This is a vagrant environment to test the PowerShell/Win32-OpenSSH service, which intents to be integrated into the upstream Portable OpenSSH project as the native SSHD for Windows.

In this environment you'll also find several language examples on how to access a machine through SSH.

Usage

Build and install the Windows 2022 base image.

Launch the SSH server machine:

vagrant up sshd --no-destroy-on-error

NB this step will also create a SSH key at tmp/ida_rsa which we will later use to connect to the vagrant account.

See the allocated SSH port:

vagrant ssh-config sshd

You should see something like:

Host sshd
  HostName 127.0.0.1
  User vagrant
  Port 2222
  ...

Try accessing the ssh server at that port with the created SSH key:

ssh -i tmp/id_rsa vagrant@127.0.0.1 -p 2222 "whoami /all"

Now try the same, but from within the Windows Client machine. First launch it:

vagrant up windows --no-destroy-on-error

Then login into the Windows Desktop, and inside a PowerShell window run:

&'C:/Program Files/OpenSSH/ssh' -i c:/vagrant/tmp/id_rsa vagrant@sshd.example.com "whoami /all"

List this repository dependencies (and which have newer versions):

export GITHUB_COM_TOKEN='YOUR_GITHUB_PERSONAL_TOKEN'
./renovate.sh

sshd audit

# general
(gen) banner: SSH-2.0-OpenSSH_for_Windows_9.5
(gen) compatibility: OpenSSH 7.4+, Dropbear SSH 2018.76+
(gen) compression: enabled (zlib@openssh.com)

# key exchange algorithms
(kex) curve25519-sha256                     -- [info] available since OpenSSH 7.4, Dropbear SSH 2018.76
                                            `- [info] default key exchange since OpenSSH 6.4
(kex) curve25519-sha256@libssh.org          -- [info] available since OpenSSH 6.4, Dropbear SSH 2013.62
                                            `- [info] default key exchange since OpenSSH 6.4
(kex) ecdh-sha2-nistp256                    -- [fail] using elliptic curves that are suspected as being backdoored by the U.S. National Security Agency
                                            `- [info] available since OpenSSH 5.7, Dropbear SSH 2013.62
(kex) ecdh-sha2-nistp384                    -- [fail] using elliptic curves that are suspected as being backdoored by the U.S. National Security Agency
                                            `- [info] available since OpenSSH 5.7, Dropbear SSH 2013.62
(kex) ecdh-sha2-nistp521                    -- [fail] using elliptic curves that are suspected as being backdoored by the U.S. National Security Agency
                                            `- [info] available since OpenSSH 5.7, Dropbear SSH 2013.62
(kex) diffie-hellman-group-exchange-sha256 (3072-bit) -- [info] available since OpenSSH 4.4
                                                      `- [info] OpenSSH's GEX fallback mechanism was triggered during testing. Very old SSH clients will still be able to create connections using a 2048-bit modulus, though modern clients will use 3072. This can only be disabled by recompiling the code (see https://github.com/openssh/openssh-portable/blob/V_9_4/dh.c#L477).
(kex) diffie-hellman-group16-sha512         -- [info] available since OpenSSH 7.3, Dropbear SSH 2016.73
(kex) diffie-hellman-group18-sha512         -- [info] available since OpenSSH 7.3
(kex) diffie-hellman-group14-sha256         -- [warn] 2048-bit modulus only provides 112-bits of symmetric strength
                                            `- [info] available since OpenSSH 7.3, Dropbear SSH 2016.73
(kex) kex-strict-s-v00@openssh.com          -- [info] pseudo-algorithm that denotes the peer supports a stricter key exchange method as a counter-measure to the Terrapin attack (CVE-2023-48795)

# host-key algorithms
(key) rsa-sha2-512 (3072-bit)               -- [info] available since OpenSSH 7.2
(key) rsa-sha2-256 (3072-bit)               -- [info] available since OpenSSH 7.2
(key) ecdsa-sha2-nistp256                   -- [fail] using elliptic curves that are suspected as being backdoored by the U.S. National Security Agency
                                            `- [warn] using weak random number generator could reveal the key
                                            `- [info] available since OpenSSH 5.7, Dropbear SSH 2013.62
(key) ssh-ed25519                           -- [info] available since OpenSSH 6.5

# encryption algorithms (ciphers)
(enc) chacha20-poly1305@openssh.com         -- [info] available since OpenSSH 6.5
                                            `- [info] default cipher since OpenSSH 6.9
(enc) aes128-ctr                            -- [info] available since OpenSSH 3.7, Dropbear SSH 0.52
(enc) aes192-ctr                            -- [info] available since OpenSSH 3.7
(enc) aes256-ctr                            -- [info] available since OpenSSH 3.7, Dropbear SSH 0.52
(enc) aes128-gcm@openssh.com                -- [info] available since OpenSSH 6.2
(enc) aes256-gcm@openssh.com                -- [info] available since OpenSSH 6.2

# message authentication code algorithms
(mac) umac-64-etm@openssh.com               -- [warn] using small 64-bit tag size
                                            `- [info] available since OpenSSH 6.2
(mac) umac-128-etm@openssh.com              -- [info] available since OpenSSH 6.2
(mac) hmac-sha2-256-etm@openssh.com         -- [info] available since OpenSSH 6.2
(mac) hmac-sha2-512-etm@openssh.com         -- [info] available since OpenSSH 6.2
(mac) umac-64@openssh.com                   -- [warn] using encrypt-and-MAC mode
                                            `- [warn] using small 64-bit tag size
                                            `- [info] available since OpenSSH 4.7
(mac) umac-128@openssh.com                  -- [warn] using encrypt-and-MAC mode
                                            `- [info] available since OpenSSH 6.2
(mac) hmac-sha2-256                         -- [warn] using encrypt-and-MAC mode
                                            `- [info] available since OpenSSH 5.9, Dropbear SSH 2013.56
(mac) hmac-sha2-512                         -- [warn] using encrypt-and-MAC mode
                                            `- [info] available since OpenSSH 5.9, Dropbear SSH 2013.56

# fingerprints
(fin) ssh-ed25519: SHA256:REDACTED
(fin) ssh-rsa: SHA256:REDACTED

# additional info
(nfo) Be aware that, while this target properly supports the strict key exchange method (via the kex-strict-?-v00@openssh.com marker) needed to protect against the Terrapin vulnerability (CVE-2023-48795), all peers must also support this feature as well, otherwise the vulnerability will still be present.  The following algorithms would allow an unpatched peer to create vulnerable SSH channels with this target: chacha20-poly1305@openssh.com.  If any CBC ciphers are in this list, you may remove them while leaving the *-etm@openssh.com MACs in place; these MACs are fine while paired with non-CBC cipher types.