Europe
11 Attacks examples (3) Key exchanging Modification of the public key exchanged by server and client.. (eg( SSH1) start Server Client KEY(rsa) MITM KEY(rsa) S-KEY E key [S-Key] S-KEY E key [S-Key] S-KEY M E skey (M) D(E(M)) D(E(M)) Blackhat Conference - Europe
12 Attacks examples (4) Parameters and banners substitution Parameters exchanged by server and client can be substituted in the beginning of a connection. (algorithms to be used later) Example: the attacker can force the client to initialize a SSH1 connection instead of SSH2. Ð The server replies in this way: SSH the server supports ssh1 and ssh2 SSH the server supports ONLY ssh1 Ð The attacker makes a filter to replace Ò1.99Ó with Ò1.51Ó Possibility to circumvent known_hosts Blackhat Conference - Europe
13 Attacks examples (5) IPSEC Failure Block the keymaterial exchanged on the port 500 UDP End points think that the other cannot start an IPSEC connection If the client is configured in rollback mode, there is a good chance that the user will not notice that the connection is in clear text Blackhat Conference - Europe
14 Attacks examples (6) PPTP (1) - description Uses GRE as transport layer (no encryption, no authentication) Uses the same negotiation scheme as PPP (req, ack, nak, rej) Negotiation phases are not authenticated MS-CHAPv2 mutual authentication canõt prevent this kind of mitm Blackhat Conference - Europe
15 Attacks examples (6) PPTP (2) - attacks During negotiation phase Ð Force PAP authentication (almost fails) Ð Force MS-CHAPv1 from MS-CHAPv2 (easier to crack) Ð Force no encryption Force re-negotiation (clear text terminate-ack ack) Ð Retrieve passwords from existing tunnels Ð Perform previous attacks Force Òpassword changeó to obtain password hashes Ð Hashes can be used directly by a modified SMB or PPTP client Ð MS-CHAPv2 hashes are not usefull (you can force v1) Blackhat Conference - Europe
16 Attacks examples (6) PPTP (3) - attack example Force PAP from CHAP Server req auth chap MITM start Client req auth fake nak auth pap nak auth chap req auth pap req auth pap ack auth pap ack auth pap We donõt have to mess with GRE sequences... Blackhat Conference - Europe
17 Attacks examples (6) PPTP (4) - L2TP rollback L2TP can use IPSec ESP as transport layer (stronger than PPTP) By default L2TP is tried before PPTP Blocking ISAKMP packets results in an IPSec failure Client starts a request for a PPTP tunnel (rollback) Now you can perform PPTP previous attacks Blackhat Conference - Europe
18 Attacks examples (6) PPTP (5) - tools Ettercap Ð Hydra plugins suite Anger ( Anger ( Blackhat Conference - Europe
19 Attack techniques LOCAL SCENARIO Blackhat Conference - Europe
20 Local Attacks (1) ARP poisoning ARP is stateless (we all knows how it works and what the problems are) Some operating systems do not update an entry if it is not already in the cache, others accept only the first received reply (e.g( solaris) The attacker can forge a spoofed ICMP packets to force the host to make an ARP request. Immediately after the ICMP it sends the fake ARP replay Request attack against linux (IDS evasion) Blackhat Conference - Europe
21 Local Attacks (1) ARP poisoning Useful to sniff on switched LANs The switch works at layer 2 and it is not aware of the poisoning in the hostsõ ARP cache (unless some ARP inspection) Blackhat Conference - Europe
22 Local Attacks (1) ARP poisoning - tools Ettercap ( Ð Poisoning Ð Sniffing Ð Hijacking Ð Filtering Ð SSH sniffing (transparent( attack) Ettercap Dsniff ( Ð Poisoning Ð Sniffing Ð SSH sniffing (proxy( attack) Dsniff Blackhat Conference - Europe
23 Local Attacks (1) ARP poison - countermeasures YES - passive monitoring (arpwatch) YES - active monitoring (ettercap) YES - IDS (detect but not avoid) YES - Static ARP entries (avoid it) YES - Secure-ARP (public key auth) NO - Port security on the switch NO - anticap,, antidote, middleware approach Blackhat Conference - Europe
24 Local Attacks (2) DNS spoofing If the attacker is able to sniff the ID of the DNS request, he/she can reply before the real DNS server HOST MITM serverx.localdomain.it DNS Blackhat Conference - Europe
25 Local Attacks (2) DNS spoofing - tools Ettercap ( Ettercap Ð Phantom plugin Dsniff ( Dsniff Ð Dnsspoof Zodiac ( Blackhat Conference - Europe
26 Local Attacks (2) DNS spoofing - countermeasures YES - detect multiple replies (IDS) YES - use lmhost or host file for static resolution of critical hosts YES - DNSSEC Blackhat Conference - Europe
27 Local Attacks (3) STP mangling It is not a real MITM attack since the attacker is able to receive only ÒunmanagedÓ traffic The attacker can forge BPDU with high priority pretending to be the new root of the spanning tree Blackhat Conference - Europe
28 Local Attacks (3) STP mangling - tools Ettercap ( Ð Lamia plugin Blackhat Conference - Europe
29 Local Attacks (3) STP mangling - countermeasures YES - Disable STP on VLAN without loops YES - Root Guard, BPDU Guard. Blackhat Conference - Europe
30 Local Attacks (4) Port stealing The attacker sends many layer 2 packets with: Ð Source address equal to victim hostsõ address Ð Destination address equal to its own mac address The attacker now has ÒstolenÓ victim hostsõ ports When the attacker receives a packet for one of the victims it generates a broadcast ARP request for the victimõs s IP address. When the attacker receives the ARP reply from the victim, the victimõs s port has been restored to the original binding state The attacker can now forward the packet and restart the stealing process Blackhat Conference - Europe
31 Local Attacks (4) Port stealing - tools Ettercap ( Ð Confusion plugin Blackhat Conference - Europe
32 Local Attacks (4) Port stealing - countermeasures YES - port security on the switch NO - static ARP Blackhat Conference - Europe
33 Attack techniques FROM LOCAL TO REMOTE Blackhat Conference - Europe
34 Local to remote attacks (1) DHCP spoofing The DHCP request are made in broadcast. If the attacker replies before the real DHCP server it can manipulate: Ð IP address of the victim Ð GW address assigned to the victim Ð DNS address Blackhat Conference - Europe
35 Local to remote attacks (1) DHCP spoofing - countermeasures YES - detection of multiple DHCP replies Blackhat Conference - Europe
36 Local to remote attacks (2) ICMP redirect The attacker can forge ICMP redirect packet in order to Redirect traffic to himself T G1 ICMP redirect to AT AT H LAN Blackhat Conference - Europe
37 Local to remote attacks (2) ICMP redirect - tools IRPAS icmp_redirect (Phenoelit) ( icmp_redir (Yuri Volobuev) Blackhat Conference - Europe
38 Local to remote attacks (2) ICMP redirect - countermeasures YES - Disable the ICMP REDIRECT NO - Linux has the Òsecure redirectó options but it seems to be ineffective against this attack Blackhat Conference - Europe
39 Local to remote attacks (3) IRDP spoofing The attacker can forge some advertisement packet pretending to be the router for the LAN. He/she can set the Òpreference leveló and the ÒlifetimeÓ at high values to be sure the hosts will choose it as the preferred router. The attack can be improved by sending some spoofed ICMP Host Unreachable pretending to be the real router Blackhat Conference - Europe
40 Local to remote attacks (3) IRDP spoofing - tools IRPAS by Phenoelit ( Blackhat Conference - Europe
41 Local to remote attacks (3) IRDP spoofing - countermeasures YES - Disable IRDP on hosts if the operating system permit it. Blackhat Conference - Europe
42 Local to remote attacks (4) ROUTE mangling INTERNET GW AT H The attacker can forge packets for the gateway (GW) pretending to be a router with a good metric for a specified host on the internet The netmask should be big enough to win against other routes Blackhat Conference - Europe
43 Local to remote attacks (4) ROUTE mangling Now the problem for the attacker is to send packets to the real destination. He/she cannot send it through GW since it is convinced that the best route is AT. Tunnel AT2 D INTERNET GW AT Blackhat Conference - Europe H
44 Local to remote attacks (4) ROUTE mangling - tools IRPAS (Phenoelit) ( Nemesis ( Blackhat Conference - Europe
45 Local to remote attacks (4) ROUTE mangling - countermeasures YES - Disable dynamic routing protocols on this type of scenarios YES - Enable some ACL to block unexpected update YES - Enable authentications on the protocols that support them Blackhat Conference - Europe
46 Attacks techniques REMOTE SCENARIOS Blackhat Conference - Europe
47 Remote attacks (1) DNS poisoning Type 1 attack Ð The attacker sends a request to the victim DNS asking for one host Ð The attacker spoofs the reply which is expected to come from the real DNS Ð The spoofed reply must contain the correct ID (brute force or semi-blind guessing) Blackhat Conference - Europe
48 Remote attacks (1) DNS poisoning Type 2 attack Ð The attacker can send a Òdynamic updateó to the victim DNS Ð If the DNS processes it, it is even worst because it will be authoritative for those entries Blackhat Conference - Europe
49 Remote attacks (1) DNS poisoning - tools ADMIdPack Zodiac ( Blackhat Conference - Europe
50 (1) Remote attacks (1) DNS poisoning - countermeasures YES - Use DNS with random transaction ID (Bind v9) YES - DNSSec (Bind v9) allows the digital signature of the replies. NO - restrict the dynamic update to a range of IP (they can be spoofed) Blackhat Conference - Europe
51 (2) Remote attacks (2) Traffic Tunneling Server Router 1 Tunnel GRE INTERNET Client Fake host Attacker Gateway Blackhat Conference - Europe
52 (2) Remote attacks (2) Traffic Tunneling - tools Ettercap ( Ettercap Ð Zaratan plugin TunnelX ( Blackhat Conference - Europe
53 (2) Remote attacks (2) Traffic Tunneling - countermeasure YES - Strong passwords and community on routers Blackhat Conference - Europe
54 (3) Remote attacks (3) ROUTE mangling The attacker aims to hijack the traffic between the two victims A and B The attack will collect sensitive information through: Ð traceroute Ð portscanning Ð protoscanning Quite impossible against link state protocols Blackhat Conference - Europe
55 (3) Remote attacks (3) ROUTE mangling Scenario 1 a (IGRP inside the AS) A R1 B R2 The attacker pretends to be the GW Blackhat Conference - Europe
56 (3) Remote attacks (3) ROUTE mangling Scenario 1 b (IGRP inside the AS) A R1 R3 B R2 Blackhat Conference - Europe
57 (3) Remote attacks (3) ROUTE mangling Scenario 2 a (the traffic does not pass thru the AS) AS 1 AS 2 BGP BG 1 BG 2 BG 3 AS 3 RIP Blackhat Conference - Europe
58 (3) Remote attacks (3) ROUTE mangling IRPAS di Phenoelit ( Nemesis ( Blackhat Conference - Europe
59 (3) Remote attacks (3) ROUTE mangling - countermeasure YES - Use routing protocol authentications Blackhat Conference - Europe
60 Conclusions The security of a connection relies on: Ð a proper configuration of the client (avoiding ICMP Redirect, ARP Poisoning etc.) Ð the other endpoint infrastructure (es( es.. DNS dynamic update), Ð the strongness of a third party appliances on which we donõt have access (es( es. Tunnelling and Route Mangling). The best to protect a communication is the correct and conscious use of criptographic suites Ð both client and server side Ð at the network layer (ie( ie. IPSec) Ð at transport layer (ie( ie.. SSLv3) Ð at application layer (ie( ie.. PGP). Blackhat Conference - Europe
61 Ð Marco Valleri Ð Alberto Ornaghi Blackhat Conference - Europe
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