Passwordless SSH with encrypted homedir in Ubuntu

Quite recently I came across a very interesting issue: while configuring passwordless SSH (it's public key based, so depending on you have it configured it may not be completely passwordless) access to some of my VPS servers, I found that the same keypair just wouldn't work on one of the servers.

Not only that, but the behaviour was quite bizzare: upon my first attempt to connect the public key would get rejected and a regular password would be requested by the ssh session. But once I successfully logged in with my password, any subsequent ssh connections would happily authenticate by my public key and would let me in without a problem.

Those of you using home dir encrypiton in Ubuntu are probably smiling right now! :) But becase I have never consciously configured or used this feature, it took me a good few hours to troubleshoot the issue and come up with the fix.

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Ubuntu SSH: How To Enable Secure Shell in Ubuntu

SSH (Secure SHell) is possibly the best way to remotely access a Unix system – it's very secure thanks to automatic encryption of all the traffic, and it's also quite universal because you can do all sorts of things: access remote command line shell, forward graphics session output, establish network tunnels, set up port redirections and even transfer files over the encrypted session.

Today I'm going to show you how to get started with SSH in Ubuntu.

Installing SSH server in Ubuntu

By default, your (desktop) system will have no SSH service enabled, which means you won't be able to connect to it remotely using SSH protocol (TCP port 22). This makes installing SSH server one of the first post-install steps on your brand new Ubuntu.

The most common SSH implementation is OpenSSH. Although there are alternative implementations (closed source solutions and binary distributions maintained by various Unix and Unix-like OS vendors), OpenSSH is a de-facto standard in the secure transfers and connections industry. That's exactly what you want to install.

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