1. Gateway Cryptography Hacking Impossible Tunnels Through Improbable Networks with OpenSSH et al. By Dan Kaminsky, CISSP http://www.doxpara.com

2. Summary This is not how to crack SSH. This is SSH on crack. 1) How to get there from here 2) What to do once you get there 3) Making getting there easier

3. The Trinity Of Code Useful –No reason to try Usable –No reason to hurt Well Written –No chance they’ll ever have it If you want to know my theories on the superiority of userspace, ask me later.

4. The Basics Bringing people up to speed –This is not another talk about the wonders of a simple local port forward What OpenSSH does –Forwards a shell (w/ transparent X support) –Forwards a single command (with full stdio) –Forwards a single TCP port “All SSH forwards are non-exclusive and non- transparent figments of userspace”

5. SSH under Windows 1) Install Cygwin from www.cygwin.com 2) Create a shortcut to rxvt –C:\cygwin\bin\rxvt.exe -rv -sl 20000 -fn “Courier- 12" -e /usr/bin/bash bash doesn’t work under whistler yet, so use zsh if you want to retain your tab-completion sanity 3) Finally enjoy a usable Unix environment under Win32 Everything in this talk is cross platform, as long as you’ve made Windows cross to another platform

6. Forwarding Shells ssh user@hostuser@host Encryption: 3DES/Blowfish/AES Authentication: Password, RSA/DSA –Key Generation ssh1: ssh-keygen ssh2: ssh-keygen –t dsa –Key Authorization ssh1: cat ~/.ssh/identity.pub | ssh user@host ‘umask 0600; mkdir.ssh; cat >> authorized_keys’user@host ssh2: cat ~/.ssh/id_dsa.pub | ssh user@host ‘umask 0600; mkdir.ssh; cat >> authorized_keys2’user@host –Separate auth – so remember ssh -1 and ssh -2

7. Forwarding Commands ssh user@host ls ssh –t user@host topuser@host Fully 8 bit clean for most commands, supports (unclean) TTYs for anything that wants to redraw screen (like top) using –t Full STDIO(stdin/stdout/stderr) support –Allows pipelines across multiple systems

8. Command Forwarding: CD Burning Over SSH mkisofs reads in files and spits out a burnable image cdrecord burns the image. –Normal CD Burning mkisofs –JR files | cdrecord dev=#,#,# speed=# - –Remote CD Burning mkisofs –JR files | ssh user@host cdrecord dev=#,#,# speed=# -user@host –Remote CD Burning From Windows mkisofs.exe –JR files | ssh.exe user@host cdrecord dev=#,#,# speed=# -user@host –Remote CD Burning From Windows For Users Right Click On Files/Directories, Click Send To, Click CDR. –Under development; trivial to write

9. Command Forwarding: File Transfer w/o SCP # GET alicehost$ ssh alice@bobhost “cat file” > file # PUT falicehost$ cat file > ssh alice@bobhost “cat > file” # LIST alicehost$ ssh alice@bobhost “ls” # MGET alicehost$ ssh alice@bobhost “tar -cf - /etc” | tar -xf – # RESUME GET alicehost$ ssh alice@bobhost “tail –c 231244 file” >> filealice@bobhost Planning on implementing SFTP using nothing more than these commands SCP is just annoying me more and more, though the syntax is temporarily more convenient

10. Forwarding Ports ssh user@host -L8000:127.0.0.1:80 ssh user@host -R80:127.0.0.1:8000 Separates into “listener” vs. “location” –If local listens, the destination is relative to the remote location –If remote listens, the destination is relative to the local location

11. Limitations on Port Forwards By default, only the systems directly hosting the listener can connect to it –Local forwards can be made public using the –g option, but remote “gateway ports” must be enabled using GatewayPorts Yes Destination locations are unrestricted

12. Accessing a Port Forward Application Layer –Connect Directly to 127.0.0.1 or “localhost” Operating System Layer (“systemspace”) –Pre-empt DNS lookup in hosts file Unix: /etc/hosts Win95: \windows\hosts WinNT: \WINNT\system32\drivers\etc\hosts All forwards must be preannounced, and share the same IP (127.0.0.1)

13. Problem: Static Forwards Are Inflexible Work decently only when: –Each port is only used once Passes: –Mail(smtp, pop3, imap) –Simple Web(HTTP) Fails: –Web Surfing Multiple Sites (HTTP) –P2P File Transfer(Napster, Gnutella), –Ports are predictable in advance Fails miserably –FTP, both Active and Passive

14. Solution: Dynamic Forwarding w/ SOCKS ssh user@host -D1080user@host SOCKS4/5: An in-band protocol header, nothing more, that allows the client to very quickly tell a proxy server where its actual destination was SOCKS4 is extraordinarily simple –~9 bytes from Client, 8 byte response, and the client has informed the “proxy” where it actually wants to go! –“Library Preloads” are excessive The idea: Run a trivial SOCKS daemon in the ssh client; use it to redirect the destination of each channel.

15. Dynamic Forwarding: Application Support Most major Windows applications support SOCKS proxies directly –Internet Explorer, CuteFTP, IM Clients, P2P Clients(Napster, Gnutella) –Dialpad (Voice over IP to a telephone for free over SSH!) SocksCap32 can be used to “Socksify” remaining apps on Windows –Outlook Express, LeechFTP, Media Player, etc. Unix applications can be reasonably socksified too

16. Dynamic Forwarding: Faults In The Hack No Network Isolation –Though this, of course, is “trusting the client”, there’s still value in a client itself volunteering to ignore all communications not through the VPN “solution”. No Unified Configuration and Management Interface –Fixable, should this become popular.

17. Dynamic Forwarding: THE BIG PROBLEM Server Freeze Most SSH servers will temporarily block(lock up) if you attempt to open a channel to a host that either doesn’t exist or cannot be resolved General purpose solutions to this get…ugly. –OpenSSH has fewer problems in this arena OpenSSH has no inherent SOCKS client support – cannot easily connect to dynamic port forwards

18. ProxyCommand: Blind Proxying w/ SSH ssh -o 'ProxyCommand arbitrary_tool proxy %u %h %p' user@10.1.0.1user@10.1.0.1 A ProxyCommand is an arbitrary tool that, after it finishes executing, leads to an 8 bit clean path to an SSH daemon –OpenSSH's excuse for SOCKS support :-) Allows end-to-end crypto through any 8bit clean link –Like SSL over HTTP Connect

19. Wire Mode: Facilitating Self-Proxying SSH ssh user@proxy -Whost:22 ProxyCommand needs an 8 bit path SSH exists to provide 8 bit paths –Correct Method: Open a local port forward, use glue code to directly connect it to ttyless stdio code –Cheap Hack Method: Translate –Whost:22 into “nc host 22”

20. Using netcat-based Wire Mode ssh -o 'ProxyCommand ssh user@proxy "nc %h %p"' user@server Completely unusable Alternative Syntax Under Development –ssh –B proxy user@server –ssh proxy/user@server Competes with: –ssh user@proxy proxy$ ssh user@server The PROXY authenticates The PROXY decrypts The PROXY is Internet accessible If the Proxy gets hacked, the network is toast.

21. No Internet Accessible Bastion Proxy: Now What? proxy$ ssh user@client -R2022:127.0.0.1:22 client$ ssh user@127.0.0.1 -o "HostKeyAlias proxy" -L8000:www-internal:80 or (in upcoming builds, hopefully) client$ ssh user@proxy/2022 -L8000:www-internal:80 Turns inability to trust into irrelevancy of trust –Negative: “You can’t trust the addresses of x, y, or z!” –Positive: “It doesn’t matter if you think you’re talking to the addresses of x, y, or z.” MUST CHECK HOSTKEY – it’ll work even if you don’t

22. Cross-Connecting Mutually Firewalled Hosts server$ ssh proxyuser@proxy -R10022:127.0.0.1:22 client$ ssh -o 'ProxyCommand ssh proxyuser2@proxy ‘nc 127.0.0.1 10022' user@server or in my syntax client$ ssh proxyuser2@proxy/10022 user@serveruser@server Again, as long as IP addresses cannot be trusted, it doesn’t matter that you’re talking to the proxy and connecting through one of its ports.

23. Fixing Port Forwards: Defaults ssh -L143 -> ssh -L143:127.0.0.1:143 ssh -Lfoo -> ssh -L22:foo:22 ssh -R2022: -> ssh -R2022:127.0.0.1:22 Begin with a default of 22:127.0.0.1:22, do some moderately painful string parsing in C, and actually end up with a decently compressed syntax Would forwarding ranges be useful, i.e. ssh -L7000-7020 ?

24. Expanding Escape Syntax noname# ~? Supported escape sequences: ~. - terminate connection ~R - Request rekey (SSH protocol 2 only) ~^Z - suspend ssh ~# - list forwarded connections ~& - background ssh (when waiting for connections to terminate) ~? - this message ~~ - send the escape character by typing it twice (Note that escapes are only recognized immediately after newline.) Eventual goal: Port both ssh_config syntax and ssh command line syntax to the escape character mode –Allow on-demand things like activation of X forwarding

25. Secure SU: The Battle Against Direct Root Most “security gurus” will decry direct root login –Holdover from the battle against admins doing everything as root –SU is a painless enough context switch If it hurts to switch, people will just do it all as root –Advantages to being forced to switch accounts Inertia Emotion – significance of the action is emphasized Accounting – logs show who used root –Even though it essentially reduces the security of the root account to the security of the Alice account, even OpenBSD (2.7, at least) still exhorts users not to ssh directly to root, and instead to use SU.

26. Secure SU: The Near-Perfect Compromise alicehost$ ssh alice@bobhost -t “su –l root” or in my syntax ssh alice+root@bobhost@bobhost SSHD creates a secure execution environment when commands are explicitly specified –Shell configuration files not loaded –su, as a setuid app, can’t generally be traced by ordinary users User logs in as normal, is safely prompted for the root password, gets a root shell without having to “slum” in through insecure space

27. Secure SU: Developing: Individuated Root Individual Public Keys For Root Access –Nobody learns root password authorized_keys contains list of identities allowed to connect as root to the system –SSHD modified to log who connected to root –Scales to multiple security-critical accounts Root can modify its own authorized_keys, but other accounts could have root owned, root readable authorized_keys files. Individual Root Accounts –Multiple accounts all set to same UID, but with different passwords Alice_Root, Bob_Root, etc. –Really only works for root

28. SLIRP/PPTP over SSH: Starting with PPPD PPPD: Standard Unix PPP Server –Generally creates an interface on its host called ppp# –Sets up a bidirectional route—works as an infrastructure-level datapath –Addressing can be manually or automatically negotiated –Standard Dialup Protocol Command Forwarding allows remote PPPD to cleanly talk to local PPPD, thus creating a Host- To-Host VPN between two hosts –Requires root on both –“PPP over SSH”

29. SLIRP/PPTP over SSH: SLIRPing a way SLIRP: User Mode NAT –Written around 1995 –Amazingly useful to this day—doesn’t require root! –Converts any 8 bit clean shell into a PPP server, NATs the incoming TCP/UDP/ICMP and opens the necessary sockets on the shell server –Command Forwarding SLIRP instead of PPPD into local PPPD requires root on only one host, but only the host running PPPD gets an OS-level route Useful, but dangerous--but you’re trusting the server not to replace SLIRP with a hacked version that gives them a path back through your ready-and-willing PPPD.

30. SLIRP/PPTP over SSH: PPP over PPTP PPTP: Point to Point Protocol –Encapsulates PPP(Layer 2) inside of a GRE(Layer 3) Tunnel, allowing TCP/UDP/ICMP(Layer 4) traffic to pass Try not to wrap your brain around this –Created by Microsoft as a VPN Solution Version one was…infamously flawed. Version two is somewhat better, but not widely trusted. Client ships with and is integrated into Windows 98/Me/2000 –Stable Interface –Network Isolation –Good UI –SSH cannot forward GRE internally

31. SLIRP/PPTP over SSH: PoPToP Puts It Together PoPToP: Unix PPTP Daemon –Implements GRE encapsulation only Doesn’t re-implement PPP! Executes PPPD or SLIRP inside of GRE Who says the daemon needs to be local? End Result –Windows 98 connects to user bastion host using PPTP –PoPToP strips GRE header, goes to execute PPP daemon –SSH cleanly forwards a SLIRP command run as a user on a remote bastion host into PoPToP –Windows 98 isolates itself and experiences remote bastion host as a PPTP VPN gateway!

32. SLIRP/PPTP over SSH: HowTo The really lazy way –Used when source is closed but the binary app shells out to some external binary –Really really lazy for PoPToP because it’s open source –mv /usr/bin/slirp slirp_binary echo ‘#!/bin/sh’ >> /usr/bin/slirp echo ‘ssh user@host slirp_binary’ >> /usr/bin/slirp;user@host The less lazy way –Modify PoPToP to execute ‘ssh user@host slirp’ instead of ‘slirp’;user@host Should be noted that there’s *no* authentication to this link inside the PPTP network

33. Conclusion ssh is powerful ssh is flexible ssh is fun. any questions? any requests?