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Learn OpenSSL with a real world cheatsheet

Experts with David Bombal, Ed Harmoush, and David Bombal

OpenSSL is the universal tool for inspecting, diagnosing, and troubleshooting SSL & TLS.

OpenSSL is composed of many different utilities, each of which is responsible for a specific aspect of the SSL and TLS ecosystem.

Topics include:

Read more

OpenSSL is the universal tool for inspecting, diagnosing, and troubleshooting SSL & TLS.

OpenSSL is composed of many different utilities, each of which is responsible for a specific aspect of the SSL and TLS ecosystem.

Topics include:

  • Module 1 - Generating Public and Private Keys

    • Generating and inspecting RSA Keys

    • Generating and inspecting DSA Keys

    • Generating and inspecting Elliptic Curve Keys

  • Adding & Removing Encryption to RSA Keys

    • Adding and removing encryption to RSA Keys

    • OpenSSL Key Utility

    • Matching Private Keys to Certificates and CSRs

  • Module 3 - Generating Certificates and CSRs

    • Creating a CSR and Certificate using an existing Private Key

    • Creating a CSR and Certificate using a new Private Key

  • Module 4 - Inspecting Certificates and CSRs

    • Extracting specific information from Certificates and CSRs

  • Module 5 - File Formats and Conversions (

    The lessons in the course follow a section from the Cheat Sheet (available to download as part of the course).

    After completing the course and downloading the OpenSSL Cheat Sheet,you will be equipped to inspect and troubleshoot any SSL / TLS scenarios you find yourself in.

Enroll now

What's inside

Learning objectives

  • How to use openssl tools
  • How to generate public and private keys
  • How to add & remove encryption to rsa keys
  • How to generate certificates and csrs
  • Understand and convert between different file formats (pem, der, pfx)

Syllabus

Welcome!
Please download the cheatsheet
Answering your questions
Udemy Tips and Tricks
Read more
The fundamentals of SSL & TLS, and the Cryptographic tools used to secure data

Based on student feedback, I'm adding some of the lessons from my Practical TLS course as optional lessons in the OpenSSL Training course.  These will provide more context around the cryptographic tools SSL/TLS used to secure data.

If you are already familiar with SSL/TLS and basic Cryptography concepts (hashing, symmetric keys, public & private keys, RSA, DH, etc...), then feel free to skip these lessons.

Otherwise, I hope these lessons provide additional value for you as you continue with the lessons from the OpenSSL Training Course.


What is SSL / TLS? What is HTTPS?
How do SSL/TLS Protect your Data?
Anti-Replay and Non-Repudiation
Key Players of SSL -- Client, Server, Certificate Authority, and Certificates
Cryptography - Hashing
Cryptography - Data-Integrity
Cryptography - Encryption
Cryptography - Public and Private Keys
Cryptography - How TLS & SSL Use Cryptography
Cryptography - PKI - Public Key Infrastructure
Cryptography - RSA Algorithm
Cryptography -DH - Diffie-Hellman Algorithm
Cryptography - DSA - Digital Signature Algorithm
Module 1: Generating Public and Private KeysGenerating & Inspecting R
Generating & Inspecting RSA Keys
Generating & Inspecting DSA Keys
Generating & Inspecting Elliptic Curve Keys
Module 1 Files
Module 2: Inspecting RSA, DSA, and EC Keys
Adding & Removing Encryption to RSA Keys
OpenSSL Pkey Utility
Matching Private Keys to Certificates and CSRs
Module 2 Files
Module 3: Generating Certificates and CSRs
Creating a CSR and Certificate using an existing Private Key
Creating a CSR and Certificate using a new Private Key
Module 3 Files
Module 4: Inspecting Certificates and CSRs
Extracting specific information from Certificates and CSRs
Module 4 Files
Module 5 - File Formats and Conversions (PEM, DER, PFX)
Check if file is PEM, DER, or PFX
Converting files between PEM and DER formats
Converting files between PEM and PFX formats
Module 5 Files
Want to learn more?
Bonus Lecture

Good to know

Know what's good
, what to watch for
, and possible dealbreakers
Equips learners with the ability to inspect and troubleshoot SSL/TLS scenarios, which is essential for maintaining secure systems and networks
Teaches how to generate certificates and CSRs, which are crucial for implementing secure communication protocols in applications and services
Includes a downloadable OpenSSL cheat sheet, which can serve as a practical reference for real-world tasks and troubleshooting
Provides optional lessons from a Practical TLS course, offering additional context around the cryptographic tools used to secure data
Covers file format conversions (PEM, DER, PFX), which is necessary for managing and deploying certificates in various environments
Focuses on OpenSSL, a universal tool for SSL/TLS inspection, diagnosis, and troubleshooting, which is a core skill for security practitioners

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Reviews summary

Practical openssl skills with cheatsheet

According to students, this course provides highly practical skills for working with OpenSSL. Learners appreciate the accompanying cheatsheet, which serves as a valuable reference. The course is praised for explaining complex topics related to SSL/TLS and cryptography in a clear and understandable manner, making it effective for learning essential OpenSSL commands needed for tasks like key generation, certificate management, and troubleshooting.
Good coverage of core OpenSSL tasks.
"The course covers all the essential OpenSSL tasks I encounter regularly, such as key management, CSRs, certificates, and file conversions."
"It provides a solid foundation in using OpenSSL for standard operations needed in network and system administration."
"Reviewers noted that the course effectively covered the key areas outlined in the syllabus."
Complex concepts explained clearly for beginners.
"Even though OpenSSL can be intimidating, the instructor explains the commands and underlying concepts like PKI and file formats very clearly."
"The lectures break down complex topics related to cryptography and SSL/TLS in a way that is easy to follow and understand."
"Learners appreciated the instructor's ability to simplify potentially confusing topics, making the course accessible."
Focuses on real-world OpenSSL commands.
"The course is very practical, showing how to use OpenSSL for actual tasks like generating keys and inspecting certificates, which is exactly what I needed."
"It provides hands-on examples of using OpenSSL commands that are directly applicable to my job working with SSL/TLS."
"Students found the lessons on generating and inspecting keys, certificates, and CSRs particularly useful for their work environments."
Cheat sheet is a valuable, practical reference.
"The cheatsheet is an excellent resource that I can keep by my side while working. It summarizes the most common commands perfectly."
"Having the downloadable cheatsheet alongside the video lessons made learning and retaining the commands much easier. Great addition!"
"Many reviewers highlighted how useful the included cheatsheet is for quickly looking up commands and syntax after finishing the course."

Activities

Be better prepared before your course. Deepen your understanding during and after it. Supplement your coursework and achieve mastery of the topics covered in Learn OpenSSL with a real world cheatsheet with these activities:
Review Cryptography Fundamentals
Solidify your understanding of the underlying cryptographic principles that OpenSSL relies on. This will make the tool's functions and options more intuitive.
Browse courses on Cryptography
Show steps
  • Review basic encryption concepts.
  • Study hashing algorithms and their applications.
  • Understand public key infrastructure (PKI).
Read 'Bulletproof SSL and TLS'
Gain a deeper understanding of SSL/TLS protocols and their underlying principles. This book provides a comprehensive overview of the subject.
View Bulletproof TLS and PKI, Second Edition:... on Amazon
Show steps
  • Obtain a copy of 'Bulletproof SSL and TLS'.
  • Read the chapters relevant to the course topics.
  • Take notes on key concepts and configurations.
Practice Key Generation and Inspection
Reinforce your understanding of key generation and inspection using OpenSSL. Repeated practice will improve your command of the tool.
Show steps
  • Generate RSA, DSA, and EC keys using OpenSSL.
  • Inspect the generated keys using OpenSSL commands.
  • Experiment with different key sizes and parameters.
Four other activities
Expand to see all activities and additional details
Show all seven activities
Read 'Network Security with OpenSSL'
Expand your knowledge of OpenSSL's applications in network security. This book provides practical examples and use cases.
View Putting Knowledge to Work on Amazon
Show steps
  • Obtain a copy of 'Network Security with OpenSSL'.
  • Focus on chapters relevant to your interests (e.g., VPNs, certificate management).
  • Experiment with the examples provided in the book.
Create a Cheat Sheet Extension
Deepen your understanding by creating a cheat sheet extension that covers advanced OpenSSL commands or specific use cases. This will require you to research and synthesize information.
Show steps
  • Identify an area of OpenSSL not covered in the course cheat sheet.
  • Research the relevant commands and options.
  • Create a concise and informative cheat sheet entry.
Set up a Secure Web Server with OpenSSL
Apply your OpenSSL knowledge to a real-world scenario by setting up a secure web server. This will test your ability to generate certificates, configure TLS, and troubleshoot issues.
Show steps
  • Install a web server (e.g., Apache, Nginx).
  • Generate a self-signed certificate using OpenSSL.
  • Configure the web server to use the certificate for HTTPS.
  • Test the secure connection using a web browser.
Contribute to OpenSSL Documentation
Improve your understanding of OpenSSL by contributing to its documentation. This will require you to research specific commands and options, and to communicate your findings clearly.
Show steps
  • Identify an area of the OpenSSL documentation that needs improvement.
  • Research the relevant commands and options.
  • Submit a pull request with your documentation changes.

Career center

Learners who complete Learn OpenSSL with a real world cheatsheet will develop knowledge and skills that may be useful to these careers:
Security Engineer
A Security Engineer works to protect computer systems and networks. This role involves identifying security vulnerabilities, implementing security measures, and responding to security incidents. This course helps the learner to understand and work with OpenSSL, which is a universal tool for inspecting, diagnosing, and troubleshooting SSL and TLS. With the knowledge of generating public and private keys, adding and removing encryption to RSA keys, and generating certificates and Certificate Signing Requests, or CSRs, the security engineer is better equipped to secure data and maintain the integrity of systems. Learning to inspect certificates and CSRs further helps the security engineer extract specific information needed for security audits and incident response.
See salaries and explore the career path for Security Engineer
Cryptography Specialist
A Cryptography Specialist focuses on developing and implementing cryptographic algorithms and systems to secure data. The cryptography specialist uses techniques for encryption, decryption, and digital signatures. This course helps to establish a foundation in OpenSSL. You'll learn to generate public and private keys, add and remove encryption to RSA keys, and generate certificates and CSRs. The course also teaches how to inspect certificates and CSRs, and convert between different file formats, which are essential skills for anyone working with cryptography. The course may provide additional context around the cryptographic tools SSL and TLS used to secure data.
See salaries and explore the career path for Cryptography Specialist
Cybersecurity Analyst
A Cybersecurity Analyst monitors computer networks and systems for security breaches and incidents. The Cybersecurity Analyst analyzes security events, investigates potential threats, and implements security measures to protect an organization’s assets. This course helps with the fundamentals of SSL and TLS, and how to use OpenSSL tools for inspecting, diagnosing, and troubleshooting related issues. With the skills obtained from generating public and private keys, managing encryption, and working with digital certificates, the Cybersecurity Analyst is better equipped to identify and respond to potential security threats.
See salaries and explore the career path for Cybersecurity Analyst
Application Security Engineer
An Application Security Engineer focuses on securing software applications throughout the development lifecycle. This includes performing security code reviews, penetration testing, and implementing security controls. This course helps to learn how to use OpenSSL tools to generate and manage SSL/TLS certificates, which are essential for securing web applications. The Application Security Engineer can inspect certificates and CSRs to identify potential security issues. This knowledge is invaluable for ensuring that applications are protected from vulnerabilities related to SSL/TLS configurations. This course may provide additional insights on the cryptographic tools SSL and TLS uses to secure data.
See salaries and explore the career path for Application Security Engineer
Security Architect
The Security Architect designs and oversees the implementation of security systems and policies across an organization. This role requires a deep understanding of security technologies and best practices. This course helps to learn how to use OpenSSL tools to manage SSL/TLS certificates, which are critical for securing network communications and web applications. You gain the skills to generate public and private keys, manage encryption, and work with digital certificates, enabling you to design and implement robust security architectures. This course may provide optional lessons about the cryptographic tools that SSL and TLS use to secure data.
See salaries and explore the career path for Security Architect
Information Security Analyst
An Information Security Analyst is responsible for protecting an organization’s data and information systems from unauthorized access, use, disclosure, disruption, modification, or destruction. This course helps to understand how to use OpenSSL tools to inspect, diagnose, and troubleshoot SSL and TLS, which are crucial for securing data in transit. You will gain insights into generating public and private keys, managing encryption, and working with digital certificates, all vital for maintaining a secure information environment. By learning how to convert files between PEM and DER format, and other related topics, the Information Security Analyst will have critical skills.
See salaries and explore the career path for Information Security Analyst
Network Security Analyst
A Network Security Analyst monitors and protects an organization’s network infrastructure from cyber threats. The work includes analyzing network traffic, identifying intrusions, and implementing security protocols. This course helps to understand how to use OpenSSL tools for inspecting and troubleshooting SSL and TLS, which are crucial for securing network communications. You gain valuable insights into generating public and private keys, managing encryption, and working with digital certificates, all vital for maintaining a secure network environment. By learning how to convert files between PEM and DER formats, and other related topics, the Network Security Analyst has skills that will enable one to excel at the job.
See salaries and explore the career path for Network Security Analyst
IT Security Consultant
An IT Security Consultant advises organizations on how to improve their security posture. This includes assessing vulnerabilities, recommending security solutions, and implementing security policies. This course helps one learn about SSL and TLS, and how to use OpenSSL tools to inspect, diagnose, and troubleshoot related issues. The IT security consultant can use the skills gained to assess the security of web servers and applications, identify potential vulnerabilities, and recommend appropriate security measures. With the practical knowledge gained from this course, the IT security consultant is better equipped to provide actionable recommendations to clients.
See salaries and explore the career path for IT Security Consultant
Digital Forensics Analyst
A Digital Forensics Analyst investigates computer systems and digital devices to uncover evidence of cybercrimes or security incidents. This course may be helpful for developing skills in using OpenSSL tools to analyze encrypted data and digital certificates. You will understand how to extract information from certificates and CSRs, and how to decrypt encrypted data using appropriate keys and algorithms. This will allow the Digital Forensics Analyst to gather valuable evidence and reconstruct events related to security incidents. These skills enable you to analyze suspicious files and network traffic, and identify potential indicators of compromise.
See salaries and explore the career path for Digital Forensics Analyst
Cloud Security Architect
A Cloud Security Architect designs and implements security solutions for cloud-based systems and applications. The work includes configuring security controls, monitoring security events, and responding to security incidents in the cloud. This course is helpful in understanding how to use OpenSSL tools to manage SSL/TLS certificates in cloud environments. You can ensure that data transmitted to and from the cloud is encrypted and protected from unauthorized access. By learning how to generate and inspect certificates, and convert between different file formats, the Cloud Security Architect can build secure and compliant cloud solutions.
See salaries and explore the career path for Cloud Security Architect
Penetration Tester
A Penetration Tester, also known as an ethical hacker, assesses the security of computer systems and networks by simulating attacks to identify vulnerabilities. This course may be useful for developing skills in using OpenSSL tools to analyze SSL/TLS configurations and identify potential weaknesses. You will also understand how to inspect certificates and CSRs, and how to exploit vulnerabilities related to weak or misconfigured SSL/TLS settings. This will allow one to conduct more effective penetration tests and provide actionable recommendations to improve security.
See salaries and explore the career path for Penetration Tester
Systems Administrator
A Systems Administrator is responsible for managing and maintaining computer systems and servers. This includes ensuring system security and troubleshooting issues. This course may be useful in improving the ability to manage SSL and TLS configurations using OpenSSL, a critical tool for system security. You'll be able to generate and inspect RSA, DSA, and Elliptic Curve keys, add and remove encryption to RSA keys, and create and inspect certificates and CSRs. These skills are invaluable for securing systems and diagnosing SSL and TLS related problems. By understanding file formats and conversions, the System Administrator will have the tools to manage certificates effectively.
See salaries and explore the career path for Systems Administrator
DevOps Engineer
A DevOps Engineer automates and streamlines software development and deployment processes. The individual ensures that security is integrated into the development pipeline. This course is helpful for understanding how to manage SSL and TLS certificates using OpenSSL, which is important for securing web applications and services. You will be able to automate certificate generation, renewal, and deployment, as well as troubleshoot SSL and TLS related issues. By adding optional lessons from a Practical TLS course, a devops engineer can understand the cryptographic tools SSL and TLS uses to secure data.
See salaries and explore the career path for DevOps Engineer
Web Developer
A Web Developer builds and maintains websites and web applications. This role often involves implementing secure communication protocols such as HTTPS. This course may provide foundational knowledge on how to use OpenSSL tools to generate certificates and private keys, which are essential for enabling HTTPS on web servers. The web developer can ensure that sensitive data transmitted between the user and the server is encrypted and protected from eavesdropping. By learning these tools, you can better secure your web applications and protect user data. Learning the fundamentals of SSL and TLS and cryptography are very useful.
See salaries and explore the career path for Web Developer
IT Auditor
An IT Auditor evaluates an organization's IT infrastructure, security measures, and compliance with regulations. This course may be useful for gaining insights into how to assess the security of SSL/TLS configurations using OpenSSL. You'll learn how to inspect certificates and CSRs, verify the validity of encryption keys, and identify potential vulnerabilities in SSL/TLS implementations. This course may give the IT auditor the tools needed to conduct thorough security audits and ensure regulatory compliance.
See salaries and explore the career path for IT Auditor

Reading list

We've selected two books that we think will supplement your learning. Use these to develop background knowledge, enrich your coursework, and gain a deeper understanding of the topics covered in Learn OpenSSL with a real world cheatsheet.
Cover image
Bulletproof TLS and PKI, Second Edition:...
Save
Provides a comprehensive guide to SSL and TLS, covering everything from the basics of cryptography to advanced deployment strategies. It is particularly useful for understanding the context in which OpenSSL is used. The book valuable resource for anyone working with SSL/TLS, and it provides a deeper understanding of the protocols and their implementation.
Bulletproof TLS and PKI, Second Edition:...
Paperback
$$$
Cover image
Putting Knowledge to Work
Save
Provides a practical guide to using OpenSSL for network security tasks. It covers topics such as certificate management, secure communication protocols, and VPNs. It useful reference for anyone who wants to use OpenSSL to secure their network infrastructure. This book is more valuable as additional reading than it is as a current reference.
Putting Knowledge to Work
Paperback
Check
Putting Knowledge to Work
Kindle Edition
Check

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Effort
3.5 total hours
Via
Udemy
Instructors
Experts with David Bombal
Ed Harmoush
David Bombal
Language
English
Good to know
Equips learners with the ability to inspect and troubleshoot SSL/TLS scenarios, which is essential for maintaining secure systems and networks
Teaches how to generate certificates and CSRs, which are crucial for implementing secure communication protocols in applications and services
Includes a downloadable OpenSSL cheat sheet, which can serve as a practical reference for real-world tasks and troubleshooting
Provides optional lessons from a Practical TLS course, offering additional context around the cryptographic tools used to secure data
Covers file format conversions (PEM, DER, PFX), which is necessary for managing and deploying certificates in various environments
Focuses on OpenSSL, a universal tool for SSL/TLS inspection, diagnosis, and troubleshooting, which is a core skill for security practitioners
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