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Question: Q: install openssl

Is there a step by step process to install latest version of openssl. I am using OS 10.8.5 on a Mac Mini, current version is OpenSSL 0.9.8y 5 Feb 2013.

This is not a server version.

Posted on Jun 19, 2014 7:32 AM

Thank you Illaass.

The Top Link had helped me. After getting it to install I did not have Path correctly. I was able to get to work on MacBook Pro but need to install xcode for make command on MacMini to try and repeat the process. Don’t know if there is an easier way to get command line tools though.

Posted on Jun 19, 2014 9:34 AM

Helpful answers

The Mac topic in:

Jun 19, 2014 8:12 AM

There are I believe three different ways to get the xcode command line tools installed.

1. Download and install the full XCode package either from the App store (free) or from the Apple Developer portal (requires developer account), then in XCode tell it to download and install the command line tools
2. Download only the command line tools installer from the Apple Developer portal (requires developer account)
3. Trigger an automated install in Terminal

I am not sure why you are installing a (newer) version of OpenSSL on a Mac. If this is with regards to the recent HeartBleed security problem then no Mac has ever had a version that is vulnerable to this issue. Ironically in this case it is precisely because the version Apple includes is out-of-date that it does not have this problem.

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OpenSSL for Mac

OpenSSL 3.0.0 LATEST

OpenSSL for Mac 2021 full offline installer setup for Mac

TLS and SSL cryptographic protocols can be implemented into your projects using the OpenSSL for Mac tool. This is basically an open source library which is compatible with several operating systems for securing data that you transfer online.

Internet Data Transfer Security

SSL and TSL protocols are commonly utilized for securing online communications. They do this using authentication keys and data encryption which keep important messages confidential.

The software gives you a reliable method for generating security keys and encrypting data. That way, sensitive information can be transferred safely online. The “C” language was used to develop the main library. There is even a command line tool which can give you access to each cipher and algorithm that is available.

Multiple Encryption Algorithms Supported

There are several encryption algorithms supported by this tool. The console can be used to generate personal certificates and keys with AES, DES, SHA-1, or MD5. Cryptography algorithms which use public keys are also supported by the library, including DSA and RSA.

Documentation is not included with the download package. However, there are numerous online resources available which explain how to implement algorithms. Since it is an open source community, you can contribute your own material to it as well.

The console is where the tools are used in this package. An inexperienced user who is only familiar with graphical interfaces might have trouble in this case. Plus, a user must know a lot about cryptography standards and encryption algorithms to successfully use the library.

Overall, OpenSSL for macOS is a powerful utility for managing and creating public keys, private keys and certificates for all kinds of projects.

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colinstein / creating_keys.md

This is a brief guide to creating a public/private key pair that can be used for OpenSSL. While the «easy» version will work, I find it convenient to generate a single PEM bundle and then export the private/public key from that as needed. This document also covers how to add and remove a password from your private key and how to make sure that keychain will automatically unlock it when you sign in.

Just make it work

Generate an ssh key-pair:

If you just pound enter through the setup procedure then you will end up with a new key pair created in the default location: /Users/yourname/.ssh/ . There will be two files:

id_rsa This is your private key, you must keep it secret and never allow anybody else to gain control of it. Treat this key like a password, keep it safe and make a backup copy. You can add it to keychain using ssh-add -K

id_rsa.pub This is your public key, you can share it freely. This part of the key is used during authentication to encode a message which can only be decoded with the private key. It cannot be used to derive the private key so there is no risk in sharing it.

When a server administrator asks for a copy of your public key, send them a copy of the id_rsa.pub file. They’ll be able to add it to your user account’s list of authorized keys and that will enable you to log in without typing a password.

Doing it the hard way

This method involves creating the keys as a bundle, exporting the public key and manually setting the permssions on all of the paths. You’ll also have to configure OpenSSH to use your new bundle for authentication.

A summary of the steps follows:

I prefer to generate a certificate using OpenSSL directly, then export the private or public-key in the necessary format as needed. The benefits to this appraoch are three- fold:

1. This is a process similar to the one you’d use to generate certificates used for other tasks like S/MIME or to become part of a signed certificate for HTTPS.
2. There is a single certificate file from which you can derive the private or public key in whichever format you need. It’s much easier to manage one key than two, or even several if you require the key in different formats.
3. You gain control over the key length, encryption method, and algorithm so that you can consciously decide to use weaker keys for old/slow hardware (e.g. the Raspberry Pi media server in your closet) and strong but slower keys where appropriate.

Default software and Mac OS X

In order to generate the key I prefer to use OpenSSL directly rather than the ssh-keygen tool. While it is possible to provide flags to ssh-keygen using OpenSSL gives us access to options that are not avaiable in the standard Mac OS X version of SSH but doesn’t require us to build the SSH client from scratch.

Unfortunately the version of OpenSSL that ships with Mac OS x is rather dated and so it’s missing some of the features of the latest versions. One of those features is the genpkey command which is the new recommended way to generate keys. Assuming you have Homebrew installed (see: https://brew.sh) you can install an up-to-date version of OpenSSL with:

Many packages that you install with homebrew are likely to depend on OpenSSL anyway so this is not a terrible idea even if you don’t care about using OpenSSL directly.

If you’re interested in rebuilding openssh you should link against LibreSSL so that passwords can be installed in your keychain.

This is a relatively new option and caution should be taken because compatibility may not be perfect. LibreSSL is not intended to be a 1:1 replacement for OpenSSL.

It appears that just building OpenSSH will not have it request key information from the Mac OS X keychain, nor will it automatically start SSH-Agent so there may be some trouble-shooting steps required if you prefer to go this path. I do not build a new version of SSH.

OpenSSH requires that keys be stored in

/.ssh and that path must be restricted so that only the user can access it. It also requires that any identify files be accessible only by the user too. Permssions for

/.ssh/config can be more relaxed but it is good practice to keep those private so as not to leak inforamtion about user names or servers you connect to.

Create the directories by running:

While this will create the directory you will have to modify the default permissions. Read/write/execute for the owner and no access for any other user is required. Recall, the execute flag on a directory allows you to view its content.

You might want to create an empty ssh config file and set appropriate permissions so that you don’t have to remember how to do it later when there’s some problem and you are half-asleep, drunk, and responding to a PagerDuty alert.

You can save a few copy steps if you’re following this guide by changing into your ssh path for the remaining steps:

The first step to generating keys is to create the bundle using OpenSSL. This approach allows us to specify a few extra options when creating keys that are normally hidden by ssh-keygen :

The options: are

genpkey is the new command for generating keys, it supercedes the old genrsa method. Mac OS X’s default OpenSSL does not have this command so building your own version is required.

-algorith rsa uses the RSA algorithm for the key and is recommended for maximum compatibility. Other options include ECDSA , which is less computationally intensive on very low-end hardware (e.g. 50 MHz ARM) and DH which has characteristics similar to RSA but is rarely used.

-aes-256-cbc is the cypher used to encrypt the bundle and causes the user to be prompted for a password. There are a number of available ciphers but AES-256-cbc is among the stronger options available and widely used too.

-outform PEM there are several output formats that you can use but PEM is widely used by open source software and tends to be the best supported. The format is also nicely encoded so that you can debug with any text editor and has the advantage of bundling the public and private key into a single file which makes them easier to move around. You can always output the public or private key from a PEM bundle that contains both.

-pkey_opt … can be specified multiple times and supplies options to the generation function. This can be specified multiple times to suplly several options

• rsa_keygen_bits:4096 sets the length of the keys produced. 1024 bits is generally considered the absolute minimum for secure communication today though there is some concern that they will be broken for well-funded attackers in the near future so 2048 bits is recommended where possible. Longer keys provide greater security however there is diminishing returns as key length increases. Also, increasing the key length also increases computational costs exponentially (by the cube of the change, so 2048 is 8x more demanding than 1024-bit). You may want to use smaller keys for slower hardware or if you find yourself frequently reconnecting due to bad connections during a session for better performance.

-out yourname.pem defines the output file for your bundle. You should store a copy of this certificate in

/.ssh so that it can be used to authenticate ssh sessions. The file must not be accessible to other users on the system so set the permissions accordingly. You should also store the file and the password somewhere safe (like in your password vault or on a USB drive in a safe deposit box).

When generating the key you will be prompted for a password. Make sure to use a very strong, unique, random password for this file. You won’t have to type it in regularly so generate it with your password vault. In a pinch you can generate a random password using OpenSSL via: openssl rand -base64 48 .

When the bundle has been generated, copy it to your

/.ssh folder and change its permissions accordingly:

I prefer to make the bundle read-only for my user so I never accidentally edit it or strip the password. chmod 0600

/.ssh/yourname.pem would also work if you don’t mind it being editable by your user.

Extracting the public key

You’ll want to be able to send the public key to other people and leave it on other computers without risking your private key. The easiest way to export your public key is using the ssh-keygen method which prints it to standard out.

You can always redirect that to a file if you want to send it via email or copy it via SFTP. Generally I prefer not to keep a copy of my public keys on disk so that I am justified in always treating

/.ssh as a secret.

Remember to either edit your

/.ssh/config to specify this bundle as the default identify file by adding the line:

Alternatively you can specify it on a host-by-host basis by using ssh command-line options: ssh -i

/.ssh/yourname.pem example.com -l someuser . When you are prompted for a password, remember that you should enter the one used when creating the bundle, not the log-in password for your computer or the remote system you are connecting to.

Finally, you should consider adding the key to your Mac OX X keychain using:

This will store the password in the login Keychain which is unlocked automatically whenever you sign in. Storing your password this way means you won’t have to re-type the password you used when creating the bundle in order to use it.

/.ssh/yourname.pem foo.example.com will also add your key to Keychain.

Public Keys and Github.com

It’s a good idea to add your public key to github.com so that you can pull from private repositories and push changes to your public repositories. You can do this at:

Once you’ve uploaded your public key, other users can download it by going to

For example, my public key is located here: https://github.com/colinstein.keys

You may want to create different key-pairs for different repositories or organizations and then use

/.ssh/config and local .gitconfig files ot manage those relationships.

After generating keys in the above manner for each github account you can configure ssh by editing

/.ssh/config and adding entries like the following for each account:

When cloing a repository you would then clone from the appropriate host:

You can also edit the existing git remote by editing the .gitconfig inside the checked out repository:

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OpenSSL for Mac

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Cryptography library and toolkit that enables developers to work with the Transport Layer Security (TLS) and Secure Sockets Layer (SSL) protocols

OpenSSL provides support for the TLS and SSL protocols, and also includes various tools used in cryptography. Note that OpenSSL is officially available only as source, so you must manually compile and install the software on your Mac.

Deploy the OpenSSL toolkit via the command line

To install the OpenSSL toolkit and library on your Mac, you must open the Terminal application, go to the OpenSSL source folder, and follow the instructions from the INSTALL file included in the archive.

For short, you must run the “./config”, “make”, “make test”, and “make install” commands, and then type openssl in the Terminal. If you need to see what OpenSSL release you are using, you can use the «version” argument.

Note that you must make sure you are using the correct PATH to reach the latest OpenSSL installation. When you install OpenSSL, you get to see the output location, and you can check the path used by default with the “which openssl” shell command.

Older OpenSSL versions are delivered with the system by default, and the old link will most likely be preserved. This means that you must configure the shell to use the correct path on your own.

Worth mentioning is that you can also install the toolkit using a package management solution such as Homebrew.

Quick access to SSL and Crypto libraries

While in OpenSSL’s command line interface, you get to see all the standard, message digest, or cipher commands supported by OpenSSL, but you do not get usage instructions.

Make sure to check the online documentation to read extensive descriptions and learn about configuration options for each of the included commands.

OpenSSL’s developers also provide a Frequently Asked Questions section where you can get details about the latest version, about how you can use the commands, and so on.

To conclude, the OpenSSL software package offers you the possibility to work with the SSL and TLS protocols or to access cryptography tools, as long as you are willing to work with the command line.

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