macOS
Homebrewverified · 100%
brew install monkeyspherelocal Homebrew formula metadata
brew / rank 6437
Install monkeysphere with Homebrew, apk, Nix
Use the OpenPGP web of trust to verify ssh connections. Version 0.44 via Homebrew; verified 2026-05-25. Also installable with nix: nix profile install nixpkgs#monkeysphere.
install
Additional install commands
Linux
Alpine Linux apkverified · 92%
sudo apk add monkeysphereAlpine Linux edge package indexes · monkeysphere · source: dl-cdn.alpinelinux.org
Nixverified · 92%
nix profile install nixpkgs#monkeyspherenixpkgs 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 bottle metadata was recorded.
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 | Note |
|---|---|---|---|
agent-transfer | executable | indexed executable | Discovered from the local executable index. |
monkeysphere | executable | indexed executable | Discovered from the local executable index. |
monkeysphere-authentication | executable | indexed executable | Discovered from the local executable index. |
monkeysphere-host | executable | indexed executable | Discovered from the local executable index. |
openpgp2pem | executable | indexed executable | Discovered from the local executable index. |
openpgp2spki | executable | indexed executable | Discovered from the local executable index. |
openpgp2ssh | executable | indexed executable | Discovered from the local executable index. |
pem2openpgp | executable | indexed executable | Discovered from the local executable index. |
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 generated2026-08-03
manager version0.44
manager updated2026-05-25
local dataunknown
upstreamnot available
latest detectednot detected
- okNo freshness warnings were generated.
install metadata
Package metadata
| Package key | brew:monkeysphere |
|---|---|
| Version | 0.44 |
| Package manager | Homebrew |
| Homepage | https://tracker.debian.org/pkg/monkeysphere |
| Last updated | 2026-05-25T17:02:24-04:00 |
| Pulse | updated |
| Bottle | not recorded |
| Service | none declared |
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
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
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
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.
Used sources
- Geiger risk classifier
- cross-ecosystem install command graph
- curated package history
- external package-manager database matches
- pkg.so package database
- pkgdb category and tag curation