OpenSSL is a toolkit for the Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols. It is also a general-purpose cryptography library.
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Wireshark
Score 9.5 out of 10
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Wireshark is a free and open source network troubleshooting tool.
I would recommend OpenSSL for just about any kind of cryptographic operations that you may need. I can't think of a particular situation where it would not be appropriate to use OpenSSL for a cryptographic function of some sort or another. If you are going to provide some sort of encryption service in a product, OpenSSL is probably the best way to get it off the ground and going. With other competitors, you may get it working, but I fear long term support and interoperability will be an issue.
Wireshark is great for enterprise networks with large amounts of data traversing the network that need a way to filter and inspect specific traffic by specific parameters (i.e. destination / source IP address, host, or type). There are use-cases for smaller environments, but the amount of time needed to learn how to effectively use the tool may not be beneficial for home / small office users.
A more user-friendly interface would be nice, but then again it is not really designed for those who are not quite comfortable with this type of software.
Changes to functionality on updates - this can sometimes happen unexpectedly and can be an annoyance.
It's very simple and easy to use, although individuals not used to managing and administering networks would take some time to get familiar with it. Once they have mastered use of the application, it's easy to stay knowledgeable about it, iteration after iteration. It is well supported online through an open-source community network of professionals who are helpful in imparting knowledge and in providing assistance.
I don't believe Wireshark has "true" support as the software is open source. However, there is an active & friendly community around Wireshark that are more than happy to help answer questions. From a comprehensive Wiki and FAQ section on the site to the Ask a Question forum and bug tracker section, there's plenty of support options to make sure your questions and issues are addressed.
LibreSSL is another option to OpenSSL, however, the sheer volume of other applications using OpenSSL and the wide support for it makes OpenSSL a compelling product.
[Wireshark] is just the go-to application. It's the tool that is taught with in school and at trade conferences. We have not had a need to even look at other tools. It's free, it had a ton of functionality, and it just works without complaint.
roi is hard to measure for openssl. It's not that it doesn't provide a significant roi, but it is in the background of an application, not the foreground.