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Learn OpenSSL with a real world cheatsheet (Udemy.com)

Learn real world commands from the OpenSSL Cheat Sheet to troubleshoot Open SSL

Created by: Experts with David Bombal

Last updated January 2023

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What you will learn

  • 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)

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Overall Score : 92 / 100

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Course Description

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 (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

In this course, you will receiving training on how to use the following OpenSSL Utilities:

  • openssl rsa

  • openssl genrsa

  • openssl dsa

  • openssl gendsa

  • openssl dsaparam

  • openssl ec

  • openssl ecparam

  • openssl pkey

  • openssl genpkey

  • openssl x509

  • openssl req

  • openssl pkcs12

Each module contains demo files you can use to practice the commands along with each lesson.

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.


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Instructor Details

Experts with David Bombal

David Bombal, together with some of the best minds in the industry is offering courses on a wide range of topics including networking, programming and software development. Our team has decades of experience teaching students from all over the world. 

Together we can do more!

David Bombal (CCIE #11023 Emeritus) passed his Cisco Certified Internetwork Expert Routing and Switching exam in January 2003 and is one of a small percentage of Cisco Engineers that pass their CCIE labs on their first attempt.

David qualified as a Cisco Certified Systems Instructor (CCSI #22787) many years ago! He has been training Cisco courses for over 15 years and has delivered instructor led courses in various countries around the world covering a wide range of Cisco topics from CCNA to CCIE.

He has also personally developed Cisco engineer utilities such as the VPN Config Generator, software, training materials, EBooks, videos and other products which are used throughout the world.

David has designed, implemented and managed networks ranging from single sites to those that span 50 countries.



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Reviews

4.6

1,552 ratings on Udemy

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By Prajjwal Mahajan on 3/10/2026

The Course provide a good knowledge knowledge in SSL/TLS the videos are simple to follow and learn, few topics that should be included in the course are certificates chains and extended attributes, Also it will be fun to learn about he configuration of openssl

By Michael Nguyen on 7/22/2025

Section 2, the optional section was amazing. I handle SSL/TLS everyday for my org, but never really understood the deeper process in my work. Helped clarified alot of things. Highly recommend

By Mark White on 6/20/2025

Very professional. I particularly liked the "OPTIONAL" material in section 2 on SSL, TLS and Cryptography...I've been afraid of the math behind the crypto bits, and that material went deeper than I've been before without making my head hurt.

By Jason Michaud on 4/3/2024

Wish there was a module on digest signing/verify. openssl does a lot of things... the cheatsheet is free to download, don't expect any coverage on commands not in that cheatsheet. Also, constantly plugging his "real" TLS course not found on Udemy.

By Олександр on 11/24/2023

This course wasn't what I expected, thank that section 2 is present, otherwise I voted to 3. The course just shows how to write commands from the cheatsheet. I hope the TLS course will be more interesting, but this course, except for chapter 2 and a few videos from chapter 3, was useless to me

By Ruben Fuchs on 10/23/2023

Very clear, well presented, well illustrated and animated short course for getting started with the whole SSL Certificates topic and how to convert the files. Just what I needed to become more secure in handling those files and a general overview for your daily work as an admin

By Saurabh Arora on 5/3/2023

One of the best teachers I came across. The way he explains the topics with simplicity is amazing. The voice modulation for explaining is impeccable. He is very knowledgeable and I would like to get more of his lessons/courses for other network topics like embedded security to hear about his thoughts on these areas. The idea of including introductory lectures on SSL/TLS basics and Cryptography is great. Thank you teacher.

By Anonymized User on 3/25/2023

Very nicely explained all the commands, really well put together course, exactly what I was looking for. The instructor is just Ed Harmoush, not David Bombal and he is really good at teaching. This course covers all the things you need, to get started on openssl tool

By Vyas Gobinath on 9/27/2022

This course was amazing. Thank you Ed for creating such a wonderful course. special mention to David Bombal who was the reason I came to know about Ed and so many other industry experts. This course demystified the process of working with SSL certificates - especially its inspection and conversion between different formats. The second section was particularly very useful, as it gave a strong introduction on the foundational concepts. The cheat sheet is comprehensive, with a list of all the commands needed to work with certificates and will be really handy for anyone who works with SSL certificates. I really appreciate Ed for his time to create this course and I enjoyed it thoroughly. I would definitely recommend this course to anyone who wants to know about SSL certificates and work with them.

By Christopher Pollaro on 9/5/2022

Good course for learning OpenSSL and most of its commands; perhaps not for TLS/SSL in general if you are looking for that. Thought the included videos were excellent that covered the theory. For me, I would have liked a little bit of history and the use cases for the different file formats and a little bit more on the config file. Other than that, a very nice and to the point course on using OpenSSL.

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