Upgrade OpenSSH Server on Debian Jessie to Latest Version

debian-jessiessh

I have a Debian 8 server for a customer that is failing a PCI scan, presumably running:
nmap -p 22 -sV customer.edu

which returns

22/tcp open ssh OpenSSH 6.7p1 Debian 5+deb8u7

This should be easy, given my /etc/apt/sources.list is this:

deb http://mirror.rackspace.com/debian jessie main
deb-src http://mirror.rackspace.com/debian jessie main
deb http://mirror.rackspace.com/debian-security/ jessie/updates main
deb-src http://mirror.rackspace.com/debian-security/ jessie/updates main
deb http://packages.dotdeb.org jessie all
deb-src http://packages.dotdeb.org jessie all
deb http://ftp.us.debian.org/debian/ jessie main contrib non-free
deb-src http://ftp.us.debian.org/debian/ jessie main contrib non-free
deb http://ftp.debian.org/debian jessie-backports main
deb http://security.debian.org/ jessie/updates main contrib non-free

sudo apt-get upgrade openssh-server returns:

Calculating upgrade... openssh-server is already the newest version.

Is there a better way to get the latest OpenSSH server?

I attempted to download it, install its OpenSSL 1.0.2-stable dependency in /usr/local/ but having serious troubles with it failing.

Are my choices to find a better source in apt-get, or attempt to install it and its OpenSSL dependency in /usr/local and manually point systemctl to those binaries?

Best Answer

failing a PCI scan

Document for your auditor the version of the package installed. Reference security updates regarding OpenSSH, in this case from Debian. Possibly cross reference relevant CVEs.

Parsing a version number is fragile. Stable distros generally do not upgrade the version, but apply their own patches.

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