OpenSSH

(SSH
(SSH -- Secure
Secure SHell)
SHell)

Silvio C. Sampaio
silviocs@fe.up.pt
Doctoral Programme in Informatics Engineering
PRODEI011 - Computer Systems Security 2009/10

Outline

Overview
Protocol details
Experiments
References

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

Overview: What is OpenSSH?

OpenSSH is a FREE version of the SSH
connectivity tools that technical users of the Internet
rely on. (SOURCE: http://www.openssh.com/)
SSH is a set of standards and associated protocols
to establish a secure channel between two
computers.
Covers authentication, encryption, and data integrity.
Originally, a replacement of insecure applications like telnet
and some others r-commands
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

Overview: History and Development

In 1995, Tatu Ylnen, a researcher at Helsinki
University of Technology, Finland, designed the first
version of the protocol (now called SSH-1)
"Secsh" was the official Internet Engineering Task
Force's (IETF) name for the IETF working group
responsible for version 2 of the SSH protocol.
In 1996, a revised version of the protocol, SSH-2, was
adopted as a standard.
This version is incompatible with SSH-1.

A complete description about the history and

development of the SSH can be found at [1].
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

Overview: SSH Features

Secure Remote Logins

Secure File Transfer and Backup
Secure Remote Command Execution
Keys and Agents
Access Control
Port Forwarding and Tunneling

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

Overview: Some SSH Implementations

Source: Daniel J. Barrett, Richard E. Silverman, and Robert G. Byrnes SSH: The Secure Shell
(The Definitive Guide), O'Reilly 2005 (2nd edition).
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

Protocol details: Introduction

The SSH protocol ensures that all communication
over the network is secure through the following
safeguards:
Encryption of data during transmission to protect privacy
Prevention of data corruption, whether deliberate or
otherwise, through integrity checking
Authentication of users and hosts to prevent unauthorized
logins/connections
Authorization or controlling access and privileges
Protection of other TCP/IP sessions through tunneling or
forwarding

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

Protocol details: Authentication Methods

Different methods can be used to authenticate users and servers
in SSH Secure Shell.
These authentication methods can be combined or used separately,
depending on the level of functionality and security you want.

Methods:
For Server authentication:

Public-Key Authentication
Certificate Authentication

For Users authentication:

Password Authentication
Public-Key Authentication
Host-Based Authentication
Certificate Authentication
Kerberos Authentication
Pluggable Authentication Module (PAM)
SecurID

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

Protocol details: Architecture

The Architecture of an general SSH System

Source: Daniel J. Barrett, Richard E. Silverman, and Robert G. Byrnes SSH: The Secure Shell
(The Definitive Guide), O'Reilly 2005 (2nd edition).
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

Protocol details: Architecture of SSH1

The Architecture of an SSH1 System

Source: Daniel J. Barrett, Richard E. Silverman, and Robert G. Byrnes SSH: The Secure Shell
(The Definitive Guide), O'Reilly 2005 (2nd edition).
PRODEI011 - Computer Systems Security 2009/10
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Protocol details: Architecture of SSH2

The Architecture of an SSH2 System

Source: Daniel J. Barrett, Richard E. Silverman, and Robert G. Byrnes SSH: The Secure Shell
(The Definitive Guide), O'Reilly 2005 (2nd edition).
PRODEI011 - Computer Systems Security 2009/10
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Protocol details: SSH1 x SSH2

SSH1 is older, slower protocol with significant
security problems
SSH2 is the newest, most efficient protocol
Resolves all known weaknesses in SSH1 security
IETF standard

SSH1 hardcodes most of its cryptography

SSH2 negotiates cryptographic algorithms at
runtime
Makes it easier to use internationally

A good summary of the difference between versions

1 and 2 of the SSH protocol can be found at:
http://www.snailbook.com/faq/ssh-1-vs-2.auto.html
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

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Protocol details: SSH1 x SSH2

The major differences between SSH-1 and
SSH-2 are, namely [1]:
Expanded algorithm negotiation between client
and server
Multiple methods for key-exchange
Certificates for public keys
More flexibility with authentication, including
partial authentication
Stronger integrity checking through cryptography
Periodic replacement of the session key
(rekeying)
PRODEI011 - Computer Systems Security 2009/10
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Protocol details: Algorithms Used

SSH-1 Ciphers
3DES

IDEA

RC4

DES

(Blowfish)

SSH1

OpenSSH

SSH-2 Ciphers
3DES

Blowfish

Twofish

CAST-128

IDEA

RC4

SSH2

F-Secure
SSH2

OpenSSH

x : The implementation supports the algorithm and is included in the default build.
o : The implementation supports the algorithm, but it isn't included in the default build
(it must be specifically enabled when compiling).
- : The implementation doesn't support the algorithm.

PRODEI011 - Computer Systems Security 2009/10

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Exp #1: Secure Remote Login (1)

Remote Login
Command line
ssh user@servidor
ssh l user servidor

Using some ssh client

At the first connection

Cliente(known_hosts) +=
Server(ssh_host_rsa_key.pub)

PRODEI011 - Computer Systems Security 2009/10

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Exp #1: Secure Remote Login (2)

X11 Forwarding
Automatic on
Linux/Unix client
ssh X user@servidor

Windows client:
XServer is needed (e.g.
Xming)
Some applications (e.g.
PuTTy) has especific
configurations (but you
can always use the
comand export
DISPLAY=Client_IP)
PRODEI011 - Computer Systems Security 2009/10
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16

Exp #2: Secure File Copy

Secure copy
Copies files between host machines
Authenticates user and host
Encrypts copied data during transmission
If keys are set up correctly for the user, no password entry will be
required for access to remote machine.
Ex: scp [[user@]host1:]file1 [] [[user@]host2:]file2
scp ssampaio@192.168.0.11:/tmp/test.txt .
scp -r ~/simulations/* ssampaio@192.168.0.11:/tmp/.
PRODEI011 - Computer Systems Security 2009/10
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Exp #3: Secure Remote Command Execution

Executes command(s) on a remote machine from a
local machine
Authenticates user and host
Encrypts transmitted data between machines
If keys are set up correctly for the user, no password
entry will be required for access to remote machine.
Ex: ssh [user@]machine command
ssh ssampaio@192.168.0.11 ls -la
PRODEI011 - Computer Systems Security 2009/10
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18

Exp #4: Port Forwarding and Tunneling

Experiment assumptions:
Servidor POP3: pop3.server.com, porta 110
Servidor SMTP: smtp.server.com, porta 25
Seu username em server.com: user
ssh -L7110:pop3.servidor.com:110 L7025:smtp.server.com:25 user@server.com
Sintaxe: -L localport:server:remoteport

In the webmail client:

Replace the POP3 pop3.servidor.com by localhost and the
port 110 by 7110
Replace the POP3 smtp.servidor.com by localhost and the
port 25 by 7025
PRODEI011 - Computer Systems Security 2009/10
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Exp #5: Automatic Authentication

Key creation
ssh-keygen -t rsa
ssh-keygen -b 1024 -t rsa

Enter file in which to save the key (/home/ac/.ssh/id_rsa):

Enter passphrase (empty for no passphrase):
Enter same passphrase again:
Just to make sure!!!: chmod 0600 ~/.ssh/id_rsa

Copying the key to remote servers

scp ~/.ssh/id_rsa.pub
remote_user@remote_host:rsa.pub_imported
ssh remote_user@remote_host
cat rsa.pub_imported >> .ssh/authorized_keys
Testing
ssh remote_user@remote_host (and i hope it works!!!)
PRODEI011 - Computer Systems Security 2009/10
Silvio C. Sampaio

20

Exp #6: File Transfer

SFTP
SFTP stands for Secure File Transfer Protocol. It provides secure file
transfer functionality over any reliable data stream. It uses SSH.
SFTP protocol runs on secure channel.
Encrypts all traffic (including passwords) to effectively.
Provides variety of authentication methods.
It can be automated by public and private key authentication.

sftp ssampaio@192.168.0.11
Once you are connected:

sftp> lcd /files [change local directory to /files]

sftp> cd /tmp [change remote directory to /etc]
sftp> get test.txt [download /tmp/test.txt to /files/test.txt]
sftp> ?
[view summary help]
sftp> bye
[terminate connection]

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

21

References
1.

2.
3.
4.

Daniel J. Barrett, Richard E. Silverman, and Robert G.

Byrnes SSH: The Secure Shell (The Definitive Guide),
O'Reilly 2005 (2nd edition).
http://www.snailbook.com/faq/ssh-1-vs-2.auto.html
http://en.wikipedia.org/wiki/Secure_Shell
http://www.openssh.org

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

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Thank you!

Any Questions?
Silvio C. Sampaio
silviocs@fe.up.pt

PRODEI011 - Computer Systems Security 2009/10

Silvio C. Sampaio

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