SSH The Secure Shell
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1 June 26, 2007 UniForum Chicago SSH The Secure Shell Hemant Shah Platform: Linux and Unix
2 What is SSH? June 26, 2007 Copyright Hemant Shah 2
3 What is SSH? The Secure Shell It is a protocol not a product Software based approach to network security Encrypts the data sent between the computers Client/Server architecture Comes with all Linux distribution, Mac OS X, AIX, Sun Solaris, OpenBSD and other Unix variants Ported to other operating systems, such as Windows, Palm OS, Amiga, etc. Other clients, such as, scp, sftp, etc. are also available Replacement for telnet, rlogin, rsh, rcp, ftp, etc. June 26, 2007 Copyright Hemant Shah 3
4 What is SSH Not June 26, 2007 Copyright Hemant Shah 4
5 What SSH is NOT It is not a true shell like csh, ksh, sh, etc. It is not a command interpreter It creates secure channel for running commands on remote computer It is not a complete security solution It will not protect against trojans, viruses, etc. June 26, 2007 Copyright Hemant Shah 5
6 History June 26, 2007 Copyright Hemant Shah 6
7 History In 1995, Tatu Ylönen, a researcher at Helsinki University designed the first version of the protocol (now called SSH-1) In July of 1995, he released SSH1 as free software In December of 1995 he formed SSH Communication Security to market and develop SSH In 1996 SSH-2 was developed, it was incompatible with SSH-1 SCS released SSH-2 in 1998 and had more restrictive license IETF formed group called SECSH to standardize the protocol OpenSSH, free implementation of SSH-2 protocol was released from OpenBSD project. In 2006 IETF SECSH group released SSH-2 as internet standard (RFC 4251) June 26, 2007 Copyright Hemant Shah 7
8 Terminology June 26, 2007 Copyright Hemant Shah 8
9 Terminology SSH - Generic term used for SSH protocols ssh - Client command for running remote command sshd - Server program SSH-1 - Version 1 of the protocol SSH-2 - Version 2 of the protocol OpenSSH - Product from open BSD project June 26, 2007 Copyright Hemant Shah 9
10 SSH Architecture June 26, 2007 Copyright Hemant Shah 10
11 SSH Architecture ssh client ssh server Authentication Network June 26, 2007 Copyright Hemant Shah 11
12 SSH Layers ssh-connection Session multiplexing, X11 and port forwarding, remote command execution, SOCKS proxy, etc. Application Layer Transport Layer Internet Layer Network Access Layer ssh-userauth User authentication using public key, password, host based, etc. ssh-transport Initial key exchange and server authentication, setup encryption TCP IP Ethernet June 26, 2007 Copyright Hemant Shah 12
13 SSH Connection Sequence A cryptographic handshake is made with the server The connection between client and remote server is encrypted using symmetric cipher Client authenticates itself Client can now interact safely with remote server over encrypted connection June 26, 2007 Copyright Hemant Shah 13
14 SSH Features Strong encryption Strong authentication Authorization Integrity of communication Forwarding or tunneling June 26, 2007 Copyright Hemant Shah 14
15 SSH will protect against Eavesdropping of data transmitted over the network Manipulation of data at intermediate elements in the network (e.g. routers) IP address spoofing where an attack hosts pretends to be a trusted host by sending packets with the source address of the trusted host DNS spoofing of trusted host names/ip addresses IP source routing June 26, 2007 Copyright Hemant Shah 15
16 SSH will not protect against Incorrect configuration or usage A compromised root account If you login from a host to a server and an attacker has control of root on either side, he/she can listen to your session by reading from the pseudo-terminal device, even though SSH is encrypted on the network, SSH must communicate in clear text with the terminal device Insecure home directories: if an attacker can modify files in your home directory (e.g. via NFS) he may be able to fool SSH June 26, 2007 Copyright Hemant Shah 16
17 Installing SSH June 26, 2007 Copyright Hemant Shah 17
18 Downloading Source Code You may download the source from Read installation instructions to check if you have pre-requisite packages and libraries. June 26, 2007 Copyright Hemant Shah 18
19 Building and installing OpenSSH gtar -xzf openssh-4.5p1.tar.gz cd openssh-4.5p1./configure make make install June 26, 2007 Copyright Hemant Shah 19
20 Configuration files June 26, 2007 Copyright Hemant Shah 20
21 SSH Configuration Files SSH has two different sets of configuration files System wide configuration files User specific configuration files June 26, 2007 Copyright Hemant Shah 21
22 System wide configuration files The system wide configuration are stored in /etc/ssh directory ssh_config - Client configuration file. It is overridden by configuration file in user's home directory sshd_config - Configuration file for sshd server daemon ssh_host_dsa_key - The DSA private key used by the sshd daemon ssh_host_dsa_key.pub - The DSA public key used by the sshd daemon ssh_host_rsa_key - The RSA private key used by the sshd daemon for version 2 of the SSH protocol ssh_host_rsa_key.pub - The RSA public key used by the sshd for version 2 of the SSH protocol June 26, 2007 Copyright Hemant Shah 22
23 System wide configuration files sshd.pid - Server's PID is stored in this file June 26, 2007 Copyright Hemant Shah 23
24 User specific configuration files The user specific configuration files are stored in ~UserName/.ssh directory authorized_keys2 - This file holds a list of authorized public keys for users. When the client connects to a server, the server authenticates the client by checking its signed public key stored within this file id_dsa - Contains the DSA private key of the user id_dsa.pub - The DSA public key of the user id_rsa - The RSA private key of the user id_rsa.pub - The RSA public key of the user known_hosts - This file contains DSA host keys of SSH servers accessed by the user. This file is very important for ensuring that the SSH client is connecting the correct SSH server June 26, 2007 Copyright Hemant Shah 24
25 User specific configuration files config - Client configuration file June 26, 2007 Copyright Hemant Shah 25
26 Configuration files Specify authentication methods supported Specify SSH protocols supported Need to make trade-offs between security and easy-of use Behavior of the server can be controlled in following order: Compiling time configuration Configuration file Command line options June 26, 2007 Copyright Hemant Shah 26
27 Configuration file syntax Server configuration is stored in /etc/ssh/sshd_config file Client configuration is stored in /etc/ssh/ssh_config and ~/.ssh/config files. The file contains two types of entries Comment or blank line Key/Value pair Example: # This is a comment line Port 22 June 26, 2007 Copyright Hemant Shah 27
28 Server Recommendations June 26, 2007 Copyright Hemant Shah 28
29 Server recommendations Protocol Possible values are 1 or 2 Protocol 2 Protocol 1 has been deprecated because of vulnerabilities, it is recommended that you do not support protocol 1. June 26, 2007 Copyright Hemant Shah 29
30 Server recommendations Port Possible values are any integer less than Port 22 June 26, 2007 Copyright Hemant Shah 30
31 Server recommendations ListenAddress IP address of the system and optionally port number ListenAddress ListenAddress :12345 By default sshd will listen to all network interfaces, if you want to limit sshd to service only certain interface then use this option. June 26, 2007 Copyright Hemant Shah 31
32 Server recommendations TCPKeepAlive Send TCP keepalive messages TCPKeepAlive yes If keepalive messages are not sent then server may not realize that the client has crashed. It will keep running and use resources. However, this means that connections will die if the route is down temporarily. June 26, 2007 Copyright Hemant Shah 32
33 Server recommendations Compression CompressionLevel Compression yes CompressionLevel 6 Not needed on intranet. June 26, 2007 Copyright Hemant Shah 33
34 Server recommendations IgnoreRhosts IgnoreRhosts yes June 26, 2007 Copyright Hemant Shah 34
35 Server recommendations UsePrivilegeSeparation UsePrivilegeSeparation yes Separates privileges by creating an unprivileged child process to deal with incoming network traffic. June 26, 2007 Copyright Hemant Shah 35
36 Server recommendations PermitRootLogin PermitRootLogin no Specifies whether root can login using ssh. The argument must be ``yes'', ``without-password'', ``forced-commands-only'' or ``no''. The default is ``yes''. June 26, 2007 Copyright Hemant Shah 36
37 Server recommendations Subsystem Subsystem sftp /usr/local/libexec/sftp-server Configures external subsystem (e.g. sftp server). June 26, 2007 Copyright Hemant Shah 37
38 Client Recommendations June 26, 2007 Copyright Hemant Shah 38
39 Client recommendations Host Host hostname or wildcard pattern. Restricts the following configuration, up to the next Host keyword, to the matching host(s). June 26, 2007 Copyright Hemant Shah 39
40 Client recommendations BatchMode BatchMode no If set to yes, passphrase/password querying is disabled. This option is useful in scripts and other batch jobs. June 26, 2007 Copyright Hemant Shah 40
41 Client recommendations ForwardX11 ForwardX11 yes June 26, 2007 Copyright Hemant Shah 41
42 Client recommendations ForwardX11Trusted ForwardX11Trusted yes If the this option is set to ``yes'' then remote X11 clients will have full access to the original X11 display. If this option is set to ``no'' then remote X11 clients will be considered untrusted and prevented from stealing or tampering with data belonging to trusted X11 clients. June 26, 2007 Copyright Hemant Shah 42
43 Client recommendations IdentityFile IdentityFile /path/to/private/key/file June 26, 2007 Copyright Hemant Shah 43
44 Client recommendations HostName HostName real hostname or IP address Specifies the real host name to log into. This can be used to specify nicknames or abbreviations for hosts. June 26, 2007 Copyright Hemant Shah 44
45 Client recommendations LocalForward LocalForward port host:port Specifies that a TCP/IP port on the local machine be forwarded over the secure channel to the specified host and port from the remote machine. June 26, 2007 Copyright Hemant Shah 45
46 Client recommendations Port Port port_number Specifies the port number to connect on the remote host. June 26, 2007 Copyright Hemant Shah 46
47 Checking configuration To check the configuration run following command: sshd -t June 26, 2007 Copyright Hemant Shah 47
48 Key Management June 26, 2007 Copyright Hemant Shah 48
49 Key pairs ssh authenticates users using key pairs private key public key June 26, 2007 Copyright Hemant Shah 49
50 Key management commands ssh-keygen - Create key pairs ssh-agent - Holds private key in memory ssh-add - Adds key to the key agent June 26, 2007 Copyright Hemant Shah 50
51 Generating key pairs ssh-keygen -t dsa Generating public/private dsa key pair. Enter file in which to save the key (/home/shahhe/.ssh/id_dsa): Enter passphrase (empty for no passphrase): Enter same passphrase again: Your identification has been saved in /home/shahhe/.ssh/id_dsa. Your public key has been saved in /home/shahhe/.ssh/id_dsa.pub. The key fingerprint is: 99:51:ac:02:10:0c:d4:55:09:cc:86:36:cf:59:d0:33 June 26, 2007 Copyright Hemant Shah 51
52 Generating key pairs cat ~/.ssh/id_dsa -----BEGIN DSA PRIVATE KEY----- MIIBuwIBAAKBgQDPmC7jSBnJMoQ8o6/cF4GUDP/gsCqonA0UGs2g/92N8qVTxxZg U3MgZAQ96FAsaGKFDfsxoqbp1eXX7IXUS+erPOMQnDtbooLgZN3VpvStvV/hulnn HoFJoDmoE5MnrY0Su93jZe2mPp4hOrYYQu0/8r3YRFtAzz6TCauHFxO4DQIVAJYo apgvvbg8j1raefsbreoef/ixaogbajuxbydtr0wpyz5ukt11fmvs/a34st9lfzld OjR38c9sRCf8klRZ6IuqoLUZZ3jSo56+SRsraFQReCB5GLWPx5qKzHz9xi9XFseT acb3qh70ebip3uafqntvk2k8vokc4dniexz7szxzuswbimlayxf/scvl7fmlmy9d fcmf8by2aogagedk17lrld7zfwuvyjm+26zaq/qu4yhff6cfoe1lnq/1umt6sevf SZWsj9n8fj7Ez8l03gU/g+otZXDcsS6OmNMooWkADIbkHfQ6oeoK1h/3z0hV8TY4 HnOtMZuHJMf1LPFNvINbenLS+qldGvi19aTxZUkcQJiHdpr6GR3jn9cCFE9xHd8q Y8klJEyIPYK+KQ4UrbhZ -----END DSA PRIVATE KEY----- June 26, 2007 Copyright Hemant Shah 52
53 Generating key pairs cat ~/.ssh/id_dsa.pub ssh dss AAAAB3NzaC1kc3MAAACBAM+YLuNIGckyhDyjr9wXgZQM/+CwKqicDRQazaD/3Y3 ypvphfmbtcybkbd3oucxoyoun+zgipunv5dfshdrl56s84xcco1uigubk3dwm9k29x+g6we cegumgoagtkyetjrk73enl7ay+nie6thhc7t/yvdhew0dpppmjq4cxe7gnaaaafqcwkgqrl b24pcdawhn0guxjnn/4lwaaaiealrdvio1htcnlplqppxuwzvl9rfhjp0t/ov06nhfxz2xe J/ySVFnoi6qgtRlneNKjnr5JGytoVBF4IHkYtY/HmorMfP3GL1cWx5NoJvdCHvQRuI/e4AW qdo+tyry+golh00grdntjldlsxyeiytphd/+xy8vt8yuzl118ix/whlyaaacagedk17lrld 7zfWUVyJm+26ZaQ/QU4Yhff6Cfoe1lnq/1UmT6SEVfSZWsj9n8fj7Ez8l03gU/g+otZXDcs S6OmNMooWkADIbkHfQ6oeoK1h/3z0hV8TY4HnOtMZuHJMf1LPFNvINbenLS+qldGvi19aTx ZUkcQJiHdpr6GR3jn9c= June 26, 2007 Copyright Hemant Shah 53
54 Executing commands June 26, 2007 Copyright Hemant Shah 54
55 Logging into remote system ssh Last login: Mon Jun 18 21:26: from d * Problems? Questions? help@xnet.com * Type "whatsup" to see information posted to our "What's Up?" page. You have mail. You have 17 read messages. You have no new mail. /home/customer/shah {shah@typhoon} 1> June 26, 2007 Copyright Hemant Shah 55
56 Copying file to remote system scp.profile 100% KB/s 00:00 scp tmp/. profile.kubuntu 100% KB/s 00:00 June 26, 2007 Copyright Hemant Shah 56
57 Executing commands on remote system ssh ls Mail News bin mail public_html tmp June 26, 2007 Copyright Hemant Shah 57
58 Executing commands on remote system ssh -Y /opt/sfw/bin/xterm June 26, 2007 Copyright Hemant Shah 58
59 Force execution of command June 26, 2007 Copyright Hemant Shah 59
60 Force execution of command To force an execution of a command use command keyword in authorized_key2 file. command="~/bin/dumpempnames",no-port-forwarding ssh-dss AAAAB3NzaC1kc3MAAACBAIB8B1MvYlWnVeyPE6bMwrTr1OM8O2HXiQQKq9801q fmof9x3qyzzxvfegdnydtn4o1sr6t7bmcnvotc7szoglafibfqohfmiexabvyz xin/2d2juof7yu53zrx1bjhkzqqpcj6jx7fxjpqlld0bvl9r3qopipj6jt0yvy Ae4Zj9AAAAFQDoejxCMgfZ0O/Zxwxn3mFidTpogQAAAIBDQvrhRsDFhA1UUkBO 203pVujfnNYF7X58mD/WPGZ+Z4aR8dGuD21X7hC6M8ko9a9wLLYigELSkUiWps VZ/NJyBxhrCCD3YCNXeltJ7L0KaWGP96H2KkDtYsP7RMhAmztVpmlOrPzXbIpU 3jpq8dRJqUksG8mq2dbXPBWgh9xHyQAAAIBG9iwGfjPLDTH1niXk5tbZQUuEGk GZzCaBw8jJlKPXMWeE7rVmBXV5sC/zhcX3OAXUNj8OUpafxFZxbxtmnzIgnehW duwtwmiqpoi2f8ov9fculpfnywgnn4v4hmqdlscwnoie3obv05wterdyjay8bv 2Zfh9EJGEJvFFerdur/g== Key for Dumping active user names. June 26, 2007 Copyright Hemant Shah 60
61 Force execution of command Execute command as follows: ssh -i ~/keys/dumpempnames.dsa June 26, 2007 Copyright Hemant Shah 61
62 Options for authorized_keys2 file Option command="command name" environment="variable=value" from="host or ip address" no-agent-forwarding no-port-forwarding no-pty no-x11-forwarding Meaning Specify a force command Set environment variable Limit incoming hosts Disable forwarding agent Disable port forwarding Do not allocate TTY Disable X11 forwarding June 26, 2007 Copyright Hemant Shah 62
63 Port forwarding June 26, 2007 Copyright Hemant Shah 63
64 Port forwarding Client App Insecure Server App ssh client Secure ssh server June 26, 2007 Copyright Hemant Shah 64
65 Port forwarding Create SSH tunnel ssh -f -N -L10112:localhost:80 Add to ~/.ssh/config file and run ssh command Host webtunnel User shahhe Hostname LocalForward ssh -f -N webtunnel June 26, 2007 Copyright Hemant Shah 65
66 Port forwarding Start application using port on localhost firefox June 26, 2007 Copyright Hemant Shah 66
67 Agent forwarding June 26, 2007 Copyright Hemant Shah 67
68 Agent forwarding You want to login to the computer at work from your home computer or from from hotel while traveling. The computer at work is behind the firewall so you cannot connect to it directly. You are allowed to connect to a bastion host, but are not allowed to store private keys on it. What can you do? June 26, 2007 Copyright Hemant Shah 68
69 Agent Forwarding Home Bastion Work ssh sshd (proxy agent) Login ssh ssh sshd ssh June 26, 2007 Copyright Hemant Shah 69
70 sshd configuration on bastion host Port Protocol 2 PasswordAuthentication no X11Forwarding yes Compression no Subsystem sftp /usr/libexec/sftp-server June 26, 2007 Copyright Hemant Shah 70
71 ssh tunnel configuration on home system The configuration is stored in ~/.ssh/tunnel.cfg file. Host * ForwardX11 yes ForwardAgent yes NoHostAuthenticationForLocalhost yes Host bastionhost User RemoteUser IdentityFile /home/localuser/.ssh/work_dsa HostName Port June 26, 2007 Copyright Hemant Shah 71
72 ssh client configuration on home system Host * ForwardX11 yes ForwardAgent yes NoHostAuthenticationForLocalhost yes Host portmap HostName localhost LocalForward :22 LocalForward :22 Host host1 User RemoteUser IdentityFile /home/localuser/.ssh/work_dsa HostName localhost Port Host host2 User RemoteUser IdentityFile /home/localuser/.ssh/work_dsa HostName localhost Port June 26, 2007 Copyright Hemant Shah 72
73 Setting Key Pair Generate key with password Store private key on Home system Store public key on Bastion host Store public key on Work system June 26, 2007 Copyright Hemant Shah 73
74 Login into work systems Do the following on the HOME system: Start ssh-agent and add the key ssh-agent $SHELL ssh-add ~/.ssh/work_dsa Create tunnel to bastion host ssh -f -N -F ~/.ssh/tunnel.cfg bastionhost ssh -f -N Login in to work systems ssh host1 ssh host2 June 26, 2007 Copyright Hemant Shah 74
75 Environment variables June 26, 2007 Copyright Hemant Shah 75
76 Environment variables Variable Meaning Example SSH_CONNECTION Client and server socket information SSH_AUTH_SOCK Path to socket /tmp/ssh-fcrci22249/agent SSH_CLIENT Client socket information SSH_TTY Name of TTY /dev/pts/48 June 26, 2007 Copyright Hemant Shah 76
77 Other ssh based applications June 26, 2007 Copyright Hemant Shah 77
78 Other ssh based applications sshfs - ssh based file system client sftp - secure file transfer. Part of OpenSSH June 26, 2007 Copyright Hemant Shah 78
79 OpenSSH alternatives for windows PuTTY TTSSH Cygwin MSSH WinSCP FileZilla June 26, 2007 Copyright Hemant Shah 79
80 Advantages of using ssh June 26, 2007 Copyright Hemant Shah 80
81 Advantages Proven technology Strong encryption Both free and commercial versions exist Runs on many platforms Tunneling of ports works well and can be used for simple VPNs Many authentication methods supported Can be SOCKS5 proxy aware Use it instead of VPN June 26, 2007 Copyright Hemant Shah 81
82 Disadvantages of using ssh June 26, 2007 Copyright Hemant Shah 82
83 Disadvantages Port ranges & dynamic ports can't be forwarded SSH server daemon: Cannot restrict what ports may or may not be forwarded, per user When a user is authenticated by password, the client's RSA identity is not verified (against ssh_known_hosts). The verification only takes place when.[sr]hosts trust is used Port forwarding can also introduce security problems. The SSH server doesn't allow detailed configuration of what forwarding is allowed from what client to what server etc. A client on the Internet that uses SSH to access the Intranet, can expose the Intranet by port forwarding June 26, 2007 Copyright Hemant Shah 83
84 Resources Barrett, D., Silverman, R., & Byrnes, R. (2005). SSH The Definitive Guide, Second Edition. O'Reilly Media, Inc. SSH FAQ June 26, 2007 Copyright Hemant Shah 84
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