Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS...

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Black Hat USA 2007 Tactical Exploitation Tactical Exploitation “ “ the other way to pen-test “ the other way to pen-test “ hdm / valsmith hdm / valsmith

Transcript of Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS...

Page 1: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

Tactical ExploitationTactical Exploitation““the other way to pen-test “the other way to pen-test “

hdm / valsmithhdm / valsmith

Page 2: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

who are we ?who are we ?

H D Moore <hdm [at] metasploit.com>

BreakingPoint Systems || Metasploit

Valsmith <valsmith [at] metasploit.com>

Offensive Computing || Metasploit

Page 3: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

why listen ?why listen ?• A different approach to pwning

• New tools, fun techniques

• Real-world tested :-)

Page 4: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

what do we cover ?what do we cover ?• Target profiling

• Discovery tools and techniques

• Exploitation• Getting you remote access

Page 5: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

the tactical approachthe tactical approach• Vulnerabilites are transient

• Target the applications• Target the processes• Target the people• Target the trusts

• You WILL gain access.

Page 6: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

the tactical approachthe tactical approach• Crackers are opportunists

• Expand the scope of your tests• Everything is fair game

• What you dont test...• Someone else will.

Page 7: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

the tactical approachthe tactical approach• Hacking is not about exploits

• The target is the data, not r00t

• Hacking is using what you have• Passwords, trust relationships• Service hijacking, auth tickets

Page 8: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery• Security is a people problem

• People write your software• People secure your network

• Identify the meatware first

Page 9: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery• Identifying the meatware

• Google• Newsgroups• SensePost tools• www.Paterva.com

Page 10: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery• These tools give us

• Full names, usernames, email• Employment history• Phone numbers• Personal sites

Page 11: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery

CASE STUDY

Page 12: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery• Started with no information but CO

name and function

• Found online personnel directory

• Found people / email addresses

• Email name = username = target

Page 13: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

personnel discoverypersonnel discovery

DEMO

Page 14: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery• Identify your target assets

• Find unknown networks• Find third-party hosts

• Dozens of great tools...• Lets stick to the less-known ones

Page 15: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery• The overused old busted

• Whois, Google, zone transfers• Reverse DNS lookups

Page 16: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery• The shiny new hotness

• Other people's services• CentralOps.net• DigitalPoint.com• DomainTools.com• Paterva.com

Page 17: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery• What does this get us?

• Proxied DNS probes, transfers• List of virtual hosts for each IP• Port scans, traceroutes, etc• Gold mine of related info

Page 18: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery• Active discovery techniques

• Trigger SMTP bounces• Brute force HTTP vhosts• Watch outbound DNS• Just email the users!

Page 19: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery

CASE STUDY

Page 20: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

network discoverynetwork discovery

DEMO

Page 21: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

firewalls and ipsfirewalls and ips• Firewalls have gotten snobby

• Content filtering is now common• Intrusion prevention is annoying

• Identify and fingerprint• Increase your stealthiness• Customize your exploits

Page 22: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

firewalls and ipsfirewalls and ips• Firewall identification

• NAT device source port ranges• Handling of interesting TCP

• IPS identification• Use “drop with no alert” sigs• Traverse sig tree to find vendor

Page 23: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

firewall and ipsfirewall and ips

CASE STUDY

Page 24: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

firewall and ipsfirewall and ips

DEMO

Page 25: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery• If the network is the toast...• Applications are the butter.

• Each app is an entry point• Finding these apps is the trick

Page 26: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery• Tons of great tools

• Nmap, Amap, Nikto, Nessus• Commercial tools

Page 27: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery• Slow and steady wins the deface

• Scan for specific port, one port only

• IDS/IPS can't handle slow scans• Ex. nmap -sS -P0 -T 0 -p 1433 ips

Page 28: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery• Example target had custom IDS to

detect large # of host connections

• Standard nmap lit up IDS like XMAS

• One port slow scan never detected

• Know OS based on 1 port (139/22)

Page 29: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery• Some new tools

• W3AF for locating web apps• Metasploit 3 includes scanners

Page 30: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery

CASE STUDY

Page 31: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

application discoveryapplication discovery

DEMO

Page 32: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery• Client applications are fun!

• Almost always exploitable• Easy to fingerprint remotely• Your last-chance entrance

Page 33: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery• Common probe methods

• Mail links to the targets• Review exposed web logs• Send MDNs to specific victims• Abuse all, everyone, team aliases

Page 34: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery• Existing tools

• BEEF for browser fun• Not much else...

Page 35: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery• Shiny new tools

• Metasploit 3 SMTP / HTTP• Metasploit 3 SMB services

Page 36: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery

CASE STUDY

Page 37: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

client app discoveryclient app discovery

DEMO

Page 38: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

process discoveryprocess discovery• Track what your target does

• Activity via IP ID counters• Last-modified headers• FTP server statistics

Page 39: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

process discoveryprocess discovery• Look for patterns of activity

• Large IP ID increments at night• FTP stats at certain times• Web pages being uploaded

Page 40: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

process discoveryprocess discovery• Existing tools?

• None :-(

• New tools• Metasploit 3 profiling modules• More on exploiting this later...

Page 41: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

process discoveryprocess discovery

CASE STUDY

Page 42: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

process discoveryprocess discovery

DEMO

Page 43: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

15 Minute Break15 Minute Break• Come back for the exploits!

Page 44: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

re-introductionre-introduction• In our last session...

• Discovery techniques and tools

• In this session...• Compromising systems!

Page 45: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

external networkexternal network• The crunchy candy shell

• Exposed hosts and services• VPN and proxy services• Client-initiated sessions

Page 46: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

attacking file transfersattacking file transfers• FTP transfers

• Active FTP source ports• Passive FTP servers

• NFS transfers• TFTP transfers

Page 47: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

attacking mail servicesattacking mail services• Four different attack points

• The mail relay servers• The antivirus gateways• The real mail server• The users mail client

• File name clobbering...

Page 48: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

attacking web serversattacking web servers• Brute force files and directories• Brute force virtual hosts• Standard application flaws• Load balancer fun...• Clueless users cgi-bin's are often

the Achilles heel

Page 49: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

attacking dns serversattacking dns servers• Brute force host name entries• Brute force internal hosts• XID sequence analysis• Return extra answers...

Page 50: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

attacking db serversattacking db servers• Well-known user/pass combos

• Business apps hardcode auth

• Features available to anonymous• No-patch bugs (DB2, Ingres, etc)

Page 51: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

authentication relaysauthentication relays• SMB/CIFS clients are fun!

• Steal hashes, redirect, MITM

• NTLM relay between protocols• SMB/HTTP/SMTP/POP3/IMAP

Page 52: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

social engineeringsocial engineering• Give away free toys

• CDROMs, USB keys, N800s

• Replace UPS with OpenWRT• Cheap and easy to make

Page 53: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

internal networkinternal network• The soft chewy center

• This is the fun part :)• Easy to trick clients

Page 54: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services• SMB is awesome

• Look for AFP exports of SMB data

• NAS storage devices• Rarely, if ever, patch Samba :-)

Page 55: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services• NFS is your friend

• Dont forget its easy cousin NIS

• Scan for port 111 / 2049• showmount -e / showmount -a• Whats exported, whose mounting?

Page 56: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services• Exported NFS home directories

• Important target!

• If you get control• Own every node that mounts it

Page 57: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services• If you are root on home server

• Become anyone (NIS/su)• Harvest known_hosts files• Harvest allowed_keys• Modify .login, etc. + insert trojans

Page 58: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services• Software distro servers are fun!

• All nodes access over NFS• Write to software distro directories• Trojan every node at once• No exploits needed!

Page 59: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

file servicesfile services

CASE STUDY

Page 60: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

netbios servicesnetbios services• NetBIOS names are magic

• WPAD• ISASRV• CALICENSE

Page 61: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

dns servicesdns services• Microsoft DNS + DHCP = fun

• Inject and overwrite DNS• Hijack the entire network• Impersonate servers

Page 62: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

wins serviceswins services• Advertise your WINS service

• Control name lookups• Attack other client apps

Page 63: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

license serverslicense servers• A soft spot in desktop apps

• Computer Associates• Bugs and simple to spoof

• FlexLM network services

Page 64: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

remote desktopsremote desktops• RDP

• Great for gathering other targets• Domain lists available pre-auth• If not available, start your own:

• net start “terminal services”

Page 65: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

remote desktopsremote desktops• VNC

• The authentication bug is great :)• MITM attacks are still viable• Install your own with Metasploit 3

• vncinject payloads

Page 66: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

trust relationshipstrust relationships• The target is unavailable to YOU

• Not to another host you can reach...

• Networks may not trust everyone• But they often trust each other :)

•

Page 67: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

trust relationshipstrust relationships

CASE STUDY

Page 68: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

Hijacking SSHHijacking SSH

CASE STUDY

Page 69: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

Hijacking KerberosHijacking Kerberos

CASE STUDY

Page 70: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

Hijacking NTLMHijacking NTLM

CASE STUDY

Page 71: Tactical Exploitation · Black Hat USA 2007 application discovery • Example target had custom IDS to detect large # of host connections • Standard nmap lit up IDS like XMAS •

Black Hat USA 2007

ConclusionConclusion• Compromise a patched network

• Determination / creativity wins

• Lots of new pen-test tools

• The best tool is still YOU!


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