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The versions of OpenSSH and OpenSSL that ship with Ubuntu trusty are several releases out of date. How can I install updated versions?

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Here's how to install current versions of each on your computer.

First, download, build and install the latest version of LibreSSL

cd /usr/local/src (or whatever directory you like to build software in)

sudo apt-get install -y build-essential checkinstall

curl http://ftp.openbsd.org/pub/OpenBSD/LibreSSL/libressl-<version-number>.tar.gz | tar -xzv; cd libressl-<version-number>

./configure --libdir=/lib/x86_64-linux-gnu; make check; sudo checkinstall

Then build OpenSSH against the updated LibreSSL libraries

curl http://ftp3.usa.openbsd.org/pub/OpenBSD/OpenSSH/portable/openssh-<version-number>.tar.gz | tar -xzv

cd openssh-<version-number>; ./configure --libdir=/lib/x86_64-linux-gnu --with-ssl-dir=/lib/x86_64-linux-gnu

make; sudo checkinstall

Be aware that your openssh binaries will be downgraded anytime there is an 'update' to the Ubuntu openssh package, and you'll have to re-install.

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