Ahhh, the joys of a IT departments that think everybody just uses Word/Excel/Outlook and just browses to Facebook at lunchtime.
Networks that transparently proxy HTTP/HTTPS (probably with man in the middle TLS CA certs deployed to all the machines, but that is an entirely different problem) and block everything else really do not work in the modern world where access to places like GitHub via SSH or devices connecting out via MQTT are needed.
One possible solution to the SSH problem is a bastion host. This is a machine that can be reached from the internal network but is also allowed to connect to the outside world. This allows you to use this machine as a jumping off point to reach services blocked by the firewall.
The simple way is to log into the bastion, and then from the shell connect on to your intended external host, this works for targets you want a shell on but not for things like cloning/updating git repositories. We also want to automate as much of this as possible.
The first step is to set up public/private key login for the bastion machine. To do this we first generate a key pair with the
$ ssh-keygen -f ~/.ssh/bastion -t ecdsa -b 521 Generating public/private ecdsa key pair. Enter passphrase (empty for no passphrase): Enter same passphrase again: Your identification has been saved in ~/.ssh/bastion. Your public key has been saved in ~/.ssh/bastion.pub. The key fingerprint is: SHA256:3Cfr60QRNbkRHDt6LEUUcemhKFmonqDlgEETgZl+H8A hardillb@tiefighter The key's randomart image is: +---[ECDSA 521]---+ |oB+ ..+X*.. | |= .E . .o++o | |.o . . o..+= . | |....o...o..=o.. | | .=.o..S.* + | | . ..o . * | | o | | o | | .+. | +----[SHA256]-----+
In this case we want to leave the passphrase blank because we want to use this key as part of automation of other steps, normally you should use a passphrase to protect access should the keys be compromised.
Once generated you can copy it to the `~/.ssh/authorized_keys` file on the bastion machine using the
$ ssh-copy-id -i ~/.ssh/bastion user@bastion
Once that is in place we should be able to use the key to log straight into the bastion machine. We can now use the `-J` option to specify the bastion as a jump point to reach a remote machine.
$ ssh -J user@bastion firstname.lastname@example.org
We can also add this as an entry in the `.ssh/config` file which is more useful for things like git where it’s harder to get at the actual ssh command line.
Host bastion HostName bastion User user IdentityFile ~/.ssh/bastion Host github Hostname github.com User git IdentityFile ~/.ssh/github ProxyCommand ssh -W %h:%p bastion
This config will proxy all git commands working with remote repositories on github.com via the bastion machine, using the
bastion key to authenticate with the bastion machine and the
github key to authenticate with github. This is all totally transparent to git.
ssh also supports a bunch of other useful ticks, such as port forwarding from either end of the connection.
It also can proxy other protocols using the Socks tunnelling protocol which means it can be used as poor man’s VPN in some situations. To enable Socks proxying you can use
-D option to give a local port number or the
DynamixProxy directive in the
~/.ssh/config file. This option is really useful with web browser that supports Socks proxies as it means you can point the browser at a local port and have it surf the web as if it was the remote machine.
All of this still works if you are using a bastion machine.
Combining all this really useful SSH capability with a the Raspberry Pi gadgets makes it possible to carry a bastion host with you. Using a Raspberry Pi Zero W or even a full sized Pi 4 that can be configured to join a more open WiFi network (e.g. a visitor or testing network) you can have a device you just plug into a spare USB port that will give you a jumping off point to the outside world while still being connected to the more restricted internal network with all that provides. Just don’t tell IT security ;-).
This works well because even the most locked down machine normally still allows USB network adapters to be used.