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