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.

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• 2019-11-23  @Ivo I meant that using a password to make a key is a last resort solution, as passwords usually have poor entropy, and using one as a key exposes the password to off-line attacks. – curiousguy Sep 29 '11 at 20:25.
• 2020-1-21  RandomKeygen is a free mobile-friendly tool that offers randomly generated keys and passwords you can use to secure any application, service or device. KEY RandomKeygen - The Secure Password & Keygen Generator.
• 2016-12-8  Using a secure password based key derivation algorithm, like PBKDF2 from PKCS#5, it will generate a second symmetric key from your password or passphrase. This second key is used to encrypt the first key. The first key could be called the master key.
• Encryption Key Generator. The all-in-one ultimate online toolbox that generates all kind of keys! Every coder needs All Keys Generator in its favorites! It is provided for free and only supported by ads and donations.
• 2020-4-13  They're easy to guess or crack. If one of your logins is compromised, a hacker then has access to all your services.
• Encryption / Decryption: Use PBKDF2 + your password and the salt from the file to regenerate k2 and k3. If it doesn't match, either your password is wrong, or someone tampered with your file. Use k2 and the IV from the file to decrypt k1. Use k1 to encrypt or decrypt files.

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…

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Encrypting

Decrypting

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

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.

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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Jasypt stands for Java Simplified Encryption.It provides basic encryption of plain-text, numbers, binaries to secure confidential data.It is completely thread safe and provides high performance in multi-processor too.

Jasypt provides simpler ways to encrypt and decrypt text and it does not require any deep knowledge of cryptography to get started with it.Simply, feed a plain text that you want to encrypt and Jasypt will do the rest of calculation and result an encrypted text for you.This kind of encryption is one-way encryption.It also provides two way encryption mechanism. While implementing two-way encryption, apart from feeding plain-text you also require to feed the secret text and this secret text can be used to decrypt the encrypted text.

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By default, Jasypt uses PBEWithMD5AndDES encryption algorithm but it provides options to select other stronger encryption options too such as PBEWithMD5AndTripleDES The free Jasypt Online Encryption and Decryption tool below provides option for one way as well two way(simple) encryption and decryption.It also provides option to compare a plain text with Jasypt encrypted password.

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Service Password Encryption

• References

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