install

Additional install commands

macOS

Homebrewverified · 100%

brew install monkeysphere

local Homebrew formula metadata

Linux

Alpine Linux apkverified · 92%

sudo apk add monkeysphere

Alpine Linux edge package indexes · monkeysphere · source: dl-cdn.alpinelinux.org

Nixverified · 92%

nix profile install nixpkgs#monkeysphere

nixpkgs package indexes · pkgs/by-name/mo/monkeysphere/package.nix · source: api.github.com

overview

Package summary

Use the OpenPGP web of trust to verify ssh connections

Project links

Commands and aliases

agent-transfer
monkeysphere
monkeysphere-authentication
monkeysphere-host
openpgp2pem
openpgp2spki
openpgp2ssh
pem2openpgp

history

Project history and usage

Monkeysphere is a security tool from the OpenPGP and Debian-adjacent world that tries to bring the OpenPGP web of trust to SSH and TLS authentication. Its README frames the project as extending OpenPGP's trust model to more areas of the Internet, with an implementation that lets users keep using OpenSSH while identifying users and servers through OpenPGP keys managed by GnuPG.

Project history

The project was written by Jameson Rollins and Daniel Kahn Gillmor, according to the monkeysphere(7) manual page. Early changelog entries from 2008 show rapid work on server diagnostics, key expiration, certifier management, privilege separation, OpenSSH known_hosts and authorized_keys handling, and Debian packaging, which fits its role as a glue layer around GnuPG and OpenSSH rather than a replacement protocol.

How it is used

Administrators use Monkeysphere to bind human-readable OpenPGP user IDs to SSH keys and host identities. The tools update authorized_keys and known_hosts after checking key validity, expiration, revocation, authentication-capable subkeys, and signatures from trusted identity certifiers. That makes its package-manager niche a specialized PKI bridge for people who already trusted OpenPGP key signing and wanted that trust graph to govern SSH host verification or user login access.

Sources

security posture

Risk level: blue

broad file, network, media, or database tool signal.

Risk classifier

blue risk · medium confidence · tool

Why

broad file, network, media, or database tool signal

Signals

text:ssh

Install behavior

No Homebrew post-install hook is recorded in formula metadata.
Homebrew bottle metadata is available for 6 platform targets.
Installs with 5 runtime dependencies.
Build metadata lists 2 build dependencies.

Recommended review

Before unattended agent use, check whether the tool reads plaintext credentials, writes remote state, publishes artifacts, or shells out to plugins.

executables

Installed executables

Command	Kind	Exposure
`agent-transfer`	cli	global executable
`monkeysphere`	cli	global executable
`monkeysphere-authentication`	cli	global executable
`monkeysphere-host`	cli	global executable
`openpgp2pem`	cli	global executable
`openpgp2spki`	cli	global executable
`openpgp2ssh`	cli	global executable
`pem2openpgp`	cli	global executable

freshness

Version and freshness

These signals separate page generation age, package-manager activity, and upstream release comparison. Version lag is warned only when an evidence URL and comparable versions are present.

page generated2026-07-08

manager version0.44

manager updated2026-05-25

local dataok

upstreamnot checked

latest detectednot detected

https://tracker.debian.org/pkg/monkeysphere

infoRelease/tag comparison is only available for GitHub repositories.https://tracker.debian.org/pkg/monkeyspherenone confidence

install metadata

Package metadata

Package key	brew:monkeysphere
Version	0.44
Package manager	Homebrew
Package manager page	https://formulae.brew.sh/formula/monkeysphere
Homepage	https://tracker.debian.org/pkg/monkeysphere
Repository	https://github.com/dkg/monkeysphere
Upstream docs	https://github.com/dkg/monkeysphere#readme
License	GPL-3.0-or-later
Source archive	https://deb.debian.org/debian/pool/main/m/monkeysphere/monkeysphere_0.44.orig.tar.gz
Last updated	2026-05-25T17:02:24-04:00
Pulse	updated
Dependencies	gnupg, libassuan, libgcrypt, libgpg-error, openssl@3
Build dependencies	gnu-sed, pkgconf
Uses from macOS	perl
Bottle	available (on arm64_linux, arm64_sequoia, arm64_sonoma, arm64_tahoe, sonoma, x86_64_linux)
Homebrew post-install	not defined
Service	none declared

registry facts

Source database details

Source Database	Homebrew formula API
Tap	homebrew/core
Full Name	monkeysphere
Version Scheme	0
Revision	10
Bottle Stable Root URL	https://ghcr.io/v2/homebrew/core
Deprecated	yes
Disabled	no
Keg Only	no
URL Keys	stable

source database matches

Other package-manager records

Matches are pulled from external package-manager indexes and kept separate from local Automic Vault package links.

Nix95%

monkeysphere

nix profile install nixpkgs#monkeysphere

normalized package name match
Matched by: Monkeysphere

nixpkgs package indexes · api.github.com · nixpkgs package indexes: pkgs/by-name/mo/monkeysphere/package.nix from https://api.github.com/repos/NixOS/nixpkgs/git/trees/master?recursive=1

apk95%

monkeysphere 0.44-r4

OpenPGP web of trust certification tools for SSH and TLS servers

https://github.com/dkg/monkeysphere

sudo apk add monkeysphere

License: GPL-3.0-or-later
Architecture: x86_64
Source Package: monkeysphere
1 dependencies
1 provides
normalized package name match
Matched by: Monkeysphere

Alpine Linux edge package indexes · dl-cdn.alpinelinux.org · Alpine Linux edge package indexes: monkeysphere from https://dl-cdn.alpinelinux.org/alpine/edge/community/x86_64/APKINDEX.tar.gz

apk95%

monkeysphere-doc 0.44-r4

OpenPGP web of trust certification tools for SSH and TLS servers (documentation)

https://github.com/dkg/monkeysphere

sudo apk add monkeysphere-doc

License: GPL-3.0-or-later
Architecture: x86_64
Source Package: monkeysphere
normalized package name match
Matched by: Monkeysphere

Alpine Linux edge package indexes · dl-cdn.alpinelinux.org · Alpine Linux edge package indexes: monkeysphere-doc from https://dl-cdn.alpinelinux.org/alpine/edge/community/x86_64/APKINDEX.tar.gz

package graph

Links come from deterministic package relationships, av.db category and tag curation, ecosystem matches, and package hub membership.

source trail

Generated from repository data

This page is generated by av-web from the private package SQLite artifact built by scripts/generate-pkg-sqlite.py.

Combined YAML source

View the package source record on GitHub.

combined/monkeysphere.yml

Used sources

Geiger risk classifier
Nucleus package database
av.db category and tag curation
cross-ecosystem install command graph
curated package history
external package-manager database matches
package relationship graph
package version freshness
package-page enrichment

Install monkeysphere with Homebrew, apk, Nix