Automated Encryption

The idea behind automated encryption is simple: enable encryption without (much) user support. The goal is to not just protect users from passive attackers (e.g., someone listening), but also protect users from man-in-the-middle attacks and forgeries. At least, as much as possible without requiring much user support. In particular, we should only require help from the user if there is a good chance that she is being attacked.

This page is intended as a discussion base for validity display and opportunistic mail encryption and how to use the trust-model tofu+pgp for automated encryption.

What are our goals and how do we archive them?

Prevent mass surveillance

It's not difficult to imagine that all clear text emails are saved by many governments and immediately analyzed. By encrypting mail by default whenever possible, we dramatically increase the cost of this type of surveillance. For instance, the government would have to interfere with key discovery (similar to how Verizon inhibited transport level security over SMTP) to prevent users from learning about their communication partners' keys.

Solution: way to find a reasonable key without user's help. (See: WKD / WKS )

Spam phishing

Phishing is a common type of fraud. A simple example is an email that is apparently from your bank prompting you to take some action that requires you to log in. The link to the log-in site is actually to a site controlled by the attacker, which steals your credentials. Another example of such an attack is a mail containing malware in an attachment.

This type of attack can be prevented by using signatures to verify the sender's address. Since we don't require users to actively authenticate their communication partners, preventing this type of attack requires recognizing that the sender is attempting an impersonation.

Solution: there are two ways to detect this type of attack.

First, phishing attacks are successful, because the mail content and headers look authentic. That is, an integral part of phishing is imitating a person or institution to trick the mark. A common technique is to an email address that is a homograph of the real email address, e.g., using a cyrillic a in place of a latin a. Google detects these types of phishing attacks by checking that email addresses conform to unicode's highly restricted designation level. We could do something similar and show a warning if an email address doesn't pass this test.

Second, if we assume that the user will regularly receive signed emails from her bank, then we can exploit the communication history to show that signed messages from previously unseen / rarely seen email addresses shouldn't be trusted. This requires vigilance on the part of the user to realize that the message didn't verify, but should have. It also requires that the user be educated. Further, if a spammer uses the same email address & key many times, the email address may eventually appear to be trustworthy using this metric.

Targeted (spear) phishing or CEO-Fraud

This attack is similar to the spam phishing described above, but the stakes are higher. An example of this type of attack is when an assistant receives an email allegedly from the CEO requesting that the assistant immediately transfer some funds to a particular account. Unlike the above attack, in this case, the victim is targeted, and the potential monetary damage much higher.

Solution: again, automated techniques or the use of history cannot mitigate this attack; the employee must be trained to recognize certain signals. A possible mitigation is to have a list of fully trusted keys, and show messages that are signed with these keys differently. Note: this doesn't mean that the employee must necessarily curate this list; this can be done by the IT department.

Man in the Middle attacks

A Man-in-the-Middle (MitM) attack is when an adversary is actively decrypting and re-encrypting email. For this to work, the MitM must 1) get Alice and Bob to use keys that he controls and 2) re-encrypt every communication to avoid detection.

To get Alice and Bob to use keys that he controls, the MitM must intervene during the initial key discovery. In this case, we can detect the MitM attack when a valid message eventually gets through. This could occur if Alice receives a message via a channel that the attacker doesn't control.

If a good message gets through and is encrypted, Alice will be unable to decrypt it and she will probably tell Bob that something went wrong. Most likely, Alice and Bob will not be sufficiently technically savvy to diagnose the actual problem. Since everything will work when they use their usual communication channel, they will ignore the issue. To actually detect a conflict in this situation, Alice's MUA could fetch all of the keys specified in the PK-ESK packets. This may allow Alice's gpg to detect a conflict: normally the sender's MUA encrypts emails to not just the recipients, but also the sender so that the sender can later review the sent message. Note: this scenario can occur due to a misconfiguration, e.g., the message is not encrypted to Alice.

If the message is only signed, then when we fetch the key used to sign the message, we will detect a conflict. In this case, we can prompt Alice to contact Bob to figure out what the right key is, which gives us a chance of defeating the man-in-the-middle.

Note: if Bob proactively sends a message to Alice, then he will (hopefully) access Alice's key via an authenticated key stored, such as WKD, in which case, the attack would have to break the store's protection (e.g., TLS) to make sure Bob gets the attacker's key. On the other hand, if the attacker sends a forged message to Bob, and Bob just downloads the specified key from the key server, then the attacker has successfully intervened. This suggests that we should always check WKD for the right key, if possible.

If the MitM attempts to intervene after Alice and Bob have already successfully communicated, e.g., by sending Bob a forged message, then we can detect the MitM due to the conflict and we can prompt the users to exchange fingerprints to figure out the right key.

Forensic detection of attacks

If an attack happened it will typically be possible to detect what happened (which messages were read, and which messages were sent) after the fact based on the state maintained by gpg. (See limitations below)

Limitations of automation

When communication partners authenticate each other over a secure channel, e.g., exchanging business cards in person, a MitM cannot hijack the channel without the communication partners knowing. An automated system doesn't normally have access to a secure channel. But, there are different levels of insecure. For instance, if the initial key discovery is done over TLS to an accountable entity (i.e., something like WKD), this makes a MitM attack significantly more expensive than just looking up a key from a key server. But given that adversaries capable of monitoring all channels are probably capable of circumventing TLS or at least compelling mail providers to compromise their WKD using tools like National Security Letters (NSLs), WKD should not be regarded as completely authoritative.

To protect against more sophisticated attackers, an automated system can be combined with something like the web of trust. To be usable, the user must be able to distinguish these different trust levels, i.e., the cases where we have reason to believe that the connection is secure, and the cases where we know the connection is secure. (In the system described below, levels 1 & 2 correspond to a connection secured using the automated approach, and levels 3 & 4 correspond to a connection that was bootstrapped over a secure channel.)

We also need to distinguish between keys that are automatically looked up and keys that the user explicitly looks up. WKD works by identifying a key that belongs to an email address. If the user explicitly enters an email address (e.g., when encrypting), then we know that the user intended that email address. On the other hand, if we fetch a key via WKS in order to validate a signed message (e.g., we use WKS to find the key for, then we should be less confident that the key is trustworthy, and that the message is authentic.


Trust Levels

Definitions of wording:

userid: The userid on a key that matches the smtp address of the sender. userid.validity is set as follows. By default, it is marginal. If the key is fully trusted via the web of trust, then it is Fully. If the key is explicitly marked as bad or unknown, then it is Never or Unknown, respectively.

tofu: Information we have about the communication history and reflects a bit the API of gpgme_tofu_info_t. As tofu info describes key + userid pairs, this is also sometimes called "binding".

key source: The source where the key was imported from, e.g. if it was automatically imported over https, or if it comes from public keyservers.

Key with enough history for basic trust:

Level 0

Defined as:

(userid.validity <= Marginal AND
 tofu.signcount == 0 AND
 tofu.enccount == 0 AND
 key.source NOT in [cert, pka, danke, wkd])


This level is assigned to keys that were never used to verify a signature, never used for an encryption, and not obtained by a source that gives some basic indication that this key is actually controlled by the allegedly owner. That is, we have no evidence that the user can actually decrypt messages encrypted with this key. Consequently, this key should not be automatically used to encrypt a messages to this recipient.


Level 1

Defined as:

((userid.validity == Marginal AND
  tofu.validity < "Key with enough history for basic trust") AND
  key.source NOT in [cert, pka, dane, wkd]):


We have verified at least one message signed using this key, or encrypted at least one message to this key, but not more than a handful, and we didn't find the key via a convincing source (e.g., WKD).

This level means that there is some evidence that the recipient actually controls this key. Thus, it is okay to automatically encrypt to this recipient using this key. (Note: if there is a MitM, then the intended recipient will still be able to read the message so this decision will not negatively impact usability.)

We don't, however, have that much evidence that the key belongs to the stated person. For instance, the key could have been imported when the user examined a phishing mail. As such, we should not indicate to the user that the contents of the messages are in anyway valid.


Level 2

Defined as:

(userid.validity == Marginal AND
 ((tofu.validity >= "Key with enough history for basic trust") OR
  key.source IN [cert, pka, dane, wkd])):

Note: validity is computed based on the number of days on which the user verified a message / encrypted a message, not the total number of verified messages / encrypted messages.


We have verified a bunch of signatures at different times from this key and/or encrypted messages to this key a bunch of times; or, the key came from a semi-trusted source.

Given the evidence that the key is actually controlled by the stated person, it makes sense to both encrypt to this key and to show that the message is signed.

Note: a common phisher is unlikely to take the time to get to this level. Thus, non-targetted phishing mails will normally not show up as trusted.


Level 3

Defined as:

userid.validity == Full AND
"no key with ownertrust ultimate signed this userid."


The user is fully trusted, but only indirectly so, i.e., WoT, or the TOFU policy was set to good.

Level 3 and level 4 are indications that the communication partner is authenticated. The distinction between levels 3 and 4 is to provide flexibility for Organizational Measures like: You should only send restricted documents to certain keys. This can be realized by having a key be an organization key be ultimately trusted and responsible for signing those keys.

This is also the level for S/MIME Mails.


Level 4

Defined as:

userid.validity == ultimate OR
(userid.validity == full AND
 "any key with ownertrust ultimate signed this userid.")


The key is either ultimately trusted or signed by an ultimately trusted key.

See level 3 for an explanation of this level.



Time delay for level 2

Using the number of days on which we saw signed messages rather than the total number of messages that we saw to determine a key's "believability" makes it more expensive for a simple attack to work. For instance, a phisher might first send a bunch of signed spam so that if the user opens them, the key will be marked as valid (level 2). But, it is much more expensive for the attacker to retain state (the key, how many messages were sent, etc.), then just firing and forgetting.

A time delay also gives others the chance to intervene if they detect an attack, e.g., if it is against a whole organization.

HTTPS Trust as shortcut to level 2

Using HTTPS for key discovery will automatically bring a key to level 2 because in that case we have a claim by some authenticated source that this key really belongs to the according mail address.

If an attacker controls your HTTPS there are very likely cheaper and less detectable attacks on your communication then intercepting pgp encryption. e.g. compromising your system.

It's also harder to break HTTPS compared to SMTPS/IMAPS because every MUA offers to ignore certificate errors (which dirmngr does not) and a compromised router could claim that your MSP only offers SMTP / IMAP without encryption.


There should only be prominent information when reading a signed mail if:

This could be displayed as a checker or a seal ribbon or something. It should be prominent and next to the signed content. There should be a distinction between Levels two, three and four but it may be slight.

Don't treat signed mails worse then an unsigned mail

A MUA should not treat any signed mail worse then an unsigned mail. If a sender is not verified it should be displayed similar to an unsigned mail because in both cases you have no information that the Sender is actually your intended Communication partner. You may want to show a tofu Conflict more prominent as user interaction is required at this point.

Especially: ignore GPGME's Red suggestion An attacker would have removed the signature instead of invalidating it. It should be treated like an unsigned mail and only additional info in details should be shown for diagnostic purposes. Similarly when Red is set because a key is expired or so. It's not more negative then a unsigned mail so only if your MUA shows unsigned mails as "Red" may you treat signed mails this way, too ;-)

Conflict handling

A TOFU conflict occurs when there are multiple keys with the same mailbox and it is not possible to automatically determine which ones are good. For instance, if two keys are cross-signed, then they are not considered to conflict; this is just a case of the user rotating her primary key.

Conflicts occur in two situations:


  1. A MitM controlled the initial key exchange. If a good message gets through, there will be a conflict. The "new" key is the correct key.
  2. An attacker attempts a MitM attack, but the user already has the right key. The "old" key is the correct key.
  3. An attacker sends a forged message. The "old" key is the correct key, or both are bad (the first key was also due to a forgery).
  4. There is a Troll trying to hurt usability so much that automated encryption is no longer used (i.e., many forgeries resulting in gratuitous conflicts)


  1. A user generated two keys e.g. on two devices and did not cross sign them and uses both.
  2. A user lost control of his old key, and did not have a revocation certificate.

Both misuse cases should be handled on the senders side because he controls or lost control of the involved keys and can take steps / inform himself what went wrong.

The second misuse case (inaccessible key) is likely more common than the first misuse case (multiple, valid keys). The first misuse case already leads to problems: communication partners need to choose which key to use.

Losing keys can also be assisted by software that provides a bad user experience or does not follow common practices.

Resolving conflicts on the senders side

When an application makes a signature, it should check that there are no other keys with the same user id. If there are and the private key material is available, then the application should prompt the user to make a cross signature

Similarly, if a signature is verified by a MUA, there are secret keys available with the same userid, and they are not cross signed, the user should be prompted to make a cross signature.

WKD Checks

A tofu aware GUI should check when signing or from time to time if a different key is uploaded to a WKD for this userid and warn in that case. This will also make a permanent man in the middle attack by a mail service provider more expensive as it would mean providing a different key to the attacked user then to others.

Automated conflict resolution by recipients

Let us assume that there are two keys, K1 and K2, with the email address, and that they are in conflict. K1 is a key with established communication history, K2 is a key without history. But we either see a message signed from with K2 or fetch K2 through the Web Key Directory of

In this case, we cannot with certainty resolve the conflict (otherwise, we would have resolved it automatically!). Consider:

- If we discover K2 because a good message or WKD access finally got through a MitM attack, then K2 is the correct key.

- If we discover K2 due to a forgery, then K1 is the correct key.

In fact, the "correct key" could also be bad! For instance, if the user never interacted with Alice and got two different forgeries, then neither key is the correct one but when both keys are bad our conflict resolution does not harm. We are in the case where an attacker controls all your communication and does not care about detection. This attack is out of scope for automated encryption.

In case K1 is provided by WKD we can accept K1 as still valid because it's still publicly available and we can assume that a conflict would have been detectable by the sender.

If we don't have a WKD we still want to use K1 for encryption but don't show it as valid anymore.

We don't want to autoresolve to K2, because we would have two good keys and something is wrong. If a user has lost control / lost his old key and is unable to revoke it we want to create problems for the sender, so that we can get notified by the sender that the new key should be used and we can mark the old key explicitly as bad.

If K2 is available in the Web Key Directory we also don't want to autoresolve to it, because it would make an attack from the Mail Service Provider too easy. Imagine the MSP wants (or is forced) to intercept some specific communication he could ensure that for a specific communication partner a MITM key (K2) is provided. When we automatically fetch that key through WKD and automatically accept K2 as valid the attacker would have reached its goals. So we stay with K1 for encryption but don't show K1 as valid anymore to make it detectable that there is a problem.

If a WKD is not available and we assume that at least one of the keys is probably good, then in all of the situations outlined above except for one (a good message gets through a MitM attack), then the old key is the correct key.

If we consider the good message from Bob getting through a MitM attack, we find that there are two situations: the good message is signed, and the good message is signed and encrypted.

If the message is signed and encrypted, then Alice will be unable to decrypt it (because the MitM didn't reencrypt it), and we won't actually see a conflict, because we never see the signature and consequently we never see a conflict. The failing-to-decrypt message, however, will likely cause Alice to talk to Bob. But, it is unlikely that they will correctly diagnose the problem, in particular, as once the MitM is back in control, everything will continue to work. Thus, they will likely conclude that there was a misconfiguration or a bug.

If the message is only signed, then Alice fetches the key used to sign the message (since she hasn't see it before) and we detect a conflict.

We conclude that the above scenario (MitM + good signed message getting through) is sufficiently rare, so we'll automatically decide for old key if there is a conflict. But if the old key is not available through WKD anymore we show the verification status as being "not trusted" (i.e., level 1) which might spur the user to try and figure out why mails from that particular user are no longer marked as verified. So the rare MitM + good signed (but not encrypted) message is getting through will still be detectable because they won't be shown as "green" / valid anymore.


    if (K1.source == WKD)
        K1.validity = Level 2 (Tofu.validity == Basic Trust)
        K1.policy = auto
        K2.validity = Level 0 (Tofu.validity == bad)
        K2.policy = bad
        encrypt_to = K1
        K1.valididy = Level 1(Tofu.validity == conflict)
        K1.policy = ask
        K2.validity = Level 1 (Tofu.validity == conflict)
        K2.policy = ask
        encrypt_to = K1

Does this model protect against our threats?

a) When a Mail gets trough once e.g. if Mallory controls Alice's router and Alice uses an Internet Cafe once. In that case Bob would not be able to decrypt the message. That communication failure could lead to more investigation. A MUA may assist that by showing to which keys a mail was encrypted in case decryption fails.

b) If Alice publishes her key in a Web key directory Bob's MUA can detect that the key used for Alice does not match the one he always used and can signal this by not showing Alice's signatures as "Good" indicating that the communication is not protected.

The Attack is more problematic if Alice and Bob don't encrypt but just sign. In case a) this would mean that the mails that get through from the real Alice would not be shown as valid. But once a mail gets through from the real Alice the messages from both Alice and Mallory will not be shown as valid anymore, indicating that the communication is not secure.

This attack will be prevented by keeping the established key in use so messages won't get encrypted to Mallory. By not showing the validity indication anymore this attack is also detectable.

Key discovery and Opportunistic Encryption (Mail only)

A MUA should offer automated key discovery and opportunistic encryption. The WKD / WKS helps with automated key discovery and should be used (by using --locate-key)

To determine if a mail can be sent automatically encrypted:

Auto Key Retrieve

Additionally to WKD lookup, if you receive a message from an Unknown Key a MUA should automatically retrieve it from a public keyserver or a Web Key directory. This Key can then be used for opportunistic encryption because you have seen a signature it is very likely that the recipient can decrypt. (auto-key-retrieve in gnupg)

Example GpgOL

Example screenshots / UX design from GpgOL

AutomatedEncryption (last edited 2016-12-21 09:31:12 by neal)