“

Comprehensive Training on OpenSSL:

“Understanding, Configuring, Deploying, and Troubleshooting SSL/TLS
Encryption for Secure Communications".
“
Table of Contents

1. Introduction to OpenSSL
2. Cryptography basics
3. OpenSSL command-line tools
4. OpenSSL libraries and APIs
5. SSL/TLS protocols
6. SSL/TLS configuration and deployment
7. Advanced topics
 ● What is OpenSSL?
● History and evolution of
OpenSSL

1.
● OpenSSL architecture and
components
● OpenSSL license and legal
Introduction to considerations

OpenSSL
“ What is OpenSSL??

OpenSSL is a software library that provides cryptographic

functions for data encryption, decryption, and digital signature. It's
used in a wide range of applications such as web servers, email
clients, and VPNs.
“ History and evolution of OpenSSL

OpenSSL was first released in 1998 as a fork of the SSLeay

library. It has since become one of the most widely used
open-source cryptographic libraries.
“
OpenSSL architecture and components

OpenSSL consists of several libraries and command-line utilities

that provide cryptographic functions, certificate management, and
SSL/TLS support.

1. Cryptographic Libraries
2. SSL/TLS Protocol Implementation
3. Certificate Management
4. Command-Line Utilities
5. Cryptographic Engines
6. Random Number Generator
“ OpenSSL license and legal considerations

OpenSSL is released under the Apache License 2.0, which allows

for commercial and non-commercial use. However, there have
been some legal issues related to the use of OpenSSL in
commercial software.
 ● Cryptography concepts and
terminology

2.
● Symmetric encryption and
decryption
● Asymmetric encryption and

Cryptography decryption
● Hashing and digital signatures
Basics
2.1
This section covers basic
cryptographic concepts such as
plaintext, ciphertext, keys, and
algorithms. It also introduces
Cryptography important cryptographic
terminology such as symmetric
concepts and encryption, asymmetric encryption,

terminology hashing, and digital signatures.

 Cryptography concepts and terminology(contd..)

“
Encryption:
Encryption is the process of converting plain text or data into an encoded format that
cannot be understood without a key or password. It is used to protect the confidentiality
of data.

Decryption:
Decryption is the process of converting encrypted data back into plain text using a key
or password. It is used to retrieve the original data.

Symmetric Encryption:
Symmetric encryption uses the same key for both encryption and decryption. It is a fast
encryption method and is commonly used to encrypt large amounts of data.

Asymmetric Encryption:
Asymmetric encryption uses a pair of keys, a public key and a private key, for encryption
and decryption respectively. It is slower than symmetric encryption but is more secure
and is commonly used for key exchange and digital signatures.
Cryptography concepts and terminology(contd..)

“
Hashing: Hashing is the process of converting data of any length into a fixed-length
output called a hash. The hash is unique to the input data and is used to verify the
integrity of data.

Digital Signature: A digital signature is a mathematical technique used to verify the

authenticity and integrity of a digital document or message. It is created using a private
key and can only be verified using the corresponding public key.

Key Exchange: Key exchange is the process of securely exchanging cryptographic

keys between two parties over an insecure channel.

Certificate: A certificate is a digital document that contains information about the identity
of an entity, such as an individual, organization, or website, and its corresponding public
key. It is used to verify the authenticity of the entity and establish a secure
communication channel.

Certificate Authority (CA): A certificate authority is a trusted third party that issues
digital certificates and verifies the identity of the entities that request them.
2.2
Symmetric This covers how symmetric
encryption and encryption works, including the use
of a shared secret key to encrypt
decryption and decrypt data.
Symmetric Encryption and Decryption
Symmetric encryption and decryption use the same key for both encrypting and

“
decrypting data. The key is a secret value known only to the sender and the
intended recipient of the message. The encryption algorithm takes the plaintext
(unencrypted data) and the secret key as inputs and produces the ciphertext
(encrypted data).

The process of symmetric encryption and decryption can be summarized in the

following steps:

1. Key Generation: The sender generates a secret key that will be used for
both encryption and decryption.
2. Encryption: The sender uses the secret key to encrypt the plaintext data.
The encryption algorithm takes the plaintext and the secret key as inputs
and produces the ciphertext.
3. Transmission: The sender sends the encrypted data to the recipient over
an insecure channel.
4. Decryption: The recipient uses the same secret key to decrypt the
ciphertext back into the plaintext. The decryption algorithm takes the
ciphertext and the secret key as inputs and produces the plaintext.
“
Symmetric Encryption and Decryption(Contd…)

“ The security of symmetric encryption relies on keeping the secret key

secret. If an attacker gains access to the secret key, they can decrypt the
ciphertext and access the plaintext data. Therefore, it is important to use
secure key exchange methods and protect the key from unauthorized
access.

Some examples of symmetric encryption algorithms are Advanced

Encryption Standard (AES), Data Encryption Standard (DES), and Triple
DES (3DES). These algorithms are widely used in various applications
such as data encryption, secure communication, and file encryption.
Examples for Symmetric Encryption and Decryption

“
● Encrypting a file using AES-256-CBC:

openssl enc -aes-256-cbc -salt -in plaintext.txt -out encrypted.txt

This command encrypts the file "plaintext.txt" using AES-256-CBC

encryption with a randomly generated key and initialization vector (IV), and
saves the encrypted data in the file "encrypted.txt".

● Decrypting a file using AES-256-CBC:

openssl enc -aes-256-cbc -d -in encrypted.txt -out decrypted.txt

This command decrypts the file "encrypted.txt" using AES-256-CBC

decryption with the same key and IV that were used for encryption, and
saves the decrypted data in the file "decrypted.txt".
Examples for Symmetric Encryption and Decryption

“
● Encrypting a file using DES-EDE3:

openssl enc -des-ede3 -salt -a -in plaintext.txt

This command encrypts the string "plaintext.txt" using Triple DES

(DES-EDE3) encryption with a randomly generated key and saves the
encrypted data in base64 format to the standard output.

● Decrypting a file using DES-EDE3:

echo "encryptedstring" | openssl enc -des-ede3 -d -a

This command decrypts the base64-encoded string "encryptedstring" using

Triple DES (DES-EDE3) decryption with the same key that was used for
encryption, and displays the decrypted data on the standard output.
Symmetric-key encryption standards:

“ ●
●
●
●
●
●
AES (Advanced Encryption Standard)
DES (Data Encryption Standard)
3DES (Triple Data Encryption Standard)
Blowfish
Twofish
RC4 (Rivest Cipher 4)
AES(Advanced Encryption Standard)
AES is a widely-used symmetric-key encryption algorithm that can be used for both encryption
and decryption.

“
Advantages:

● Provides strong encryption with key sizes up to 256 bits.

● Fast and efficient, making it suitable for use in a wide range of applications.
● Widely supported by modern operating systems and software.

Disadvantages:

● Vulnerable to side-channel attacks if not implemented properly.

● May be susceptible to brute-force attacks if a weak key is used.

Use case:

● AES is suitable for encrypting sensitive data such as financial transactions, electronic
medical records, and government communications.

Example usage:

● Encrypt a file using AES-256 in CBC mode:

openssl enc -aes-256-cbc -salt -in plaintext.txt -out ciphertext.enc -pass
pass:mysecretpassword
● Decrypt a file using AES-256 in CBC mode:
openssl enc -aes-256-cbc -d -in ciphertext.enc -out plaintext.txt -pass
pass:mysecretpassword
DES(Data Encryption Standard)
DES is a symmetric key encryption algorithm that uses a block cipher to encrypt data.
Advantages:

“
● Widely supported by cryptographic libraries and tools.
● Fast and efficient in software implementations.
● Has been widely studied and analyzed, which has resulted in a good understanding of its strengths
and weaknesses.

Disadvantages:

● Uses a relatively small key size, which makes it vulnerable to brute force attacks.
● The block size of 64 bits is considered too small by modern standards, which can lead to security
vulnerabilities in certain use cases.

Use case:

● DES is suitable for use cases where compatibility with legacy systems is required or where the
cost of upgrading to a more secure algorithm is prohibitive.

Example usage:

● Encrypt a file using DES with a 64-bit key:

openssl enc -des -in plaintext.txt -out ciphertext.bin -K 0123456789abcdef -iv 0
● Decrypt a file using DES:
openssl enc -d -des -in ciphertext.bin -out plaintext.txt -K 0123456789abcdef -iv 0

It is important to note that DES is considered to be insecure by modern standards, and should not be used
in situations where strong security is required. Instead, it is recommended to use more secure algorithms
such as AES or ChaCha20.
3DES(Triple Data Encryption Standard)
3DES is a variant of the DES algorithm that uses multiple rounds of encryption to improve security.
Advantages:

“
● Provides a higher level of security than DES.
● Widely supported by cryptographic libraries and tools.
● Has been widely studied and analyzed, which has resulted in a good understanding of its strengths and
weaknesses.

Disadvantages:

● Can be slower and less efficient than other encryption algorithms.

● Uses a relatively small block size of 64 bits, which can lead to security vulnerabilities in certain use cases.

Use case:

● 3DES is suitable for use cases where compatibility with legacy systems is required, but a higher level of security
is also necessary.

Example usage:

● Encrypt a file using 3DES with a 192-bit key:

openssl enc -des3 -in plaintext.txt -out ciphertext.bin -K
0123456789abcdef0123456789abcdef0123456789abcdef -iv 0
● Decrypt a file using 3DES:
openssl enc -d -des3 -in ciphertext.bin -out plaintext.txt -K
0123456789abcdef0123456789abcdef0123456789abcdef -iv 0

It is important to note that while 3DES provides a higher level of security than DES, it is still considered to be less secure
than more modern encryption algorithms such as AES or ChaCha20. If possible, it is recommended to use a more
modern algorithm for new applications.
Blowfish
Blowfish is a symmetric key block cipher designed to replace the aging DES algorithm.
Advantages:

“
● Provides a higher level of security than DES.
● Has a larger key size than DES, which makes it less vulnerable to brute force attacks.
● Has a variable block size of up to 448 bits, which makes it more flexible than some other encryption algorithms.

Disadvantages:

● Has not been as widely studied and analyzed as some other encryption algorithms.
● May be slower and less efficient than other encryption algorithms in certain use cases.

Use case:

● Blowfish is suitable for use cases where a high level of security is required and compatibility with legacy systems
is not a concern.

Example usage:

● Encrypt a file using Blowfish with a 128-bit key:

openssl enc -bf -in plaintext.txt -out ciphertext.bin -K 0123456789abcdef0123456789abcdef -iv 0
● Decrypt a file using Blowfish:
openssl enc -d -bf -in ciphertext.bin -out plaintext.txt -K 0123456789abcdef0123456789abcdef -iv 0

It is important to note that while Blowfish is a strong encryption algorithm, it has been largely superseded by more
modern algorithms such as AES or ChaCha20. If possible, it is recommended to use a more modern algorithm for new
applications.
Twofish
Twofish is a symmetric key block cipher designed to be a successor to Blowfish.
Advantages:

“
● Provides a high level of security.
● Has a larger block size than Blowfish, which makes it less vulnerable to certain types of attacks.
● Has a variable key size of up to 256 bits, which makes it more flexible than some other encryption algorithms.

Disadvantages:

● May be slower and less efficient than other encryption algorithms in certain use cases.
● Has not been as widely studied and analyzed as some other encryption algorithms.

Use case:

● Twofish is suitable for use cases where a high level of security is required and compatibility with legacy systems
is not a concern.

Example usage:

● Encrypt a file using Twofish with a 256-bit key:

openssl enc -twofish -in plaintext.txt -out ciphertext.bin -K
0123456789abcdef0123456789abcdef0123456789abcdef0123456789abcdef -iv 0
● Decrypt a file using Twofish:
openssl enc -d -twofish -in ciphertext.bin -out plaintext.txt -K
0123456789abcdef0123456789abcdef0123456789abcdef0123456789abcdef -iv 0

It is important to note that while Twofish is a strong encryption algorithm, it has been largely superseded by more
modern algorithms such as AES or ChaCha20. If possible, it is recommended to use a more modern algorithm for new
applications.
RC4(Rivest Cipher 4)
RC4 is a symmetric key stream cipher that was widely used in the past, but is now considered to be insecure due to
vulnerabilities in its key scheduling algorithm.

“
Advantages:

● Has a simple and efficient design, which makes it easy to implement in software and hardware.
● Was widely used in the past and is still supported by many cryptographic libraries and tools.

Disadvantages:

● Has been found to have vulnerabilities in its key scheduling algorithm, which can lead to security weaknesses.
● Has a relatively small key size of up to 256 bits, which makes it less secure than some other encryption
algorithms.

Use case:

● RC4 is not recommended for use in new applications due to its vulnerabilities. However, it may still be used in
legacy systems where compatibility is a concern and the risks of using RC4 are understood and accepted.

Example usage:

● Encrypt a file using RC4 with a 128-bit key:

openssl enc -rc4 -in plaintext.txt -out ciphertext.bin -K 0123456789abcdef0123456789abcdef -iv 0
● Decrypt a file using RC4:
openssl enc -d -rc4 -in ciphertext.bin -out plaintext.txt -K 0123456789abcdef0123456789abcdef -iv 0

It is important to note that RC4 is considered to be insecure and should not be used in new applications. If possible, it is
recommended to use a more modern and secure algorithm such as AES or ChaCha20.
2.3
Asymmetric
encryption and This covers how asymmetric
encryption works, including the use
decryption of public and private keys to
encrypt and decrypt data.
Asymmetric Encryption and Decryption
Asymmetric encryption and decryption use two different keys, a public key

“
and a private key, to encrypt and decrypt data. The public key is freely
available and is used to encrypt data, while the private key is kept secret
and is used to decrypt the data.

The process of asymmetric encryption and decryption can be summarized

in the following steps:

1. Key Generation: The owner of the data generates a key pair

consisting of a public key and a private key. The public key can be
freely shared with anyone, while the private key must be kept secret.
2. Encryption: The sender encrypts the data using the recipient's public
key. The encryption algorithm takes the plaintext and the public key
as inputs and produces the ciphertext.
3. Transmission: The sender sends the encrypted data to the recipient
over an insecure channel.
4. Decryption: The recipient uses their private key to decrypt the
ciphertext back into the plaintext. The decryption algorithm takes the
ciphertext and the private key as inputs and produces the plaintext.
“
Asymmetric Encryption and Decryption(Contd…)

“
The security of asymmetric encryption relies on the mathematical relationship
between the public key and the private key. The public key can be shared with
anyone without compromising the security of the system because it is
computationally infeasible to derive the private key from the public key.

Some examples of asymmetric encryption algorithms are RSA, Diffie-Hellman,

and Elliptic Curve Cryptography (ECC). These algorithms are widely used in
various applications such as secure communication, digital signatures, and key
exchange.

OpenSSL provides a set of commands and APIs for working with asymmetric
encryption and decryption. The OpenSSL commands for generating key pairs,
encrypting and decrypting data using public and private keys, and managing key
pairs are available in the OpenSSL command-line tool. The OpenSSL APIs for
working with asymmetric encryption and decryption are available in the OpenSSL
library and can be used in programming languages such as C, C++, and Python.
Examples for Asymmetric Encryption and Decryption

“
● Generating an RSA key pair:
openssl genrsa -out privatekey.pem 2048
openssl rsa -in privatekey.pem -out publickey.pem -pubout

These commands generate an RSA key pair consisting of a private key in

"privatekey.pem" and a public key in "publickey.pem".
● Encrypting a file using RSA:
openssl rsautl -encrypt -in plaintext.txt -inkey publickey.pem -pubin -out encrypted.txt

This command encrypts the file "plaintext.txt" using RSA encryption with the
public key from "publickey.pem" and saves the encrypted data in
"encrypted.txt".
● Decrypting a file using RSA:
openssl rsautl -decrypt -in encrypted.txt -inkey privatekey.pem -out decrypted.txt

This command decrypts the file "encrypted.txt" using RSA decryption with
the private key from "privatekey.pem" and saves the decrypted data in
"decrypted.txt".
Examples for Asymmetric Encryption and
Decryption(contd..)

“
● Signing a file using RSA:

openssl dgst -sha256 -sign privatekey.pem -out signature.txt plaintext.txt

This command generates a digital signature of the file "plaintext.txt" using

SHA-256 hashing and RSA signing with the private key from
"privatekey.pem" and saves the signature in "signature.txt".

● Verifying a file's signature using RSA:

openssl rsautl -decrypt -in encrypted.txt -inkey privatekey.pem -out decrypted.txt

This command verifies the digital signature in "signature.txt" of the file

"plaintext.txt" using SHA-256 hashing and RSA verification with the public
key from "publickey.pem".
Asymmetric-key encryption Standards:

“ ●
●
●
●
●
RSA (Rivest-Shamir-Adleman)
Elliptic Curve Cryptography (ECC)
Diffie-Hellman key exchange
ElGamal
Digital Signature Algorithm (DSA)