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SSH / SSL 
Kaustubh Joshi 
September 15, 2014 1
 One of the primary goals of the ARPANET was remote 
access 
 Several different connections allowed 
 rlogin 
 rcp 
 rsh 
 All data was unencrypted 
 This was a different world than exists today. 
2 
Secure Shell 
September 15, 2014
 SSH is a UNIX-based command interface and 
protocol for securely accessing a remote computer 
 Suite of four utilities—slogin, ssh, sftp, and scp 
 Can protect against: 
 IP spoofing 
 DNS spoofing 
 Intercepting information 
 Sniffing 
 Tunneling 
3 
Secure Shell 
Contd. 
September 15, 2014
SSH 
Objectives 
 Protect data sent over the network 
 Negotiate an encryption algorithm between sender 
and receiver 
 Use that algorithm and a session key to encrypt / 
decrypt data sent 
 Provide site authentication 
 Use public key / fingerprint to ensure identity of 
remote host. 
 Relies on locally generated keys, so no certifying 
authority is generally available. 
September 15, 2014 4
SSH 
supported 
Graphical 
FTP Client 
https://filezilla-project.org/download.php?type=client 
September 15, 2014 5
Installation 
of SSL 
manually 
from 
terminal 
 Install mod_ssl 
 yum install mod ssl 
 Create an SSL Certificate 
 # cd /etc/pki/tls/certs 
# openssl genrsa -des3 -out apachekey.pem 2048 
 Generate a Certificate Signing Request (CSR) 
 # openssl req -new -key apachekey.pem -out 
apachekey.csr 
 Create the Web Server Certificate 
 # openssl ca -in apachekey.csr -out apachecert.pem 
September 15, 2014 6
Installation 
 Install SSL Certificate 
 # cp apachecert.pem /etc/pki/tls/http/ 
# cp apachekey.pem /etc/pki/tls/http/ 
 # vi /etc/httpd/conf.d/ssl.conf 
 Listen 10.10.29.68:443 
 SSLRandomSeed startup file:/dev/urandom 1024 
 SSLRandomSeed connect file:/dev/urandom 1024 
 <VirtualHost www.nixcraft.com:443> 
SSLEngine On 
SSLCertificateFile /etc/pki/tls/http/apachecert.pem 
SSLCertificateKeyFile /etc/pki/tls/http/apachekey.pem 
SSLProtocolAll -SSLv2 
SSLCipherSuite HIGH:MEDIUM:!aNULL:+MD5 
DocumentRoot "/var/www/html/ssl" 
ServerName www.nixcraft.com:443 
</VirtualHost> 
 # mkdir -p /var/www/html/ssl 
 # vi /etc/httpd/conf/httpd.conf 
 <Directory /var/www/html/ssl> 
SSLRequireSSL 
SSLOptions +StrictRequire 
SSLRequire %{HTTP_HOST} eq "www.nixcraft.com" 
ErrorDocument 403 
https://www.nixcraft.com/sslerror.html 
</Directory> 
 September 15, 2014 # service httpd restart 7
Installation 
 Firewall Configuration 
 /etc/sysconfig/iptables 
 -A RH-Firewall-1-INPUT -m state --state NEW -p tcp 
--dport 443 -j ACCEPT 
 # service iptables restart 
September 15, 2014 8
SSL in demoroot – vmware guestOS 
September 15, 2014 9
10 
SSH Client SSH Server 
SSH2? 
SSH2 
Diffie-Helman, etc? 
Diffie-Helman 
SSL secure Send Serv_Pub_Key 
communication 
Serv_Pub_key(S_key) 
OK 
S_key(Uname,pwd) 
OK 
S_key(data) 
September 15, 2014
11 
SSH 
Wireshark 
Trace 
September 15, 2014
Problems with Password Authentication 
Passwords can be guessed. 
Default allows multiple attempts against account 
 Only 1 account / password needs to be guessed 
 Alternate approach is to use public / private keys 
to authenticate user 
Public Key Authentication 
 Create public / private keypair 
Ensure that private 
Upload public key to server user account: 
~.ssh/authorized_keys 
 ssh –o PreferredAuthentications=publickey 
server.example.org 
SSH 
Communications 
using public 
key 
September 15, 2014
SSH Client SSH Server 
SSH2? 
SSH2 
Diffie-Helman, etc? 
Diffie-Helman 
Serv_Pub_key(S_key) 
OK 
S_key(Uname) 
OK 
S_key(data) 
Send Serv_Pub_Key 
Client_Pub_key(Random) 
Client_Pri_key(msg) 
Hash(Random) 
SSH 
Communications 
using public 
key 
September 15, 2014
sFTP in Linux 
September 15, 2014 14
sFTP in Linux 
(contd.) 
September 15, 2014 15
sFTP in Linux 
(contd.) 
September 15, 2014 16
SSH 
Tunneling 
 Use SSH to create an encrypted channel between remote 
host and server 
 Use that encrypted channel to carry other traffic. 
September 15, 2014 17
SSH 
Tunneling 
ssh –L 12345:192.168.1.10:80 –l root homenet.net 
September 15, 2014
SSL/TLS 
Security 
 Depends on integrity of public key certificate 
 Public Key Infrastructure (PKI) 
 Components necessary to securely distribute public 
keys 
 Certificate Authorities: Organizations that certify 
the relationship between a public key and its owner. 
 Verisign,Thawte 
September 15, 2014 19
SSL/TLS 
Vulnerability 
SSL/TLS supports the concept of session 
renegotiation due to errors, requests, 
etc. 
This feature assumes that the 
renegotiation is with the original party, 
and any requests or messages 
transmitted before the renegotiation are 
combined (pre-pended) with the 
requests after renegotiation 
This behavior can be abused to allow 
man-in-the-middle attacks 
Demonstrated with https, but the 
vulnerability exists with any application 
that uses SSL/TLS 
September 15, 2014
Reference 
 sce.umkc.edu/~cotterr/it426_sp13/CS490ns_SSH_SSL_sp11_ 
bw.ppt 
 http://www.cyberciti.biz/faq/rhel-apache-httpd-mod-ssl-tutorial/ 
SSH 
 SSH Tutorial 
(http://www.suso.org/docs/shell/ssh.sdf) 
 www.openssh.org 
 UNIX Secure Shell – Carasik – McGraw-Hill, 1999 
 SSH Agent Forwarding 
(unixwiz.net/techtips/ssh-agent-forwarding.html) 
SSL 
 www.openSSL.org 
 RFCs – 2246, 3546 
 SSL Authentication Gap (SSL Gap) 
(http://www.phonefactor.com/sslgap ) 
 TLS/SSL renegotiation vulnerability explained 
(http://www.g-sec.lu/practicaltls.pdf ) 
September 15, 2014 21

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Ost ssl lec

  • 1. SSH / SSL Kaustubh Joshi September 15, 2014 1
  • 2.  One of the primary goals of the ARPANET was remote access  Several different connections allowed  rlogin  rcp  rsh  All data was unencrypted  This was a different world than exists today. 2 Secure Shell September 15, 2014
  • 3.  SSH is a UNIX-based command interface and protocol for securely accessing a remote computer  Suite of four utilities—slogin, ssh, sftp, and scp  Can protect against:  IP spoofing  DNS spoofing  Intercepting information  Sniffing  Tunneling 3 Secure Shell Contd. September 15, 2014
  • 4. SSH Objectives  Protect data sent over the network  Negotiate an encryption algorithm between sender and receiver  Use that algorithm and a session key to encrypt / decrypt data sent  Provide site authentication  Use public key / fingerprint to ensure identity of remote host.  Relies on locally generated keys, so no certifying authority is generally available. September 15, 2014 4
  • 5. SSH supported Graphical FTP Client https://filezilla-project.org/download.php?type=client September 15, 2014 5
  • 6. Installation of SSL manually from terminal  Install mod_ssl  yum install mod ssl  Create an SSL Certificate  # cd /etc/pki/tls/certs # openssl genrsa -des3 -out apachekey.pem 2048  Generate a Certificate Signing Request (CSR)  # openssl req -new -key apachekey.pem -out apachekey.csr  Create the Web Server Certificate  # openssl ca -in apachekey.csr -out apachecert.pem September 15, 2014 6
  • 7. Installation  Install SSL Certificate  # cp apachecert.pem /etc/pki/tls/http/ # cp apachekey.pem /etc/pki/tls/http/  # vi /etc/httpd/conf.d/ssl.conf  Listen 10.10.29.68:443  SSLRandomSeed startup file:/dev/urandom 1024  SSLRandomSeed connect file:/dev/urandom 1024  <VirtualHost www.nixcraft.com:443> SSLEngine On SSLCertificateFile /etc/pki/tls/http/apachecert.pem SSLCertificateKeyFile /etc/pki/tls/http/apachekey.pem SSLProtocolAll -SSLv2 SSLCipherSuite HIGH:MEDIUM:!aNULL:+MD5 DocumentRoot "/var/www/html/ssl" ServerName www.nixcraft.com:443 </VirtualHost>  # mkdir -p /var/www/html/ssl  # vi /etc/httpd/conf/httpd.conf  <Directory /var/www/html/ssl> SSLRequireSSL SSLOptions +StrictRequire SSLRequire %{HTTP_HOST} eq "www.nixcraft.com" ErrorDocument 403 https://www.nixcraft.com/sslerror.html </Directory>  September 15, 2014 # service httpd restart 7
  • 8. Installation  Firewall Configuration  /etc/sysconfig/iptables  -A RH-Firewall-1-INPUT -m state --state NEW -p tcp --dport 443 -j ACCEPT  # service iptables restart September 15, 2014 8
  • 9. SSL in demoroot – vmware guestOS September 15, 2014 9
  • 10. 10 SSH Client SSH Server SSH2? SSH2 Diffie-Helman, etc? Diffie-Helman SSL secure Send Serv_Pub_Key communication Serv_Pub_key(S_key) OK S_key(Uname,pwd) OK S_key(data) September 15, 2014
  • 11. 11 SSH Wireshark Trace September 15, 2014
  • 12. Problems with Password Authentication Passwords can be guessed. Default allows multiple attempts against account  Only 1 account / password needs to be guessed  Alternate approach is to use public / private keys to authenticate user Public Key Authentication  Create public / private keypair Ensure that private Upload public key to server user account: ~.ssh/authorized_keys  ssh –o PreferredAuthentications=publickey server.example.org SSH Communications using public key September 15, 2014
  • 13. SSH Client SSH Server SSH2? SSH2 Diffie-Helman, etc? Diffie-Helman Serv_Pub_key(S_key) OK S_key(Uname) OK S_key(data) Send Serv_Pub_Key Client_Pub_key(Random) Client_Pri_key(msg) Hash(Random) SSH Communications using public key September 15, 2014
  • 14. sFTP in Linux September 15, 2014 14
  • 15. sFTP in Linux (contd.) September 15, 2014 15
  • 16. sFTP in Linux (contd.) September 15, 2014 16
  • 17. SSH Tunneling  Use SSH to create an encrypted channel between remote host and server  Use that encrypted channel to carry other traffic. September 15, 2014 17
  • 18. SSH Tunneling ssh –L 12345:192.168.1.10:80 –l root homenet.net September 15, 2014
  • 19. SSL/TLS Security  Depends on integrity of public key certificate  Public Key Infrastructure (PKI)  Components necessary to securely distribute public keys  Certificate Authorities: Organizations that certify the relationship between a public key and its owner.  Verisign,Thawte September 15, 2014 19
  • 20. SSL/TLS Vulnerability SSL/TLS supports the concept of session renegotiation due to errors, requests, etc. This feature assumes that the renegotiation is with the original party, and any requests or messages transmitted before the renegotiation are combined (pre-pended) with the requests after renegotiation This behavior can be abused to allow man-in-the-middle attacks Demonstrated with https, but the vulnerability exists with any application that uses SSL/TLS September 15, 2014
  • 21. Reference  sce.umkc.edu/~cotterr/it426_sp13/CS490ns_SSH_SSL_sp11_ bw.ppt  http://www.cyberciti.biz/faq/rhel-apache-httpd-mod-ssl-tutorial/ SSH  SSH Tutorial (http://www.suso.org/docs/shell/ssh.sdf)  www.openssh.org  UNIX Secure Shell – Carasik – McGraw-Hill, 1999  SSH Agent Forwarding (unixwiz.net/techtips/ssh-agent-forwarding.html) SSL  www.openSSL.org  RFCs – 2246, 3546  SSL Authentication Gap (SSL Gap) (http://www.phonefactor.com/sslgap )  TLS/SSL renegotiation vulnerability explained (http://www.g-sec.lu/practicaltls.pdf ) September 15, 2014 21