{emayili} Sending Encrypted Email
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In a previous post I documented what I had learned while trying to understand the structure of encrypted emails. I then took an informal Twitter poll to gauge how many people are using encrypted email messages.
It’s by no means a statistically representative sample, but I’ll go out on a limb and state that not many people are actually encrypting their email. I have a few hypotheses which might explain this:
- Maybe that’s because they don’t feel it’s necessary?
- Perhaps they find it inconvenient or difficult to set up?
- Possibly they didn’t even know that it was possible?
I think that securing your personal communications is becoming progressively more important. So I’m going to be using GnuPG to encrypt and sign emails in future.
In this post I’m going to demonstrate a new feature in {emayili}, which makes it possible to easily send encrypted messages from R. This feature leans heavily on the excellent {gpg} package developed by Jeroen Ooms.
Load Emayili
First let’s load {emayili}.
library(emayili)
packageVersion("emayili")
The encryption feature is only available from version 0.7.0.
You don’t need to explicitly load {gpg} to use encryption with {emayili}, but we’ll do so just to check on the version of GPG and create some keys to play with.
library(gpg)
gpg_version()
gpg (GnuPG) 2.2.19
libgcrypt 1.8.5
Copyright (C) 2019 Free Software Foundation, Inc.
License GPLv3+: GNU GPL version 3 or later <https://gnu.org/licenses/gpl.html>
This is free software: you are free to change and redistribute it.
There is NO WARRANTY, to the extent permitted by law.
Home: /home/wookie/.gnupg
Supported algorithms:
Pubkey: RSA, ELG, DSA, ECDH, ECDSA, EDDSA
Cipher: IDEA, 3DES, CAST5, BLOWFISH, AES, AES192, AES256, TWOFISH,
CAMELLIA128, CAMELLIA192, CAMELLIA256
Hash: SHA1, RIPEMD160, SHA256, SHA384, SHA512, SHA224
Compression: Uncompressed, ZIP, ZLIB, BZIP2
Creating Keys
We’ll set the scene by creating a few keys in a temporary location so that we don’t clobber our existing keyring.
gpg_restart(home = tempdir(), silent = TRUE)
For entertainment we’ll simulate encrypted communications around the D-Day landings. We’ll need some (obviously fictitious) email addresses and keys.
FLOTILLA <- "[email protected]" BORCHERS <- "[email protected]" SCHUNK <- "[email protected]" gpg_keygen(name = "Flotilla", email = FLOTILLA) gpg_keygen(name = "U 276 Borchers", email = BORCHERS) gpg_keygen(name = "U 348 Schunk", email = SCHUNK)
Now take a look at our keyring.
gpg_list_keys() %>% select(id, fingerprint, name)
id fingerprint name
1 A54509CACB0F295E CE08B765CA067CAA57764F5EA54509CACB0F295E Flotilla
2 0897DF3055C00B2F AAA3971869729272BBD61F730897DF3055C00B2F U 276 Borchers
3 0665C3E83FBB901B EF5AA9E78B78836AD16399180665C3E83FBB901B U 348 Schunk
Publishing Keys
Publishing those keys could be done as follows (although we won’t actually publish the keys for obvious reasons!):
gpg --keyserver keyserver.ubuntu.com --send-key CE08B765CA067CAA57764F5EA54509CACB0F295E gpg --keyserver pgp.mit.edu --send-key AAA3971869729272BBD61F730897DF3055C00B2F gpg --keyserver keys.openpgp.org --send-key 0665C3E83FBB901B
The keys can be reference by id or fingerprint.
Creating a Message
What about a message body? The message below was intercepted at 04:30 UTC on 6 June 1944 and subsequently decrypted by the codebreakers at Bletchley Park.
SUBJECT <- "Attention" TEXT <- "Immediate readiness. There are indications that the invasion has begun."
Create an {emayili} message object.
msg <- envelope(
from = FLOTILLA,
to = c(BORCHERS, SCHUNK),
subject = SUBJECT,
text = TEXT
)
Date: Mon, 06 Dec 2021 15:58:54 GMT
X-Mailer: {emayili}-0.7.0
MIME-Version: 1.0
To: [email protected],
[email protected]
From: [email protected]
Subject: Attention
Content-Type: text/plain;
charset=utf-8;
format=flowed
Content-Disposition: inline
Content-Transfer-Encoding: 7bit
Content-MD5: HvL4qIrj5lMuW+E5BW4APA==
Immediate readiness. There are indications that the invasion has begun.
This is a simple, unsecured text massage.
Sign a Message
To add a digital signature to the message use the encrypt() function and set encrypt = FALSE but sign = TRUE. It’s also possible to enable a signature using the sign option to envelope().
msg %>% encrypt(encrypt = FALSE, sign = TRUE)
Date: Mon, 06 Dec 2021 15:58:54 GMT
X-Mailer: {emayili}-0.7.0
MIME-Version: 1.0
To: [email protected],
[email protected]
From: [email protected]
Subject: Attention
Content-Type: multipart/signed;
micalg="{micalg}";
protocol="application/pgp-signature";
boundary="9c3b0106"
This is an OpenPGP/MIME signed message (RFC 4880 and 3156).
--9c3b0106
Content-Type: multipart/mixed;
boundary="dab92f94"
--dab92f94
Content-Type: text/plain;
charset=utf-8;
format=flowed
Content-Disposition: inline
Content-Transfer-Encoding: 7bit
Content-MD5: HvL4qIrj5lMuW+E5BW4APA==
Immediate readiness. There are indications that the invasion has begun.
--dab92f94
Content-Type: application/pgp-keys;
name="keys.asc"
Content-Description: OpenPGP public key
Content-Disposition: attachment; filename="keys.asc"
Content-Transfer-Encoding: quoted-printable
Content-MD5: Jm6SWeTLKhlhcxTSoIKPIg==
-----BEGIN PGP PUBLIC KEY BLOCK-----
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=3DWWtP
-----END PGP PUBLIC KEY BLOCK-----
--dab92f94--
--9c3b0106
Content-Type: application/pgp-signature;
name="signature.asc"
Content-Description: OpenPGP digital signature
Content-Disposition: attachment; filename="signature.asc"
-----BEGIN PGP SIGNATURE-----
iQGzBAABCgAdFiEEn9DzpAqtEFXz/zjqrhYxZN5GG3sFAmGuMz4ACgkQrhYxZN5G
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=I6ZJ
-----END PGP SIGNATURE-----
--9c3b0106--
The resulting message now includes:
- the public key for the sender (
PGP PUBLIC KEY) and - a digital signature (
PGP SIGNATURE).
The structure of the MIME message is such that the signature covers both the message and the public key. In this way the sender is also authenticating the validity of the public key that they are sharing. For brevity you can omit the public key by setting the public_key = FALSE option to encrypt().
The commanders of U 276 and U 348 could validate the authenticity of the message by using the published public key for [email protected].
Encrypt a Message
Signing a message establishes its authenticity, but for secure communications you’d want to encrypt the contents of the message too. Again, use the encrypt() function with encrypt = TRUE (this is the default). It’s also possible to enable encryption using the encrypt option to envelope().
msg %>% encrypt(encrypt = TRUE)
Date: Mon, 06 Dec 2021 15:58:54 GMT
X-Mailer: {emayili}-0.7.0
MIME-Version: 1.0
To: [email protected],
[email protected]
From: [email protected]
Subject: Attention
Content-Type: multipart/encrypted;
protocol="application/pgp-encrypted";
boundary="0ae1ea20"
This is an OpenPGP/MIME encrypted message (RFC 4880 and 3156).
--0ae1ea20
Content-Type: application/pgp-encrypted
Content-Description: PGP/MIME version identification
Version: 1
--0ae1ea20
Content-Type: application/octet-stream;
name="encrypted.asc"
Content-Description: OpenPGP encrypted message
Content-Disposition: inline; filename="encrypted.asc"
-----BEGIN PGP MESSAGE-----
hQGMAwHtWG1MMoT4AQv9G1rKXMwxZbZ7nri4gYYh2bGbixrIVXwE0HZgL9Nbx/IO
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XLQKjkTrdVEqObGOvectIBjvTJjhjCebJwiCCOxeopjs8nBkElpSYnY/udtTxGvw
KoKbWC1Z55q8YeKWfW3I6IslInziIEJ+wUhEA+OmcvZLs8RYlR45cW68ec/G/7Pk
HpY3hkSGFcbE2pANLNcal3PFGbTNqq609EAVZg+q2O2iX+rnV8uaersA2CF7ADWF
xMZjeHg3YELJx3MGoOlgfAwnRSClcRFTOXLPGglHhtcIN1QgZe79d7mlDkp+e7OG
R34XKvyOMP06gJUDkfpL8r8BsaB5bmSQxKLd9zODeTBTADXkuQ0p4N2D+MPYLqPx
bfNfHuNZZmNufw==
=P4tl
-----END PGP MESSAGE-----
--0ae1ea20--
The resulting message is now essentially opaque. All of the useful information (the public key of the sender, the signature and the message content) are all encrypted using the public keys of the recipients. A recipient would need to have a valid private key to decrypt the contents.
Conclusion
At Fathom Data we routinely use {emayili} for sending messages from R. This forms a core component of many of our automated workflows. Being able to encrypt those messsages, ensuring that the data we’re sending is secure, is going to be very useful indeed.
I’m very interested in feedback on this new feature. Please give it a try and let me know if there are any issues. If you find this useful, please tweet about and don’t forget to tag [@datawookie](https://twitter.com/datawookie) and [@fathomdata](https://twitter.com/fathomdata).
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