SSH

date : 2023-07-31

SSH provides a mechanism for establishing a cryptographically secured connection between two parties, authenticating each side to the other, and passing commands and output back and forth.
te both parties.

  • exchange public/private temp keys
  • exchange symmetrical keys
  • exchange public/private keys of authentication

[Understanding Symmetric Encryption, Asymmetric Encryption, and Hashes]

Symmetric keys are used by SSH in order to encrypt the entire connection. Contrary to what some users assume, public/private asymmetrical key pairs that can be created are only used for authentication, not encrypting the connection. The symmetrical encryption allows even password authentication to be protected against snooping.

The client and server both contribute toward establishing this key, and the resulting secret is never known to outside parties. The secret key is created through a process known as a key exchange algorithm. This exchange results in the server and client both arriving at the same key independently by sharing certain pieces of public data and manipulating them with certain secret data. This process is explained in greater detail later on.

The symmetrical encryption key created by this procedure is session-based and constitutes the actual encryption for the data sent between server and client. Once this is established, the rest of the data must be encrypted with this shared secret. This is done prior to authenticating a client.

SSH can be configured to use a variety of different symmetrical cipher systems, including Advanced Encryption Standard (AES), Blowfish, 3DES, CAST128, and Arcfour. The server and client can both decide on a list of their supported ciphers, ordered by preference. The first option from the client’s list that is available on the server is used as the cipher algorithm in both directions.

On Ubuntu 20.04, both the client and the server are defaulted like the following:

  • chacha20-poly1305@openssh.com
  • aes128-ctr
  • aes192-ctr
  • aes256-ctr
  • aes128-gcm@openssh.com
  • aes256-gcm@openssh.com

[Asymmetrical Encryption]

SSH uses asymmetric encryption in a few different places.

  • During the initial key exchange process used to set up the symmetrical encryption (used to encrypt the session), asymmetrical encryption is used. In this stage, both parties produce temporary key pairs and exchange the public key in order to produce the shared secret that will be used for symmetrical encryption.
  • key-based authentication. SSH key pairs can be used to authenticate a client to a server. The client creates a key pair and then uploads the public key to any remote server it wishes to access. This is placed in a file called authorized_keys within the ~/.ssh directory in the user account’s home directory on the remote server.

After the symmetrical encryption is established to secure communications between the server and client, the client must authenticate to be allowed access. The server can use the public key in this file to encrypt a challenge message to the client. If the client can prove that it was able to decrypt this message, it has demonstrated that it owns the associated private key. Then the server can set up the environment for the client.

[Hashing]

Given these properties, hashes are mainly used for data integrity purposes and to verify the authenticity of communication. The main use in SSH is with HMAC, or hash-based message authentication codes. These are used to ensure the message text that’s received is intact and unmodified.

As part of the symmetrical encryption negotiation outlined previously, a message authentication code (MAC) algorithm is selected. The algorithm is chosen by working through the client’s list of acceptable MAC choices. The first one on this list that the server supports will be used.

Each message sent after the encryption is negotiated must contain a MAC so that the other party can verify the packet integrity. The MAC is calculated from the symmetrical shared secret, the packet sequence number of the message, and the actual message content.

The MAC itself is sent outside of the symmetrically encrypted area as the final part of the packet. Researchers generally recommend this method of encrypting the data first and then calculating the MAC.

[Understanding How SSH Works]

You probably already have a basic understanding of how SSH works. The SSH protocol employs a client-server model to authenticate two parties and encrypt the data between them.

The server component listens on a designated port for connections. It is responsible for negotiating the secure connection, authenticating the connecting party, and spawning the correct environment if the credentials are accepted.

The client is responsible for beginning the initial transmission control protocol (TCP) handshake with the server, negotiating the secure connection, verifying that the server’s identity matches previously recorded information, and providing credentials to authenticate.

An SSH session is established in two separate stages. The first is to agree upon and establish encryption to protect future communication. The second stage is to authenticate the user and discover whether access to the server should be granted.

[Negotiating Encryption for the Session]

When a TCP connection is made by a client, the server responds with the protocol versions it supports. If the client can match one of the acceptable protocol versions, the connection continues. The server also provides its public host key, which the client can use to check whether this was the intended host.

At this point, both parties negotiate a session key using a version of something called the diffie-hellman algo.

The session key will be used to encrypt the entire session. The public and private key pairs used for this part of the procedure are completely separate from the SSH keys used to authenticate a client to the server.

The shared secret encryption that is used for the rest of the connection is called binary packet protocol.

The generated secret is a symmetric key, meaning that the same key used to encrypt a message can be used to decrypt it on the other side. The purpose of this is to wrap all further communication in an encrypted tunnel that cannot be deciphered by outsiders.

After the session encryption is established, the user authentication stage begins.

Authenticating the User’s Access to the Server

The next step involves authenticating the user and deciding on access. There are a few methods that can be used for authentication, based on what the server accepts.

The general method is password authentication, which is when the server prompts the client for the password of the account they are attempting to log in with. The password is sent through the negotiated encryption, so it is secure from outside parties.

Even though the password will be encrypted, this method is not generally recommended due to the limitations on the complexity of the password. Automated scripts can break passwords of normal lengths very easily compared to other authentication methods.

The most popular and recommended alternative is the use of SSH key pairs. SSH key pairs are asymmetric keys, meaning that the two associated keys serve different functions.

The public key is used to encrypt data that can only be decrypted with the private key. The public key can be freely shared, because, although it can encrypt for the private key, there is no method of deriving the private key from the public key.

Authentication using SSH key pairs begins after the symmetric encryption has been established as described in the previous section. The procedure happens as follows:

  • The client begins by sending an ID for the key pair it would like to authenticate with to the server.
  • The server checks the authorized_keys file of the account that the client is attempting to log into for the key ID.
  • If a public key with a matching ID is found in the file, the server generates a random number and uses the public key to encrypt the number.
  • The server sends the client this encrypted message.
  • If the client actually has the associated private key, it will be able to decrypt the message using that key, revealing the original number.
  • The client combines the decrypted number with the shared session key that is being used to encrypt the communication, and calculates the MD5 hash of this value. MD5 is a message-digest algorithm that uses the hash function to generate a 128-bit hash value.
  • The client then sends this MD5 hash back to the server as an answer to the encrypted number message.
  • The server uses the same shared session key and the original number that it sent to the client to calculate the MD5 value on its own. It compares its own calculation to the one that the client sent back. If these two values match, it proves that the client was in possession of the private key and the client is authenticated.

In sum, the asymmetry of the keys allows the server to encrypt messages to the client using the public key. The client can then prove that it holds the private key by decrypting the message correctly. The two types of encryption that are used (symmetric shared secret and asymmetric public/private keys) are each able to leverage their specific strengths in this model.

Comments on page :
Let me point out an error regarding asymmetric encryption: “This is a one-way ability, meaning that the public key has no ability to decrypt the messages it writes, nor can it decrypt anything the private key may send it.”
The first part is correct: You cannot use any of those two keys to decrypt a message encrypted with the same key.
The second part is wrong: You can use either of those keys to decrypt a message encrypted with the other one.