jmenbo/upgrade_openssh_on_os_10.9.x.md

## upgrade_openssh_on_os_10.9.x.md

      
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              upgrade_openssh_on_os_10.9.x.md
            
          
    Manually upgrade OpenSSH on OS 10.9.x

NOTE: Installation and testing was done on a clean Mavericks (OS 10.9) installation

Install Brew:

Install Homebrew prereqs:
xcode-select --install

Install Homebrew
ruby -e "$(curl -fsSL https://raw.githubusercontent.com/Homebrew/install/master/install)"

Enable Brew to override OSX system binaries
brew tap homebrew/dupes

Upgrade OpenSSL which is required for OpenSSH

brew install openssl

Upgrade OpenSSH

brew install openssh --with-brewed-openssl --with-keychain-support

Change default ssh-agent used by system

Make a backup of original plist file:
sudo cp /System/Library/LaunchAgents/org.openbsd.ssh-agent.plist Desktop/

Edit the plist file:
sudo vim /System/Library/LaunchAgents/org.openbsd.ssh-agent.plist 

Replace the following two lines:
<string>/usr/bin/ssh-agent</string>
        <string>-l</string>

With this:
<string>/usr/local/bin/ssh-agent</string>
        <string>-D</string>

NOTE the dash before the D -D

Update the system to see the changes to the plist file:
launchctl unload /System/Library/LaunchAgents/org.openbsd.ssh-agent.plist 
launchctl load -w /System/Library/LaunchAgents/org.openbsd.ssh-agent.plist 
launchctl start org.openbsd.ssh-agent
launchctl list | grep org.openbsd.ssh

Replace the ssh system binary with a symlink to the new Brew'ed ssh binary

Backup the original binary:
sudo mv /usr/bin/ssh Desktop/

Create the symlink:
sudo ln -s /usr/local/bin/ssh /usr/bin/ssh

Add the following snipped to all users .bash_profile file
eval $(ssh-agent)
    function cleanup {
        echo \"Killing SSH-Agent\"
        kill -9 $SSH_AGENT_PID
    }
trap cleanup EXIT
Reboot the system:
sudo shutdown -r now

Check that system is using the new SSH version
ssh -V

Remove homebrew dupes

brew untap homebrew/dupes

REFERENCES:

http://brew.sh/
https://github.com/Homebrew/homebrew/blob/master/share/doc/homebrew/Installation.md
https://mochtu.de/2015/01/07/updating-openssh-on-mac-os-x-10-10-yosemite/
https://coderwall.com/p/qdwcpg/using-the-latest-ssh-from-homebrew-on-osx
http://www.dctrwatson.com/2013/07/how-to-update-openssh-on-mac-os-x/
http://blog.macromates.com/2006/keychain-access-from-shell/
http://www.lifeofguenter.de/2015/01/compile-openssh-67-with-libressl-on-osx.html
https://developer.apple.com/library/mac/documentation/Darwin/Reference/ManPages/man1/security.1.html
https://github.com/torsten/keychain_access