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@dreikanter
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Last active November 6, 2024 13:46
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File encryption using OpenSSL

Symmetic encryption

For symmetic encryption, you can use the following:

To encrypt:

openssl aes-256-cbc -salt -a -e -in plaintext.txt -out encrypted.txt

To decrypt:

openssl aes-256-cbc -salt -a -d -in encrypted.txt -out plaintext.txt

Asymmetric encryption

For Asymmetric encryption you must first generate your private key and extract the public key.

openssl genrsa -aes256 -out private.key 2048
openssl rsa -in private.key -pubout -out public.key

To encrypt:

openssl pkeyutl -encrypt -pubin -inkey public.key -in plaintext.txt -out encrypted.txt

To decrypt:

openssl pkeyutl -decrypt -inkey private.key -in encrypted.txt -out plaintext.txt

Encrypting files

You can't directly encrypt a large file using pkeyutl. Instead, do the following:

  • Generate a key using openssl rand, e.g. openssl rand -out keyfile 32.
  • Encrypt the key file using openssl pkeyutl.
  • Encrypt the data using openssl enc, using the generated key from step 1.
  • Package the encrypted key file with the encrypted data. The recipient will need to decrypt the key with their private key, then decrypt the data with the resulting key.

Ultimate solution for safe and high secured encode anyone file in OpenSSL and command-line:

Private key generation (encrypted private key):

openssl genrsa -aes256 -out private.pem 2048
openssl rsa -in private.pem -pubout -out public.pem

With unecrypted private key:

openssl req -x509 -nodes -days 100000 -newkey rsa:2048 -keyout private_key.pem -out certificate.pem

With encrypted private key:

openssl req -x509 -days 100000 -newkey rsa:2048 -keyout private_key.pem -out certificate.pem

With existing encrypted (unecrypted) private key:

openssl req -x509 -new -days 100000 -key private_key.pem -out certificate.pem

Encrypt a file

Encrypt binary file:

openssl smime -encrypt -binary -aes-256-cbc -in plainfile.zip -out encrypted.zip.enc -outform DER yourSslCertificate.pem

Encrypt text file:

openssl smime -encrypt -aes-256-cbc -in input.txt -out output.txt -outform DER yourSslCertificate.pem

What is what:

  • smime — ssl command for S/MIME utility (smime(1)).
  • -encrypt — chosen method for file process.
  • -binary — use safe file process. Normally the input message is converted to "canonical" format as required by the S/MIME specification, this switch disable it. It is necessary for all binary files (like a images, sounds, ZIP archives).
  • -aes-256-cbc — chosen cipher AES in 256 bit for encryption (strong). If not specified 40 bit RC2 is used (very weak). (Supported ciphers).
  • -in plainfile.zip — input file name.
  • -out encrypted.zip.enc — output file name.
  • -outform DER — encode output file as binary. If is not specified, file is encoded by base64 and file size will be increased by 30%.
  • yourSslCertificate.pem — file name of your certificate's. That should be in PEM format.

That command can very effectively a strongly encrypt any file regardless of its size or format.

Decrypt a file

Decrypt binary file:

openssl smime -decrypt -binary -in encrypted.zip.enc -inform DER -out decrypted.zip -inkey private.key -passin pass:your_password

For text files:

openssl smime -decrypt -in encrypted_input.txt -inform DER -out decrypted_input.zip -inkey private.key -passin pass:your_password

What is what:

  • -inform DER — same as -outform above.
  • -inkey private.key — file name of your private key. That should be in PEM format and can be encrypted by password.
  • -passin pass:your_password — (optional) your password for private key encrypt.

Verification

Creating a signed digest of a file:

openssl dgst -sha512 -sign private_key.pem -out digest.sha512 file.txt

Verify a signed digest:

openssl dgst -sha512 -verify public_key.pem -signature digest.sha512 file.txt

Source

@dreikanter
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@antofthy Thank you for the info!

Yes, this write-up is from 2016, and now obsolete. I've been using this method to encrypt some secrets during deployment, but now there are out-of-the-box solutions, like Rails Credentials and Ansible Vault. So I've stopped doing "manual" encryption a while ago.

@drankinatty
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drankinatty commented Oct 19, 2024

Examples of Asymmetric and File encryption should be updated to use pkeyutl instead of rsautl (rsautl was deprecated in version 3.0)

@dreikanter
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@drankinatty I've done an update.

@MaxLap
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MaxLap commented Oct 24, 2024

openssl rand 32 -out keyfile doesn't work for me. Says "rand: Use -help for summary.".

Moving the 32 to the end of the command works: openssl rand -out keyfile 32

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