In this video I show you How to Migrate from OpenSSL to LibreSSL on Gentoo Linux. LibreSSL is a version of the TLS/crypto stack forked from OpenSSL in 2014, with goals of modernizing the codebase, improving security, and applying best practice development processes. LibreSSL is considered by most people to be a better implementation of SSL compared to OpenSSL as it has a smaller codebase, and is not vulnerable to as many exploits as the OpenSSL library, one example is heartbleed which was a big vulnerability found in openssl that exploits a weakness in legacy code found in openssl but not Libressl, This weakness allows stealing the information protected, under normal conditions, by the SSL/TLS encryption used to secure the Internet.

Steps to migrate listed below that I covered in the video (easier to copy and paste)

emerge -uvNDq world emerge gentoolkit

add libressl to your USE variable in /etc/portage/make.conf add CURL_SSL="libressl" to the bottom of /etc/portage/make.conf

mkdir /etc/portage/profile

*(Replace to with double greater than symbol)

echo "-libressl" to /etc/portage/profile/use.stable.mask

echo "dev-libs/openssl" to /etc/portage/package.mask

echo "dev-libs/libressl" to /etc/portage/package.accept_keywords

emerge -f libressl

emerge -C openssl emerge -1q libressl

emerge -1q openssh wget python:2.7 python:3.6 iputils

emerge -q @preserved-rebuild

then unmount and reboot following the typical procedure

exit cd umount -l /mnt/gentoo/dev{/shm,/pts,} umount -R /mnt/gentoo reboot

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