Ansible FreeBSD Jail Connection Plugin

An Ansible connection plugin that runs tasks inside a FreeBSD jail by SSH-ing to the jail host and wrapping every command in jexec. You do not need direct SSH access to the jail itself: the jail needs no sshd, no Python-over-SSH setup, no network address of its own.

The plugin inherits from Ansible's built-in ssh connection plugin, so every SSH option (control persist, jump hosts, key files, custom ports, etc.) works unchanged.

Features

• Inherits the full SSH plugin: options are merged from the live ssh plugin at import time, so the plugin stays in sync with whichever ansible-core is installed.
• Everything happens inside the jail: commands and file transfers run through jexec, confined to the jail's chroot. A symlink planted inside a jail can never redirect a privileged write or read onto a host path.
• Safe by construction: jail names are validated, paths are traversal-checked and normalized, and every shell argument is shlex.quoted.
• Minimal host footprint: the SSH user needs a doas/sudo rule for exactly one command: jexec.
• Zero extra round trips for exec-only workloads: no probing at connect time; put_file costs two extra execs (private staging directory, then the in-jail write).
• doas, sudo, or none for host-side privilege escalation around jexec.

Demo

Executing Ansible tasks inside FreeBSD jails through the jailexec connection plugin.

How it works

For every task, the plugin opens a normal SSH session to the jail host (reusing ControlPersist connections like the stock ssh plugin) and runs:

doas jexec [-U <jail_user>] <jail_name> /bin/sh -c '<command>'

File transfers stage through the host and complete inside the jail:

• put_file: create a private (0700) staging directory /tmp/ansible-jailexec-<hex> on the host, upload into it (SFTP, SCP or piped, per ssh_transfer_method), then doas jexec <jail> /bin/sh -c 'mkdir -p <dir> && cat > <dest>' < <staged> and remove the directory; the write resolves entirely within the jail's filesystem namespace.
• fetch_file: create the private staging directory and run doas jexec <jail> /bin/sh -c 'cat < <src>' > <staged> in one round trip, then download the staged copy and remove the directory.

Requirements

• Control machine: Python 3.9+, ansible-core >= 2.14
• Jail host: FreeBSD with jexec available, and doas or sudo configured for the SSH user (not needed if you SSH in as root, see ansible_jail_privilege_escalation=none)
• Jails: must be running, with /bin/sh and cat available (both ship in the FreeBSD base system), plus Python for Ansible modules as usual

Installation

As a user plugin

curl -O https://raw.githubusercontent.com/chofstede/ansible_jailexec/main/jailexec.py
mkdir -p ~/.ansible/plugins/connection/
mv jailexec.py ~/.ansible/plugins/connection/

As a project plugin

mkdir -p connection_plugins/
curl -o connection_plugins/jailexec.py \
     https://raw.githubusercontent.com/chofstede/ansible_jailexec/main/jailexec.py

Then point Ansible at it from ansible.cfg:

[defaults]
connection_plugins = ./connection_plugins

Via pip

pip install ansible-jailexec

(Installs jailexec.py as a top-level module; Ansible's plugin loader will still need it under a connection_plugins/ path, or set ANSIBLE_CONNECTION_PLUGINS to the install location.)

Quick start

1. Inventory

[freebsd_jails]
web-jail  ansible_connection=jailexec  ansible_jail_host=jail-host.example.com
db-jail   ansible_connection=jailexec  ansible_jail_host=jail-host.example.com  ansible_jail_user=postgres
app-jail  ansible_connection=jailexec  ansible_jail_host=jail-host.example.com  ansible_ssh_port=30822

The inventory hostname (web-jail, db-jail, ...) doubles as the jail name unless you override it with ansible_jail_name. Tasks with delegate_to run in the delegated host's jail (or in its ansible_jail_name). Setting ansible_host does not affect the jail name; it is an SSH-level alias for the jail host's address, like ansible_jail_host.

2. Ping

ansible -i hosts.ini freebsd_jails -m ping

Expected:

web-jail | SUCCESS => {
    "changed": false,
    "ping": "pong"
}

3. Run tasks

ansible -i hosts.ini freebsd_jails -m ansible.builtin.command -a "uname -a"
ansible -i hosts.ini freebsd_jails -m community.general.pkgng -a "name=nginx state=present"

Configuration reference

Plugin-specific options

Variable	Required	Default	Description
ansible_jail_host	✅	(none)	Hostname or IP of the FreeBSD host that runs the jail.
ansible_jail_name		inventory hostname	Override the jail name if it differs from the inventory hostname.
ansible_jail_user		root	User to run commands (and file transfers) as inside the jail, resolved against the jail's password database (jexec -U).
ansible_jail_privilege_escalation		doas	Host-side privilege escalation for jexec. One of doas, sudo, none. Use none when you already SSH to the host as root and have no doas/sudo.
ansible_jail_root		(none)	Deprecated, ignored since 2.0.0. Transfers run inside the jail via jexec, so the jail's on-host path is no longer needed. Setting it only produces a warning.

SSH options

The plugin inherits every option of the built-in ssh connection plugin: ansible_ssh_port, ansible_ssh_private_key_file, ansible_ssh_common_args, ansible_ssh_extra_args, ControlPersist, jump hosts, and so on.

For the full list, see:

ansible-doc -t connection ssh

Privilege escalation: two independent layers

There are two places where privileges can be escalated, and it's easy to conflate them:

1. ansible_jail_privilege_escalation (this plugin) runs jexec on the host as root so the plugin can enter the jail. Default: doas. Set it to none when the SSH user is already root on the host (so no doas/sudo is installed); the plugin then invokes jexec directly.
2. Ansible become (become: yes, --become, ansible_become_method) runs the task payload inside the jail under a different user. Use this if ansible_jail_user is non-root and the task needs root inside the jail.

Typical setup: leave ansible_jail_user=root (the default) and skip become entirely; the plugin's own privilege escalation is already enough.

Note that with a non-root ansible_jail_user, file transfers also run as that user inside the jail; copying to root-owned locations then requires become, exactly as it would over plain SSH.

FreeBSD host setup

The SSH user needs to run exactly one command as root: jexec.

Add it to doas:

# /usr/local/etc/doas.conf
permit nopass ansible as root cmd jexec

or to sudoers (edit with visudo):

ansible ALL=(root) NOPASSWD: /usr/sbin/jexec

Upgrading from 1.x? The jls, mkdir, mv, and rm rules that earlier versions needed are no longer used and can be removed.

Playbook example

---
- name: Configure FreeBSD jails
  hosts: freebsd_jails
  gather_facts: true
  tasks:
    - name: Install nginx
      community.general.pkgng:
        name: nginx
        state: present

    - name: Ship configuration
      ansible.builtin.copy:
        src: nginx.conf
        dest: /usr/local/etc/nginx/nginx.conf
        backup: true
      notify: restart nginx

    - name: Enable and start nginx
      ansible.builtin.service:
        name: nginx
        state: started
        enabled: true

  handlers:
    - name: restart nginx
      ansible.builtin.service:
        name: nginx
        state: restarted

Upgrading from 1.x

Version 2.0.0 moves all file transfers inside the jail (see Security considerations and the CHANGELOG). For typical setups (ansible_jail_user=root) no inventory change is needed. Things to check:

• doas/sudoers can be trimmed to the single jexec rule shown above.
• ansible_jail_root is ignored (with a warning). Simply remove it; the path-mapping problem it worked around no longer exists.
• ansible_jail_user is now resolved in the jail's password database (jexec -U), as the documentation always promised. If you depended on the host's password database (jexec -u semantics), align the user accounts or use become.
• Transfers run as ansible_jail_user, no longer silently as root. Non-root jail users writing to root-owned paths need become: yes.

Troubleshooting

Enable verbose mode:

ansible -vvv -i hosts.ini freebsd_jails -m ping

Plugin log lines are prefixed with jailexec::

jailexec: exec [web-jail]: /bin/sh -c 'echo hi'
jailexec: put_file /local/nginx.conf -> jail:/usr/local/etc/nginx/nginx.conf
jailexec: fetch_file jail:/var/log/nginx/access.log -> /tmp/access.log

Common error messages

Message	Cause	Fix
ansible_jail_host is not set for jail 'X'	Missing inventory variable.	Add ansible_jail_host=<host> to inventory.
jexec: jail "X" not found (in task stderr)	The jail isn't running, or the name is wrong.	jls on the host; service jail onestart X; check ansible_jail_name.
doas: not found / sudo: not found (exit 127)	No privilege-escalation helper on the host.	Install/configure doas, or set ansible_jail_privilege_escalation=none when SSH-ing in as root.
doas: Operation not permitted / sudo: a password is required	The SSH user has no (passwordless) rule for jexec.	Add the doas.conf/sudoers rule shown above.
Invalid jail name 'X': ...	Jail name contains shell-unsafe characters or starts with -/..	Rename, or use ansible_jail_name to override.
Path contains '..' traversal: X	A module tried to put_file/fetch_file with .. in the path.	Use absolute paths without .. segments.
put_file to jail:X failed: ...	Writing inside the jail failed (permissions, read-only filesystem, full disk).	Check the path and ansible_jail_user's rights inside the jail; use become for root-owned paths.
fetch_file from jail:X failed: ...	Reading inside the jail failed (missing file, permissions).	Verify the path exists and is readable by ansible_jail_user.
ansible_jail_root is deprecated and ignored (warning)	Leftover 1.x inventory variable.	Remove ansible_jail_root; it is no longer needed.
Failed to create temporary directory with ~<ssh-user> in the failing command	Ansible builds its temp path from the SSH user's home directory, but that user usually does not exist inside the jail — and a non-root ansible_jail_user cannot write to the jail's /.	Set ansible_remote_tmp=/tmp/.ansible-tmp (or any jail-writable path) for your jail hosts.

Security considerations

• Transfers are confined to the jail: put_file and fetch_file execute mkdir/cat inside the jail via jexec, so all path resolution happens within the jail's chroot. A symlink planted inside a (potentially compromised) jail cannot redirect a privileged write or read to a host path. (Versions before 2.0.0 performed root-owned mv operations on host-side paths and were vulnerable to exactly that; upgrade.)
• Input validation: jail names are matched against ^[A-Za-z0-9_][A-Za-z0-9._-]*$ and length-capped at 255. Paths are rejected if any component is .., and are normalized to absolute in-jail paths.
• Shell safety: every argument crossing the SSH wire is shlex.quoted; the user-supplied command is the final argument to /bin/sh -c and is not further interpreted by the plugin. Fetched files are read with cat < file redirection, ruling out option injection.
• File staging: transfers stage on the host inside a per-transfer directory /tmp/ansible-jailexec-<hex> (96 bits of randomness) created with mode 0700, so other host users cannot read the payload in transit regardless of the source file's mode or the transfer method. mkdir refuses a pre-existing name, and the directory is removed even when the transfer fails. (Versions up to 2.0.2 uploaded put_file payloads as bare, often world-readable files in /tmp; upgrade.)
• Minimal escalation surface: the only command the SSH user runs via doas/sudo is jexec.
• No new network ports: everything rides the existing SSH connection, including control-persist reuse.
• Internal plumbing never engages become: plugin-internal commands run with sudoable=False, so they neither wait for become prompts nor allocate pseudo-terminals.

Development

# Install test dependencies
pip install -r requirements-test.txt

# Run the test suite with coverage (gate: 100%)
pytest

# Format / lint / security scan (same as CI)
black jailexec.py tests/
isort jailexec.py tests/
flake8 jailexec.py --max-line-length=100 --extend-ignore=E203,W503
bandit -r jailexec.py

See tests/integration/README.md for end-to-end tests against a real FreeBSD host.

License

BSD 2-Clause, see LICENSE.

Support

• Issues: https://github.com/chofstede/ansible_jailexec/issues
• Changelog: CHANGELOG.md