This guide will demonstrate the steps required to encrypt and decrypt files using OpenSSL on Mac OS X. The working assumption is that by demonstrating how to encrypt a file with your own public key, you'll also be able to encrypt a file you plan to send to somebody else using their private key, though you may wish to use this approach to keep archived data safe from prying eyes.

Sep 26, 2019  The other is the public key. The other file is a public key which allows you to log into the containers and VMs you provision. When you generate the keys, you will use ssh-keygen to store the keys in a safe location so you can bypass the login prompt when connecting to your instances. To generate SSH keys in macOS, follow these steps. Sep 26, 2019 The other is the public key. The other file is a public key which allows you to log into the containers and VMs you provision. When you generate the keys, you will use ssh-keygen to store the keys in a safe location so you can bypass the login prompt when connecting to your instances. To generate SSH keys in macOS, follow these steps. Nov 10, 2011 How to Generate A Public/Private SSH Key Linux By Damien – Posted on Nov 10, 2011 Nov 18, 2011 in Linux If you are using SSH frequently to connect to a remote host, one of the way to secure the connection is to use a public/private SSH key so no password is transmitted over the network and it can prevent against brute force attack. Creating a SSH Public Key on OSX¶. You generate an SSH key through Mac OS X by using the Terminal application. Once you upload a valid public SSH key, Gerrit can authenticate you based on this key.

Too Long, Didn't Read

Assuming you've already done the setup described later in this document, that id_rsa.pub.pcks8 is the public key you want to use, that id_rsa is the private key the recipient will use, and secret.txt is the data you want to transmit…

Encrypting

Decrypting

Quick steps: Create and use an SSH public-private key pair for Linux VMs in Azure.; 4 minutes to read +4; In this article. With a secure shell (SSH) key pair, you can create virtual machines (VMs) in Azure that use SSH keys for authentication, eliminating the need for passwords to sign in.

Using Passwords

OpenSSL makes it easy to encrypt/decrypt files using a passphrase. Unfortunately, pass phrases are usually 'terrible' and difficult to manage and distribute securely.

To Encrypt a File

You can add -base64 if you expect the context of the text may be subject to being 'visible' to people (e.g., you're printing the message on a pbulic forum). If you do, you'll need to add it to the decoding step as well. You can choose from several cypers but aes-256-cbc is reasonably fast, strong, and widely supported. Base64 will increase the size of the encrypted file by approximately 30%

To Decrypt a File

You will need to provide the same password used to encrypt the file. All that changes between the encrypt and decrypt phases is the input/output file and the addition of the -d flag. If you pass an incorrect password or cypher then an error will be displayed.

Encrypting Files Using your RSA keys

RSA encryption can only work with very short sections of data (e.g. an SHA1 hash of a file, or a password) and cannot be used to encrypt a large file. The solution is to generate a strong random password, use that password to encrypt the file with AES-256 in CBC mode (as above), then encrypt that password with a public RSA key. The encrypted password will only decrypt with a matching public key, and the encrypted file will require the unique password encrypted in the by the RSA key.

Replace OpenSSL

The copy of OpenSSL bundled with Mac OS X has several issues. Mac OS X 10.7 and earlier are not PCI compliant. It is best to replace it. See here for details: http://www.dctrwatson.com/2013/07/how-to-update-openssh-on-mac-os-x/

Generate Your Private/Public Key-pair

By default your private key will be stored in

• ~/.ssh/id_rsa : This is your private key and it must be kept secret
• ~/.ssh/id_rsa.pub : This is your public key, you can share it (for example) with servers as an authorized key for your account.You can change the location of where you store your keys, but this location is typical. Typically you want to ensure the private key is chmod 600, andd the public key is chmod 644.

Generate a PKCS8 Version of Your Public Key

The default format of id_rsa.pub isn't particularly friendly. If you are going to public your key (for example) on your website so that other people can verify the authorship of files attributed to you then you'll want to distribute it in another format. I find it useful to keep a copy in my .ssh folder so I don't have to re-generate it, but you can store it anywhere you like.

Generate a One-Time-Use Password to Encrypt the File

Elite dangerous frontier key generator. The passwords used to encrypt files should be reasonably long 32+ characters, random, and never used twice. To do this we'll generate a random password which we will use to encrypt the file.

Symmetric Key

This will generate 192 bytes of random data which we will use as a key. If you think a person may need to view the contents of the key (e.g., they're going to display it on a terminal or copy/paste it between computers) then you should consider base-64 encoding it, however:

1. The password will become approximately 30% longer (and there is a limit to the length of data we can RSA-encrypt using your public key
2. The password will be 'padded' with '=' characters if it's not a multiple of 4 bytes.

A Note on Long Passwords

There is a limit to the maximum length of a message that can be encrypted using RSA public key encryption. If you want to use very long keys then you'll have to split it into several short messages, encrypt them independently, and then concatinate them into a single long string. Decrypting the password will require reversing the technique: splitting the file into smaller chuncks, decrypting them independently, and then concatinating those into the original password key file.

Encrypt the File Using the Generated Key

Now that you have a good random password, you can use that to AES encrypt a file as seen in the 'with passwords' section

Decrypting the file works the same way as the 'with passwords' section, except you'll have to pass the key.

Encrypt the Key Used to Encrypt the File

We used fast symetric encryption with a very strong password to encrypt the file to avoid limitations in how we can use asymetric encryption. Finally, we'll use asymetric encryption to encrypt the password. This solves the problem of 'how do I safely transmit the password for the encrypted file' problem. You can encrypt is using the recipients public key and they can decode it using their private key. Encrypt the password using a public key:

The recipient can decode the password using a matching private key:

Package the Encrypted File and Key

There are a number of ways to do this step, but typically you'll want just a single file you can send to the recipent to make transfer less of a pain. I'd recommend just making a tarball and delivering it through normal methods (email, sftp, dropbox, whatever). Though a secure method of exchange is obviously preferable, if you have to make the data public it should still be resistent to attempts to recover the information.

The file can be extracted in the usual way:

You may want to securely delete the unecrypted keyfile as the recipient will be able to decode it using their private key and you already have the unencrypted data.

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With a secure shell (SSH) key pair, you can create virtual machines (VMs) in Azure that use SSH keys for authentication, eliminating the need for passwords to sign in. This article shows you how to quickly generate and use an SSH public-private key file pair for Linux VMs. You can complete these steps with the Azure Cloud Shell, a macOS or Linux host, the Windows Subsystem for Linux, and other tools that support OpenSSH.

Note

VMs created using SSH keys are by default configured with passwords disabled, which greatly increases the difficulty of brute-force guessing attacks.

For more background and examples, see Detailed steps to create SSH key pairs.

For additional ways to generate and use SSH keys on a Windows computer, see How to use SSH keys with Windows on Azure.

Supported SSH key formats

Azure currently supports SSH protocol 2 (SSH-2) RSA public-private key pairs with a minimum length of 2048 bits. Other key formats such as ED25519 and ECDSA are not supported.

Create an SSH key pair

Use the ssh-keygen command to generate SSH public and private key files. By default, these files are created in the ~/.ssh directory. You can specify a different location, and an optional password (passphrase) to access the private key file. If an SSH key pair with the same name exists in the given location, those files are overwritten.

The following command creates an SSH key pair using RSA encryption and a bit length of 4096:

Private Key

If you use the Azure CLI to create your VM with the az vm create command, you can optionally generate SSH public and private key files using the --generate-ssh-keys option. The key files are stored in the ~/.ssh directory unless specified otherwise with the --ssh-dest-key-path option. The --generate-ssh-keys option will not overwrite existing key files, instead returning an error. In the following command, replace VMname and RGname with your own values:

Provide an SSH public key when deploying a VM

To create a Linux VM that uses SSH keys for authentication, specify your SSH public key when creating the VM using the Azure portal, Azure CLI, Azure Resource Manager templates, or other methods:

If you're not familiar with the format of an SSH public key, you can display your public key with the following cat command, replacing ~/.ssh/id_rsa.pub with the path and filename of your own public key file if needed:

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A typical public key value looks like this example:

If you copy and paste the contents of the public key file to use in the Azure portal or a Resource Manager template, make sure you don't copy any trailing whitespace. To copy a public key in macOS, you can pipe the public key file to pbcopy. Similarly in Linux, you can pipe the public key file to programs such as xclip.

The public key that you place on your Linux VM in Azure is by default stored in ~/.ssh/id_rsa.pub, unless you specified a different location when you created the key pair. To use the Azure CLI 2.0 to create your VM with an existing public key, specify the value and optionally the location of this public key using the az vm create command with the --ssh-key-values option. In the following command, replace VMname, RGname, and keyFile with your own values:

If you want to use multiple SSH keys with your VM, you can enter them in a space-separated list, like this --ssh-key-values sshkey-desktop.pub sshkey-laptop.pub.

SSH into your VM

With the public key deployed on your Azure VM, and the private key on your local system, SSH into your VM using the IP address or DNS name of your VM. In the following command, replace azureuser and myvm.westus.cloudapp.azure.com with the administrator user name and the fully qualified domain name (or IP address):

If you specified a passphrase when you created your key pair, enter that passphrase when prompted during the login process. The VM is added to your ~/.ssh/known_hosts file, and you won't be asked to connect again until either the public key on your Azure VM changes or the server name is removed from ~/.ssh/known_hosts.

Secret Key

If the VM is using the just-in-time access policy, you need to request access before you can connect to the VM. For more information about the just-in-time policy, see Manage virtual machine access using the just in time policy.

Public Key Definition

Next steps

What Is Public Key

• For more information on working with SSH key pairs, see Detailed steps to create and manage SSH key pairs.

• If you have difficulties with SSH connections to Azure VMs, see Troubleshoot SSH connections to an Azure Linux VM.