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SSH server & client security auditing (banner, key exchange, encryption, mac, compression, compatibility, security, etc)
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Convert type comments to annotations (#40) 
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Notes:
- variable annotations are only possible for Python 3.6 and upwards

- class names as a result of a function have to be quoted
cf https://www.python.org/dev/peps/pep-0563/#enabling-the-future-behavior-in-python-3-7

This is ongoing work for #32

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README.md

ssh-audit

ssh-audit is a tool for ssh server & client configuration auditing.

Features

  • SSH1 and SSH2 protocol server support;
  • analyze SSH client configuration;
  • grab banner, recognize device or software and operating system, detect compression;
  • gather key-exchange, host-key, encryption and message authentication code algorithms;
  • output algorithm information (available since, removed/disabled, unsafe/weak/legacy, etc);
  • output algorithm recommendations (append or remove based on recognized software version);
  • output security information (related issues, assigned CVE list, etc);
  • analyze SSH version compatibility based on algorithm information;
  • historical information from OpenSSH, Dropbear SSH and libssh;
  • runs on Linux and Windows;
  • no dependencies

Usage

usage: ssh-audit.py [-1246pbcnjvlt] <host>

   -1,  --ssh1             force ssh version 1 only
   -2,  --ssh2             force ssh version 2 only
   -4,  --ipv4             enable IPv4 (order of precedence)
   -6,  --ipv6             enable IPv6 (order of precedence)
   -p,  --port=<port>      port to connect
   -b,  --batch            batch output
   -c,  --client-audit     starts a server on port 2222 to audit client
                               software config (use -p to change port;
                               use -t to change timeout)
   -n,  --no-colors        disable colors
   -j,  --json             JSON output
   -v,  --verbose          verbose output
   -l,  --level=<level>    minimum output level (info|warn|fail)
   -t,  --timeout=<secs>   timeout (in seconds) for connection and reading
                               (default: 5)
  • if both IPv4 and IPv6 are used, order of precedence can be set by using either -46 or -64.
  • batch flag -b will output sections without header and without empty lines (implies verbose flag).
  • verbose flag -v will prefix each line with section type and algorithm name.

Server Audit Example

Below is a screen shot of the server-auditing output when connecting to an unhardened OpenSSH v5.3 service: screenshot

Client Audit Example

Below is a screen shot of the client-auditing output when an unhardened OpenSSH v7.2 client connects: client_screenshot

Hardening Guides

Guides to harden server & client configuration can be found here: https://www.ssh-audit.com/hardening_guides.html

Pre-Built Packages

Pre-built packages are available for Windows (see the releases page), on PyPI, Snap, and Homebrew.

To install from PyPI:

$ pip3 install ssh-audit

To install the Snap package:

$ snap install ssh-audit

To install on Homebrew:

$ brew install ssh-audit

ChangeLog

v2.2.1-dev (???)

  • Many Python 2 code clean-ups, testing framework improvements, pylint & flake8 fixes, and mypy type comments; credit Jürgen Gmach).
  • Suppress recommendation of token host key types.
  • Added 1 new host key types: ssh-rsa1.
  • Added 1 new ciphers: blowfish, AEAD_AES_128_GCM, AEAD_AES_256_GCM.
  • Added 2 new MACs: chacha20-poly1305@openssh.com, hmac-sha3-224.

v2.2.0 (2020-03-11)

  • Marked host key type ssh-rsa as weak due to practical SHA-1 collisions.
  • Added Windows builds.
  • Added 10 new host key types: ecdsa-sha2-1.3.132.0.10, x509v3-sign-dss, x509v3-sign-rsa, x509v3-sign-rsa-sha256@ssh.com, x509v3-ssh-dss, x509v3-ssh-rsa, sk-ecdsa-sha2-nistp256-cert-v01@openssh.com, sk-ecdsa-sha2-nistp256@openssh.com, sk-ssh-ed25519-cert-v01@openssh.com, and sk-ssh-ed25519@openssh.com.
  • Added 18 new key exchanges: diffie-hellman-group14-sha256@ssh.com, diffie-hellman-group15-sha256@ssh.com, diffie-hellman-group15-sha384@ssh.com, diffie-hellman-group16-sha384@ssh.com, diffie-hellman-group16-sha512@ssh.com, diffie-hellman-group18-sha512@ssh.com, ecdh-sha2-curve25519, ecdh-sha2-nistb233, ecdh-sha2-nistb409, ecdh-sha2-nistk163, ecdh-sha2-nistk233, ecdh-sha2-nistk283, ecdh-sha2-nistk409, ecdh-sha2-nistp192, ecdh-sha2-nistp224, ecdh-sha2-nistt571, gss-gex-sha1-, and gss-group1-sha1-.
  • Added 9 new ciphers: camellia128-cbc, camellia128-ctr, camellia192-cbc, camellia192-ctr, camellia256-cbc, camellia256-ctr, aes128-gcm, aes256-gcm, and chacha20-poly1305.
  • Added 2 new MACs: aes128-gcm and aes256-gcm.

v2.1.1 (2019-11-26)

  • Added 2 new host key types: rsa-sha2-256-cert-v01@openssh.com, rsa-sha2-512-cert-v01@openssh.com.
  • Added 2 new ciphers: des, 3des.
  • Added 3 new PuTTY vulnerabilities.
  • During client testing, client IP address is now listed in output.

v2.1.0 (2019-11-14)

  • Added client software auditing functionality (see -c / --client-audit option).
  • Added JSON output option (see -j / --json option; credit Andreas Jaggi).
  • Fixed crash while scanning Solaris Sun_SSH.
  • Added 9 new key exchanges: gss-group1-sha1-toWM5Slw5Ew8Mqkay+al2g==, gss-gex-sha1-toWM5Slw5Ew8Mqkay+al2g==, gss-group14-sha1-, gss-group14-sha1-toWM5Slw5Ew8Mqkay+al2g==, gss-group14-sha256-toWM5Slw5Ew8Mqkay+al2g==, gss-group15-sha512-toWM5Slw5Ew8Mqkay+al2g==, diffie-hellman-group15-sha256, ecdh-sha2-1.3.132.0.10, curve448-sha512.
  • Added 1 new host key type: ecdsa-sha2-1.3.132.0.10.
  • Added 4 new ciphers: idea-cbc, serpent128-cbc, serpent192-cbc, serpent256-cbc.
  • Added 6 new MACs: hmac-sha2-256-96-etm@openssh.com, hmac-sha2-512-96-etm@openssh.com, hmac-ripemd, hmac-sha256-96@ssh.com, umac-32@openssh.com, umac-96@openssh.com.

v2.0.0 (2019-08-29)

  • Forked from https://github.com/arthepsy/ssh-audit (development was stalled, and developer went MIA).
  • Added RSA host key length test.
  • Added RSA certificate key length test.
  • Added Diffie-Hellman modulus size test.
  • Now outputs host key fingerprints for RSA and ED25519.
  • Added 5 new key exchanges: sntrup4591761x25519-sha512@tinyssh.org, diffie-hellman-group-exchange-sha256@ssh.com, diffie-hellman-group-exchange-sha512@ssh.com, diffie-hellman-group16-sha256, diffie-hellman-group17-sha512.
  • Added 3 new encryption algorithms: des-cbc-ssh1, blowfish-ctr, twofish-ctr.
  • Added 10 new MACs: hmac-sha2-56, hmac-sha2-224, hmac-sha2-384, hmac-sha3-256, hmac-sha3-384, hmac-sha3-512, hmac-sha256, hmac-sha256@ssh.com, hmac-sha512, hmac-512@ssh.com.
  • Added command line argument (-t / --timeout) for connection & reading timeouts.
  • Updated CVEs for libssh & Dropbear.

v1.7.0 (2016-10-26)

  • implement options to allow specify IPv4/IPv6 usage and order of precedence
  • implement option to specify remote port (old behavior kept for compatibility)
  • add colors support for Microsoft Windows via optional colorama dependency
  • fix encoding and decoding issues, add tests, do not crash on encoding errors
  • use mypy-lang for static type checking and verify all code

v1.6.0 (2016-10-14)

  • implement algorithm recommendations section (based on recognized software)
  • implement full libssh support (version history, algorithms, security, etc)
  • fix SSH-1.99 banner recognition and version comparison functionality
  • do not output empty algorithms (happens for misconfigured servers)
  • make consistent output for Python 3.x versions
  • add a lot more tests (conf, banner, software, SSH1/SSH2, output, etc)
  • use Travis CI to test for multiple Python versions (2.6-3.5, pypy, pypy3)

v1.5.0 (2016-09-20)

  • create security section for related security information
  • match and output assigned CVE list and security issues for Dropbear SSH
  • implement full SSH1 support with fingerprint information
  • automatically fallback to SSH1 on protocol mismatch
  • add new options to force SSH1 or SSH2 (both allowed by default)
  • parse banner information and convert it to specific software and OS version
  • do not use padding in batch mode
  • several fixes (Cisco sshd, rare hangs, error handling, etc)

v1.0.20160902

  • implement batch output option
  • implement minimum output level option
  • fix compatibility with Python 2.6

v1.0.20160812

  • implement SSH version compatibility feature
  • fix wrong mac algorithm warning
  • fix Dropbear SSH version typo
  • parse pre-banner header
  • better errors handling

v1.0.20160803

  • use OpenSSH 7.3 banner
  • add new key-exchange algorithms

v1.0.20160207

  • use OpenSSH 7.2 banner
  • additional warnings for OpenSSH 7.2
  • fix OpenSSH 7.0 failure messages
  • add rijndael-cbc failure message from OpenSSH 6.7

v1.0.20160105

  • multiple additional warnings
  • support for none algorithm
  • better compression handling
  • ensure reading enough data (fixes few Linux SSH)

v1.0.20151230

  • Dropbear SSH support

v1.0.20151223

  • initial version