Internet-Draft Stateless OpenPGP Command Line Interface March 2024
Gillmor Expires 2 September 2024 [Page]
Intended Status:
D. K. Gillmor

Stateless OpenPGP Command Line Interface


This document defines a generic stateless command-line interface for dealing with OpenPGP messages, known as sop. It aims for a minimal, well-structured API covering OpenPGP object security.

About This Document

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Table of Contents

1. Introduction

Different OpenPGP implementations have many different requirements, which typically break down in two main categories: key/certificate management and object security.

The purpose of this document is to provide a "stateless" interface that primarily handles the object security side of things, and assumes that secret key management and certificate management will be handled some other way.

Isolating object security from key/certificate management should make it easier to provide interoperability testing for the object security side of OpenPGP implementations, as described in Section 1.3.

This document defines a generic stateless command-line interface for dealing with OpenPGP messages, known here by the placeholder sop. It aims for a minimal, well-structured API.

An OpenPGP implementation should not name its executable sop to implement this specification. It just needs to provide a program that conforms to this interface.

A sop implementation should leave no trace on the system, and its behavior should not be affected by anything other than command-line arguments and input.

Obviously, the user will need to manage their secret keys (and their peers' certificates) somehow, but the goal of this interface is to separate out that task from the task of interacting with OpenPGP messages.

While this document identifies a command-line interface, the rough outlines of this interface should also be amenable to relatively straightforward library implementations in different languages.

1.1. Requirements Language

The key words "MUST", "MUST NOT", "REQUIRED", "SHALL", "SHALL NOT", "SHOULD", "SHOULD NOT", "RECOMMENDED", "NOT RECOMMENDED", "MAY", and "OPTIONAL" in this document are to be interpreted as described in BCP 14 [RFC2119] [RFC8174] when, and only when, they appear in all capitals, as shown here.

1.2. Terminology

This document uses the term "key" to refer exclusively to OpenPGP Transferable Secret Keys (see Section 11.2 of [RFC4880]).

It uses the term "certificate" to refer to OpenPGP Transferable Public Key (see Section 11.1 of [RFC4880]).

"Stateless" in "Stateless OpenPGP" means avoiding secret key and certificate state. The user is responsible for managing all OpenPGP certificates and secret keys themselves, and passing them to sop as needed. The user should also not be concerned that any state could affect the underlying operations.

OpenPGP revocations can have "Reason for Revocation" (Section of [RFC4880]), which can be either "soft" or "hard". The set of "soft" reasons is: "Key is superseded" and "Key is retired and no longer used". All other reasons (and revocations that do not state a reason) are "hard" revocations.

This document refers to a special verification-only subset of the sop command-line interface as sopv (see Section 3 for more details).

1.3. Using sop in a Test Suite

If an OpenPGP implementation provides a sop interface, it can be used to test interoperability (e.g., [OpenPGP-Interoperability-Test-Suite]).

Such an interop test suite can, for example, use custom code (not sop) to generate a new OpenPGP object that incorporates new primitives, and feed that object to a stable of sop implementations, to determine whether those implementations can consume the new form.

Or, the test suite can drive each sop implementation with a simple input, and observe which cryptographic primitives each implementation chooses to use as it produces output.

1.4. Semantics vs. Wire Format

The semantics of sop are deliberately simple and very high-level compared to the vast complexity and nuance available within the OpenPGP specification. This reflects the perspective of nearly every piece of tooling that relies on OpenPGP to accomplish its task: most toolchains don't care about the specifics, they just want the high-level object security properties.

Given this framing, this document generally tries to avoid overconstraining the details of the wire format objects emitted, or what kinds of wire format structures should be acceptable or unacceptable. This allows a test suite to evaluate and contrast the wire format choices made by different implementations in as close to their native configuration as possible. It also makes it easier to promote interoperability by ensuring that the native wire formats emitted by one implementation can be consumed by another, without relying on their choices of wire format being constrained by this draft.

Where this draft does identify specific wire format requirements, that might be due to an ambiguity in the existing specifications (which maybe needs fixing elsewhere), or to a bug in this specification that could be improved.

2. Examples

These examples show no error checking, but give a flavor of how sop might be used in practice from a shell.

The key and certificate files described in them (e.g., alice.sec) could be for example those found in [I-D.draft-bre-openpgp-samples-01].

sop generate-key "Alice Lovelace <alice@openpgp.example>" > alice.sec
sop extract-cert < alice.sec > alice.pgp

sop generate-key "Bob Babbage <bob@openpgp.example>" > bob.sec
sop extract-cert < bob.sec > bob.pgp

sop sign --as=text alice.sec < statement.txt > statement.txt.asc
sop verify statement.txt.asc alice.pgp < statement.txt

sop encrypt --sign-with=alice.sec bob.pgp < msg.eml > ciphertext.asc
sop decrypt bob.sec < ciphertext.asc > cleartext.eml

See Section 7 for more information about errors and error handling.

3. sopv Subset

While the primary goal of this document is to provide a full sop interface, as a special case, an implementer may choose to produce a version of the command-line interface that only supports OpenPGP signature verification. As a shorthand, this document refers to such an interface as sopv, or "the sopv subset". This can be useful for constrained environments where the only thing needed is signature verification, for example, system installation or update media.

A full implementation of sop by definition provides sopv, of course.

Only the following subcommands and their associated options MUST be implemented for sopv:

3.1. sopv Versioning

The abstract sopv interface is itself versioned using [SEMVER]. The definition of the relevant subcommands and options specified in this document is known as sopv version 1.0.

If backward-incompatible changes are made to the sopv subset, the major version number will be increased. If the sopv subset is extended without backward-incompatible changes, the minor version number will be increased.

Elements of the CLI relevant to sopv are annotated in this document with the sopv version in which they were introduced.

4. Subcommands

sop uses a subcommand interface, similar to those popularized by systems like git and svn.

If the user supplies a subcommand that sop does not implement, it fails with UNSUPPORTED_SUBCOMMAND. If a sop implementation does not handle a supplied option for a given subcommand, it fails with UNSUPPORTED_OPTION.

All subcommands that produce OpenPGP material on standard output produce ASCII-armored (Section 6 of [I-D.ietf-openpgp-crypto-refresh-10]) objects by default (except for sop dearmor). These subcommands have a --no-armor option, which causes them to produce binary OpenPGP material instead.

All subcommands that accept OpenPGP material on input should be able to accept either ASCII-armored or binary inputs (see Section 10.4) and behave accordingly.

See Section 6 for details about how various forms of OpenPGP material are expected to be structured.

4.1. Meta Subcommands

The subcommands grouped in this section are related to the sop implementation itself.

4.1.1. version: Version Information

sop version [--backend|--extended|--sop-spec|--sopv]
  • Standard Input: ignored

  • Standard Output: version information

This subcommand emits version information as UTF-8-encoded text.

With no arguments, the version string emitted should contain the name of the sop implementation, followed by a single space, followed by the version number. A sop implementation should use a version number that respects an established standard that is easily comparable and parsable, like [SEMVER].

If --backend is supplied, the implementation should produce a comparable line of implementation and version information about the primary underlying OpenPGP toolkit.

If --extended is supplied, the implementation may emit multiple lines of version information. The first line MUST match the information produced by a simple invocation, but the rest of the text has no defined structure.

If --sop-spec is supplied, the implementation should emit a single line of text indicating the latest version of this draft that it targets, for example, draft-dkg-openpgp-stateless-cli-06. If the implementation targets a specific draft but the implementer knows the implementation is incomplete, it should prefix the draft title with a "~" (TILDE, U+007E), for example: ~draft-dkg-openpgp-stateless-cli-06. The implementation MAY emit additional text about its relationship to the targeted draft on the lines following the versioned title.

If --sopv is supplied, the implementation should produce a single line with the implemented [SEMVER] version of the sopv interface subset (see Section 3) that this implementation provides complete coverage for. If the implementation does not provide complete coverage for any sopv interface, it should emit nothing on standard out and return UNSUPPORTED_OPTION.

--backend, --extended, --sop-spec, and --sopv are mutually-exclusive options.


$ sop version
ExampleSop 0.2.1
$ sop version --backend
LibExamplePGP 3.4.2
$ sop version --extended
ExampleSop 0.2.1
Running on MonkeyScript 4.5
LibExamplePGP 3.4.2
LibExampleCrypto 3.1.1
LibXCompression 4.0.2
See https://pgp.example/sop/ for more information
$ sop version --sop-spec

This implementation does not handle @FD: special designators for output.
$ sop version --sopv

The version subcommand and all of its options are part of the sopv subset (see Section 3) starting at sopv version 1.0.

4.1.2. list-profiles: Describe Available Profiles

sop list-profiles SUBCOMMAND

This subcommand emits a list of profiles supported by the identified subcommand. The first profile listed is the default profile, as described in Section 6.12.

If the indicated SUBCOMMAND does not accept a --profile option, it returns UNSUPPORTED_PROFILE.


$ sop list-profiles generate-key
default: use the implementer's recommendations
rfc4880: use algorithms from RFC 4880

4.2. Key and Certificate Management Subcommands

The subcommands grouped in this section are primarily intended to manipulate keys and certificates.

4.2.1. generate-key: Generate a Secret Key

sop generate-key [--no-armor]
    [--] [USERID...]

Generate a single default OpenPGP key with zero or more User IDs.

The generated secret key SHOULD be usable for as much of the sop functionality as possible. In particular:

  • It should be possible to extract an OpenPGP certificate from the key in KEYS with sop extract-cert.

  • The key in KEYS should be able to create signatures (with sop sign) that are verifiable by using sop verify with the extracted certificate.

  • Unless the --signing-only parameter is supplied, the key in KEYS should be able to decrypt messages (with sop decrypt) that are encrypted by using sop encrypt with the extracted certificate.

The detailed internal structure of the certificate is left to the discretion of the sop implementation.

If the --with-key-password option is supplied, the generated key will be password-protected (locked) with the supplied password. Note that PASSWORD is an indirect data type from which the actual password is acquired (Section 6). See also the guidance on ensuring that the password is human-readable in Section 10.8.1.

If no --with-key-password option is supplied, the generated key will be unencrypted.

If the --profile argument is supplied and the indicated PROFILE is not supported by the implementation, sop will fail with UNSUPPORTED_PROFILE.

The presence of the --signing-only option is intended to create a key that is only capable of signing, not decrypting. This is useful for deployments where only signing and verification are necessary.

If any of the USERID options are not valid UTF-8, sop generate-key fails with EXPECTED_TEXT.

If the implementation rejects any USERID option that is valid UTF-8 (e.g., due to internal policy, see Section 5.2), sop generate-key fails with BAD_DATA.


$ sop generate-key 'Alice Lovelace <alice@openpgp.example>' > alice.sec
$ head -n1 < alice.sec

4.2.2. change-key-password: Update a Key's Password

sop change-key-password [--no-armor]

The output will be the same set of OpenPGP Transferable Secret Keys as the input, but with all secret key material locked according to the password indicated by the --new-key-password option (or, with no password at all, if --new-key-password is absent). Note that --old-key-password can be supplied multiple times, and each supplied password will be tried as a means to unlock any locked key material encountered. It will normalize a Transferable Secret Key to use a single password even if it originally had distinct passwords locking each of the subkeys.

If any secret key packet is locked but cannot be unlocked with any of the supplied --old-key-password arguments, this subcommand should fail with KEY_IS_PROTECTED.


# adding a password to an unlocked key:
$ sop change-key-password --new-key-password=@ENV:keypass < unlocked.key > locked.key
# removing a password:
$ sop change-key-password --old-key-password=@ENV:keypass < locked.key > unlocked.key
# changing a password:
$ sop change-key-password --old-key-password=@ENV:keypass --new-key-password=@ENV:newpass < locked.key > refreshed.key

4.2.3. revoke-key: Create a Revocation Certificate

sop revoke-key [--no-armor]

Generate a revocation certificate for each Transferable Secret Key found. See Section 10 of [I-D.ietf-openpgp-crypto-refresh-10] for a discussion of common forms of revocation certificate.


$ sop revoke-key < alice.key > alice-revoked.pgp

4.2.4. extract-cert: Extract a Certificate from a Secret Key

sop extract-cert [--no-armor]

The output should contain one OpenPGP certificate in CERTS per OpenPGP Transferable Secret Key found in KEYS. There is no guarantee what order the CERTS will be in.

sop extract-cert SHOULD work even if any of the keys in KEYS is password-protected.


$ sop extract-cert < alice.sec > alice.pgp
$ head -n1 < alice.pgp

4.3. Messaging Subcommands

The subcommands in this section handle OpenPGP messages: encrypting, decrypting, signing, and verifying.

4.3.1. sign: Create Detached Signatures

sop sign [--no-armor] [--micalg-out=MICALG]
     [--as={binary|text}] [--] KEYS [KEYS...]

Exactly one signature will be made by each key in the supplied KEYS arguments.

--as defaults to binary. If --as=text and the input DATA is not valid UTF-8 (Section 10.7), sop sign fails with EXPECTED_TEXT.

--as=binary SHOULD result in OpenPGP signatures of type 0x00 ("Signature of a binary document"). --as=text SHOULD result in OpenPGP signatures of type 0x01 ("Signature of a canonical text document"). See Section 5.2.1 of [RFC4880] for more details.

When generating PGP/MIME messages ([RFC3156]), it is useful to know what digest algorithm was used for the generated signature. When --micalg-out is supplied, sop sign emits the digest algorithm used to the specified MICALG file in a way that can be used to populate the micalg parameter for the Content-Type (see Section 6.8). If the specified MICALG file already exists in the filesystem, sop sign will fail with OUTPUT_EXISTS. When --micalg-out is supplied, the DATA on standard input should already be in canonical text form (7-bit clean, CRLF line endings, no trailing whitespace), as specified in Section 3 of [RFC3156]. If the incoming DATA does not already meet these requirements, sop sign will fail with EXPECTED_TEXT, regardless of any argument supplied for --as.

When signing with multiple keys, sop sign SHOULD use the same digest algorithm for every signature generated in a single run, unless there is some internal constraint on the KEYS objects. If --micalg-out is requested, and multiple incompatibly-constrained KEYS objects are supplied, sop sign MUST emit the empty string to the designated MICALG.

If the signing key material in any key in the KEYS objects is password-protected, sop sign SHOULD try all supplied --with-key-password options to unlock the key material until it finds one that enables the use of the key for signing. If none of the PASSWORD options unlock the key (or if no such option is supplied), sop sign will fail with KEY_IS_PROTECTED. Note that PASSWORD is an indirect data type from which the actual password is acquired (Section 6). Note also the guidance for retrying variants of a non-human-readable password in Section 10.8.2.

If any key in the KEYS objects is not capable of producing a signature, sop sign will fail with KEY_CANNOT_SIGN.

sop sign MUST NOT produce any extra signatures beyond those from KEYS objects supplied on the command line.


$ sop sign --as=text alice.sec < message.txt > message.txt.asc
$ head -n1 < message.txt.asc

4.3.2. verify: Verify Detached Signatures

sop verify [--not-before=DATE] [--not-after=DATE]

--not-before and --not-after indicate that signatures with dates outside certain range MUST NOT be considered valid.

--not-before defaults to the beginning of time. Accepts the special value - to indicate the beginning of time (i.e., no lower boundary).

--not-after defaults to the current system time (now). Accepts the special value - to indicate the end of time (i.e., no upper boundary).

sop verify only returns OK if at least one certificate included in any CERTS object made a valid signature in the time window specified over the DATA supplied.

For details about the valid signatures, the user MUST inspect the VERIFICATIONS output.

If no CERTS are supplied, sop verify fails with MISSING_ARG.

If no valid signatures are found, sop verify fails with NO_SIGNATURE.

See Section 12.1 for more details about signature verification.


(In this example, we see signature verification succeed first, and then fail on a modified version of the message.)

$ sop verify message.txt.asc alice.pgp < message.txt
2019-10-29T18:36:45Z EB85BB5FA33A75E15E944E63F231550C4F47E38E EB85BB5FA33A75E15E944E63F231550C4F47E38E mode:text signed by alice.pgp
$ echo $?
$ tr a-z A-Z < message.txt | sop verify message.txt.asc alice.pgp
$ echo $?

The verify subcommand and all of its options are part of the sopv subset (see Section 3) starting at sopv version 1.0.

4.3.3. encrypt: Encrypt a Message

sop encrypt [--as={binary|text}]
    [--] [CERTS...]

--as defaults to binary. The setting of --as corresponds to the one octet format field found in the Literal Data packet at the core of the output CIPHERTEXT. If --as is set to binary, the octet is b (0x62). If it is text, the format octet is u (0x75).

--with-password enables symmetric encryption (and can be used multiple times if multiple passwords are desired).

--sign-with creates exactly one signature by for each secret key found in the supplied KEYS object (this can also be used multiple times if signatures from keys found in separaate files are desired). If any key in any supplied KEYS object is not capable of producing a signature, sop sign will fail with KEY_CANNOT_SIGN. If any signing key material in any supplied KEYS object is password-protected, sop encrypt SHOULD try all supplied --with-key-password options to unlock the key material until it finds one that enables the use of the key for signing. If none of the --with-key-password=PASSWORD options can unlock any locked signing key material (or if no such option is supplied), sop encrypt will fail with KEY_IS_PROTECTED. All signatures made must be placed inside the encryption produced by sop encrypt.

Note that both --with-password and --with-key-password supply PASSWORD arguments, but they do so in different contexts which are not interchangeable. A PASSWORD supplied for symmetric encryption (--with-password) MUST NOT be used to try to unlock a signing key (--with-key-password) and a PASSWORD supplied to unlock a signing key MUST NOT be used to symmetrically encrypt the message. Regardless of context, each PASSWORD argument is presented as an indirect data type from which the actual password is acquired (Section 6). If sop encrypt encounters a password which is not a valid UTF-8 string (Section 10.7), or is otherwise not robust in its representation to humans, it fails with PASSWORD_NOT_HUMAN_READABLE. If sop encrypt sees trailing whitespace at the end of a password, it will trim the trailing whitespace before using the password. See Section 10.8 for more discussion about passwords.

If --as is set to binary, then --sign-with will sign as a binary document (OpenPGP signature type 0x00).

If --as is set to text, then --sign-with will sign as a canonical text document (OpenPGP signature type 0x01). In this case, if the input DATA is not valid UTF-8 (Section 10.7), sop encrypt fails with EXPECTED_TEXT.

If --sign-with is supplied for input DATA that is not valid UTF-8, sop encrypt MAY sign as a binary document (OpenPGP signature type 0x00).

sop encrypt MUST NOT produce any extra signatures beyond those from KEYS objects identified by --sign-with.

The resulting CIPHERTEXT should be decryptable by the secret keys corresponding to every certificate included in all CERTS, as well as each password given with --with-password.

If no CERTS or --with-password options are present, sop encrypt fails with MISSING_ARG.

If at least one of the identified certificates requires encryption to an unsupported asymmetric algorithm, sop encrypt fails with UNSUPPORTED_ASYMMETRIC_ALGO.

If at least one of the identified certificates is not encryption-capable (e.g., revoked, expired, no encryption-capable flags on primary key and valid subkeys), sop encrypt fails with CERT_CANNOT_ENCRYPT.

If the --profile argument is supplied and the indicated PROFILE is not supported by the implementation, sop will fail with UNSUPPORTED_PROFILE. The use of a profile for this subcommand allows an implementation faced with parametric or algorithmic choices to make a decision coarsely guided by the operator. For example, when encrypting with a password, there is no knowledge about the capabilities of the recipient, and an implementation may prefer cryptographically modern algorithms, or it may prefer more broad compatibility. In the event that a known recipient (i.e., one of the CERTS) explicitly indicates a lack of support for one of the features preferred by the indicated profile, the implementation SHOULD conform to the recipient's advertised capabilities where possible.

If --session-key-out argument is supplied, the session key generated for this encrypted will be written to the indicated location. This can be useful, for example, when Alice encrypts a message to Bob, but also wants to retain the ability to read it without having any of her own secret key material available (see Section 9.1 of [I-D.ietf-lamps-e2e-mail-guidance-11]).

If sop encrypt fails for any reason, it emits no CIPHERTEXT.


(In this example, bob.bin is a file containing Bob's binary-formatted OpenPGP certificate. Alice is encrypting a message to both herself and Bob.)

$ sop encrypt --as=text --sign-with=alice.key alice.asc bob.bin < message.eml > encrypted.asc
$ head -n1 encrypted.asc

4.3.4. decrypt: Decrypt a Message

sop decrypt [--session-key-out=SESSIONKEY]
     [--verify-not-after=DATE] ]
    [--] [KEYS...]

The caller can ask sop for the session key discovered during decryption by supplying the --session-key-out option. If the specified file already exists in the filesystem, sop decrypt will fail with OUTPUT_EXISTS. When decryption is successful, sop decrypt writes the discovered session key to the specified file.

--with-session-key enables decryption of the CIPHERTEXT using the session key directly against the SEIPD packet. This option can be used multiple times if several possible session keys should be tried. SESSIONKEY is an indirect data type from which the actual sessionkey value is acquired (Section 6).

--with-password enables decryption based on any SKESK (Section 5.3 of [I-D.ietf-openpgp-crypto-refresh-10]) packets in the CIPHERTEXT. This option can be used multiple times if the user wants to try more than one password.

--with-key-password lets the user use password-protected (locked) secret key material. If the decryption-capable secret key material in any key in the KEYS objects is password-protected, sop decrypt SHOULD try all supplied --with-key-password options to unlock the key material until it finds one that enables the use of the key for decryption. If none of the --with-key-password options unlock the key (or if no such option is supplied), and the message cannot be decrypted with any other KEYS, --with-session-key, or --with-password options, sop decrypt will fail with KEY_IS_PROTECTED.

Note that the two kinds of PASSWORD options are for different domains: --with-password is for unlocking an SKESK, and --with-key-password is for unlocking secret key material in KEYS. sop decrypt SHOULD NOT apply the --with-key-password argument to any SKESK, or the --with-password argument to any KEYS.

Each PASSWORD argument is an indirect data type from which the actual password is acquired (Section 6). If sop decrypt tries and fails to use a password supplied by a PASSWORD, and it observes that there is trailing UTF-8 whitespace at the end of the password, it will retry with the trailing whitespace stripped. See Section 10.8.2 for more discussion about consuming password-protected key material.

--verifications-out produces signature verification status to the designated file. If the designated file already exists in the filesystem, sop decrypt will fail with OUTPUT_EXISTS.

The return code of sop decrypt is not affected by the results of signature verification. The caller MUST check the returned VERIFICATIONS to confirm signature status. An empty VERIFICATIONS output indicates that no valid signatures were found.

--verify-with identifies a set of certificates whose signatures would be acceptable for signatures over this message.

If the caller is interested in signature verification, both --verifications-out and at least one --verify-with must be supplied. If only one of these options is supplied, sop decrypt fails with INCOMPLETE_VERIFICATION.

--verify-not-before and --verify-not-after provide a date range for acceptable signatures, by analogy with the options for sop verify (see Section 4.3.2). They should only be supplied when doing signature verification.

See Section 12.1 for more details about signature verification.

If no KEYS or --with-password or --with-session-key options are present, sop decrypt fails with MISSING_ARG.

If unable to decrypt, sop decrypt fails with CANNOT_DECRYPT.

sop decrypt only emits cleartext to Standard Output that was successfully decrypted.


(In this example, Alice stashes and re-uses the session key of an encrypted message.)

$ sop decrypt --session-key-out=session.key alice.sec < ciphertext.asc > cleartext.out
$ ls -l ciphertext.asc cleartext.out
-rw-r--r-- 1 user user   321 Oct 28 01:34 ciphertext.asc
-rw-r--r-- 1 user user   285 Oct 28 01:34 cleartext.out
$ sop decrypt --with-session-key=session.key < ciphertext.asc > cleartext2.out
$ diff cleartext.out cleartext2.out
$ Historic Options for sop decrypt

The sop decrypt option --verifications-out used to be named --verify-out. An implementation SHOULD accept either form of this option, and SHOULD produce a deprecation warning to standard error if the old form is used.

4.3.5. inline-detach: Split Signatures from an Inline-Signed Message

sop inline-detach [--no-armor] --signatures-out=SIGNATURES
  • Standard Input: INLINESIGNED

  • Standard Output: DATA (the message without any signatures)

In some contexts, the user may expect an inline-signed message of some form or another (INLINESIGNED, see Section 6.5) rather than a message and its detached signature. sop inline-detach takes such an inline-signed message on standard input, and splits it into:

  • the potentially signed material on standard output, and

  • a detached signature block to the destination identified by --signatures-out

Note that no cryptographic verification of the signatures is done by this subcommand. Once the inline-signed message is separated, verification of the detached signature can be done with sop verify.

If no --signatures-out is supplied, sop inline-detach fails with MISSING_ARG.

Note that there may be more than one Signature packet in an inline-signed message. All signatures found in the inline-signed message will be emitted to the --signatures-out destination.

If the inline-signed message uses the Cleartext Signature Framework, it may be dash-escaped (see Section 7.1 of [RFC4880]). The output of sop detach-inband-signature-and-message will have any dash-escaping removed.

If the input is not an INLINESIGNED message, sop inline-detach fails with BAD_DATA. If the input contains more than one object that could be interpreted as an INLINESIGNED message, sop inline-detach also fails with BAD_DATA. A sop implementation MAY accept (and discard) leading and trailing data when the incoming INLINESIGNED message uses the Cleartext Signature Framework.

If the file designated by --signatures-out already exists in the filesystem, sop detach-inband-signature-and-message will fail with OUTPUT_EXISTS.

Note that --no-armor here governs the data written to the --signatures-out destination. Standard output is always the raw message, not an OpenPGP packet.


$ sop inline-detach --signatures-out=Release.pgp < InRelease >Release
$ sop verify Release.pgp archive-keyring.pgp < Release

4.3.6. inline-verify: Verify an Inline-Signed Message

sop inline-verify [--not-before=DATE] [--not-after=DATE]
    [--] CERTS [CERTS...]

This command is similar to sop verify (Section 4.3.2) except that it takes an INLINESIGNED message (see Section 6.5) and produces the message body (without signatures) on standard output. It is also similar to sop inline-detach (Section 4.3.5) except that it actually performs signature verification.

--not-before and --not-after indicate that signatures with dates outside certain range MUST NOT be considered valid.

--not-before defaults to the beginning of time. Accepts the special value - to indicate the beginning of time (i.e., no lower boundary).

--not-after defaults to the current system time (now). Accepts the special value - to indicate the end of time (i.e., no upper boundary).

sop inline-verify only returns OK if INLINESIGNED contains at least one valid signature made during the time window specified by a certificate included in any CERTS object.

For details about the valid signatures, the user MUST inspect the VERIFICATIONS output.

If no CERTS are supplied, sop inline-verify fails with MISSING_ARG.

If no valid signatures are found, sop inline-verify fails with NO_SIGNATURE and emits nothing on standard output.

See Section 12.1 for more details about signature verification.


(In this example, we see signature verification succeed first, and then fail on a modified version of the message.)

$ sop inline-verify -- alice.pgp < message.txt
Hello, world!
$ echo $?
$ sed s/Hello/Goodbye/ < message.txt | sop inline-verify -- alice.pgp
$ echo $?

The inline-verify subcommand and all of its options are part of the sopv subset (see Section 3) starting at sopv version 1.0.

4.3.7. inline-sign: Create an Inline-Signed Message

sop inline-sign [--no-armor]
     [--] KEYS [KEYS...]

Exactly one signature will be made by each key in the supplied KEYS arguments.

The generated output stream will be an inline-signed message, by default producing an OpenPGP "Signed Message" packet stream.

--as defaults to binary. If --as= is set to either text or clearsigned, and the input DATA is not valid UTF-8 (Section 10.7), sop inline-sign fails with EXPECTED_TEXT.

--as=binary SHOULD result in OpenPGP signatures of type 0x00 ("Signature of a binary document"). --as=text SHOULD result in an OpenPGP signature of type 0x01 ("Signature of a canonical text document"). See Section 5.2.1 of [RFC4880] for more details. --as=clearsigned SHOULD behave the same way as --as=text except that it produces an output stream using the Cleartext Signature Framework (see Section 7 of [RFC4880] and Section 10.5).

If both --no-armor and --as=clearsigned are supplied, sop inline-sign fails with INCOMPATIBLE_OPTIONS.

If the signing key material in any key in the KEYS objects is password-protected, sop inline-sign SHOULD try all supplied --with-key-password options to unlock the key material until it finds one that enables the use of the key for signing. If none of the PASSWORD options unlock the key (or if no such option is supplied), sop inline-sign will fail with KEY_IS_PROTECTED. Note that PASSWORD is an indirect data type from which the actual password is acquired (Section 6). Note also the guidance for retrying variants of a non-human-readable password in Section 10.8.2.

If any key in the KEYS objects is not capable of producing a signature, sop inline-sign will fail with KEY_CANNOT_SIGN.

sop inline-sign MUST NOT produce any extra signatures beyond those from KEYS objects supplied on the command line.


$ sop inline-sign --as=clearsigned alice.sec < message.txt > message-signed.txt
$ head -n5 < message-signed.txt
Hash: SHA256

This is the message.

4.4. Transport Subcommands

The commands in this section handle manipulating OpenPGP objects for transport: armoring and dearmoring for 7-bit cleanness and compactness, respectively.

4.4.1. armor: Convert Binary to ASCII

sop armor

  • Standard Output: the same material with ASCII-armoring added, if not already present

sop armor inspects the input and chooses the label appropriately, based on the OpenPGP packets encountered. If the type of the first OpenPGP packet is:

  • 0x05 (Secret-Key), the packet stream should be parsed as a KEYS input (with Armor Header BEGIN PGP PRIVATE KEY BLOCK).

  • 0x06 (Public-Key), the packet stream should be parsed as a CERTS input (with Armor Header BEGIN PGP PUBLIC KEY BLOCK).

  • 0x01 (Public-key Encrypted Session Key) or 0x03 (Symmetric-key Encrypted Session Key), the packet stream should be parsed as a CIPHERTEXT input (with Armor Header BEGIN PGP MESSAGE).

  • 0x04 (One-Pass Signature), the packet stream should be parsed as an INLINESIGNED input (with Armor Header BEGIN PGP MESSAGE).

  • 0x02 (Signature), the packet stream may be either a SIGNATURES input or an INLINESIGNED input. If the packet stream contains only Signature packets, it should be parsed as aSIGNATURES input (with Armor Header BEGIN PGP SIGNATURE). If it contains any packet other than a Signature packet, it should be parsed as an INLINESIGNED input (with Armor Header BEGIN PGP MESSAGE).

If the input packet stream does not match any expected sequence of packet types, sop armor fails with BAD_DATA.

Since sop armor accepts ASCII-armored input as well as binary input, this operation is idempotent on well-structured data. A caller can use this subcommand blindly to ensure that any well-formed OpenPGP packet stream is 7-bit clean.

FIXME: what to do if the input is a CSF INLINESIGNED message? Three choices:

  • Leave it untouched -- this violates the claim about blindly ensuring 7-bit clean, since UTF-8-encoded message text is not necessarily 7-bit clean.

  • Convert to ASCII-armored INLINESIGNED -- this requires synthesis of OPS packet (from signatures block) and Literal Data packet (from the message body).

  • Raise a specific error.


$ sop armor < bob.bin > bob.pgp
$ head -n1 bob.pgp
$ Historic Options for sop armor

sop armor used to be specified as having a --label option, with an argument that took one of the following values: auto, sig, key, cert, or message, which allowed the user to specify the label used in the header and tail of the armoring.

The default value for --label was auto, which matches the currently specified behavior. This option is now deprecated, as it offers no useful functionality.

4.4.2. dearmor: Convert ASCII to Binary

sop dearmor

  • Standard Output: the same material with any ASCII-armoring removed

If the input packet stream does not match any of the expected sequence of packet types, sop dearmor fails with BAD_DATA. See also Section 10.4.

Since sop dearmor accepts binary-formatted input as well as ASCII-armored input, this operation is idempotent on well-structured data. A caller can use this subcommand blindly ensure that any well-formed OpenPGP packet stream is in its standard binary representation.

FIXME: what to do if the input is a CSF INLINESIGNED? Three choices:

  • Leave it untouched -- output data is not really in binary format.

  • Convert to binary-format INLINESIGNED -- this requires synthesis of OPS packet (from CSF Hash header) and Literal Data packet (from the message body).

  • Raise a specific error.


$ sop dearmor < message.txt.asc > message.txt.sig

5. Input String Types

Some material is passed to sop directly as a string on the command line.

5.1. DATE

An ISO-8601 formatted timestamp with time zone, or the special value now to indicate the current system time.


  • now

  • 2019-10-29T12:11:04+00:00

  • 2019-10-24T23:48:29Z

  • 20191029T121104Z

In some cases where used to specify lower and upper boundaries, a DATE value can be set to - to indicate "no time limit".

A flexible implementation of sop MAY accept date inputs in other unambiguous forms.

Note that whenever sop emits a timestamp (e.g., in Section 6.10) it MUST produce only a UTC-based ISO-8601 compliant representation with a resolution of one second, using the literal Z suffix to indicate timezone.


This is an arbitrary UTF-8 string (Section 10.7). By convention, most User IDs are of the form Display Name <>, but they do not need to be.

By internal policy, an implementation MAY reject a USERID if there are certain UTF-8 strings it declines to work with as a User ID. For example, an implementation may reject the empty string, or a string with characters in it that it considers problematic. Of course, refusing to create a particular User ID does not prevent an implementation from encountering such a User ID in its input.


This is an ASCII string that matches the name of one of the subcommands listed in Section 4.


Some sop subcommands can accept a --profile option, which takes as an argument the name of a profile.

A profile name is a UTF-8 string that has no whitespace in it.

Which profiles are available depends on the sop implementation.

Similar to OpenPGP Notation names, profile names are divided into two namespaces: the IETF namespace and the user namespace. A profile name in the user namespace ends with the @ character (0x40) followed by a DNS domain name. A profile name in the IETF namespace does not have an @ character.

A profile name in the user space is owned and controlled by the owner of the domain in the suffix. A sop implementation that implements a user profile but does not own the domain in question SHOULD hew as closely as possible to the semantics described by the owner of the domain.

A profile name in the IETF namespace that begins with the string rfc should have semantics that hew as closely as possible to the referenced RFC. Similarly, a profile name in the IETF namespace that begins with the string draft- should have semantics that hew as closely as possible to the referenced Internet Draft.

The reserved profile name default in the IETF namespace simply refers to the implementation's default choices. It is not mandatory to name the default profile default. The first profile listed in the list-profiles output is considered the default configuration, as specified in Section 6.12.

Note that this profile mechanism is intended to provide a limited way for an implementation to select among a small set of options that the implementer has vetted and is satisfied with. It is not intended to provide an arbitrary channel for complex configuration, and a sop implementation MUST NOT use it in that way.

6. Input/Output Indirect Types

Some material is passed to sop indirectly, typically by referring to a filename containing the data in question. This type of data may also be passed to sop on Standard Input, or delivered by sop to Standard Output.

If any input data is specified explicitly to be read from a file that does not exist, sop will fail with MISSING_INPUT.

If any input data does not meet the requirements described below, sop will fail with BAD_DATA.

6.1. Special Designators for Indirect Types

An indirect argument or parameter that starts with "@" (COMMERCIAL AT, U+0040) is not treated as a filename, but is reserved for special handling, based on the prefix that follows the @. We describe two of those prefixes (@ENV: and @FD:) here. A sop implementation that receives such a special designator but does not know how to handle a given prefix in that context MUST fail with UNSUPPORTED_SPECIAL_PREFIX.

See Section 10.9 for more details about safe handling of these special designators.

6.1.1. @ENV: Special Designator for Environment Variable

If the filename for any indirect material used as input has the special form @ENV:xxx, then contents of environment variable $xxx is used instead of looking in the filesystem. @ENV is for input only: if the prefix @ENV: is used for any output argument, sop fails with UNSUPPORTED_SPECIAL_PREFIX.

The sopv subset (see Section 3) MUST be capable of supporting the @ENV special designator for all relevant inputs starting at sopv version 1.0.

6.1.2. @FD: Special Designator for File Descriptor

If the filename for any indirect material used as either input or output has the special form @FD:nnn where nnn is a decimal integer, then the associated data is read from file descriptor nnn.

On platforms which support file descriptors, the sopv subset (see Section 3) MUST be capable of supporting the @FD special designator for all relevant inputs and outputs starting at sopv version 1.0.

6.2. CERTS

One or more OpenPGP certificates (Section 10.1 of [I-D.ietf-openpgp-crypto-refresh-10]), aka "Transferable Public Key". May be armored (see Section 10.4).

Although some existing workflows may prefer to use one CERTS object with multiple certificates in it (a "keyring"), supplying exactly one certificate per CERTS input will make error reporting clearer and easier.

If any CERTS input contains secret key material, sop MUST fail with BAD_DATA. This strictness is intended to keep the consumer of the sop interface clear about what material they are dealing with in what locations. This should reduce the consumer's risk of accidentally exposing secret key materal where they meant to expose a CERTS object.

6.3. KEYS

One or more OpenPGP Transferable Secret Keys (Section 10.2 of [I-D.ietf-openpgp-crypto-refresh-10]). May be armored (see Section 10.4).

Secret key material is often locked with a password to ensure that it cannot be simply copied and reused. If any secret key material is locked with a password and no --with-key-password option is supplied, sop may fail with error KEY_IS_PROTECTED. However, when a cleartext secret key (that is, one not locked with a password) is available, sop should always be able to use it, whether a --with-key-password option is supplied or not.

Although some existing workflows may prefer to use one KEYS object with multiple keys in it (a "secret keyring"), supplying exactly one key per KEYS input will make error reporting clearer and easier.


sop accepts only a restricted subset of the arbitrarily-nested grammar allowed by the OpenPGP Messages definition (Section 10.3 of [I-D.ietf-openpgp-crypto-refresh-10]).

In particular, it accepts and generates only:

An OpenPGP message, consisting of a sequence of PKESKs (Section 5.1 of [I-D.ietf-openpgp-crypto-refresh-10]) and SKESKs (Section 5.3 of [I-D.ietf-openpgp-crypto-refresh-10]), followed by one SEIPD (Section 5.13 of [I-D.ietf-openpgp-crypto-refresh-10]).

The SEIPD can decrypt into one of two things:

  • "Maybe Signed Data" (see below), or

  • Compressed data packet that contains "Maybe Signed Data"

"Maybe Signed Data" is a sequence of:

  • N (zero or more) one-pass signature packets, followed by

  • zero or more signature packets, followed by

  • one Literal data packet, followed by

  • N signature packets (corresponding to the outer one-pass signatures packets)

FIXME: does any tool do compression inside signing? Do we need to handle that?

May be armored (see Section 10.4).


An inline-signed message may take any one of three different forms:

The subset of the packet grammar expected in the first two forms consists of either:

  • a series of Signature packets followed by a Literal Data packet

  • a series of One-Pass Signature (OPS) packets, followed by one Literal Data packet, followed by an equal number of Signature packets corresponding to the OPS packets

When the message is in the third form (Cleartext Signature Framework), it has the following properties:

  • The stream SHOULD consist solely of UTF-8 text

  • Every Signature packet found in the stream SHOULD have Signature Type 0x01 (canonical text document).

  • It SHOULD NOT contain leading text (before the -----BEGIN PGP SIGNED MESSAGE----- cleartext header) or trailing text (after the -----END PGP SIGNATURE----- armor tail).

While some OpenPGP implementations MAY produce more complicated inline signed messages, a sop implementation SHOULD limit itself to producing these straightforward forms.


One or more OpenPGP Signature packets. May be armored (see Section 10.4).


This documentation uses the GnuPG defacto ASCII representation:


where ALGONUM is the decimal value associated with the OpenPGP Symmetric Key Algorithms (Section 9.3 of [I-D.ietf-openpgp-crypto-refresh-10]) and HEXKEY is the hexadecimal representation of the binary key.

Example AES-256 session key:


A sop implementation SHOULD produce session key data in this format. When consuming such a session key, sop SHOULD be willing to accept either upper or lower case hexadecimal digits, and to gracefully ignore any trailing whitespace.


This output-only type indicates the cryptographic digest used when making a signature. It is useful specifically when generating signed PGP/MIME objects, which want a micalg= parameter for the multipart/signed content type as described in Section 5 of [RFC3156].

It will typically be a string like pgp-sha512, but in some situations (multiple signatures using different digests) it will be the empty string. If the user of sop is assembling a PGP/MIME signed object, and the MICALG output is the empty string, the user should omit the micalg= parameter entirely.


This input-only is expected to be a UTF-8 string (Section 10.7), but for sop decrypt, any bytestring that the user supplies will be accepted. Note the details in sop encrypt and sop decrypt about trailing whitespace!

See also Section 10.8 for more discussion.


This output-only type consists of one line per successful signature verification. Each line has three structured fields delimited by a single space, followed by arbitrary text to the end of the line that forms a message describing the verification.

  • ISO-8601 UTC datestamp of the signature, to one second precision, using the Z suffix

  • Fingerprint of the signing key (may be a subkey)

  • Fingerprint of primary key of signing certificate (if signed by primary key, same as the previous field)

  • a string describing the mode of the signature, either mode:text or mode:binary

  • message describing the verification (free form)

Note that while Section 5.1 permits a sop implementation to accept other unambiguous date representations, its date output here MUST be a strict ISO-8601 UTC date timestamp. In particular:

  • the date and time fields MUST be separated by T, not by whitespace, since whitespace is used as a delimiter

  • the time MUST be emitted in UTC, with the explicit suffix Z

  • the time MUST be emitted with one-second precision


2019-10-24T23:48:29Z C90E6D36200A1B922A1509E77618196529AE5FF8 C4BC2DDB38CCE96485EBE9C2F20691179038E5C6 mode:binary certificate from dkg.asc

6.11. DATA

Cleartext, arbitrary data. This is either a bytestream or UTF-8 text.

It MUST only be UTF-8 text in the case of input supplied to sop sign --as=text or sop encrypt --as=text. If sop receives DATA containing non-UTF-8 octets in this case, it will fail (see Section 10.7) with EXPECTED_TEXT.


This output-only type consists of simple UTF-8 textual output, with one line per profile. Each line consists of the profile name optionally followed by a colon (0x31), a space (0x20), and a brief human-readable description of the intended semantics of the profile. Each line may be at most 1000 bytes, and no more than 4 profiles may be listed.

These limits are intended to force sop implementers to make hard decisions and to keep things simple.

The first profile MAY be explicitly named default. If it is not named default, then default is an alias for the first profile listed. No profile after the first listed may be named default.

See Section 5.4 for more discussion about the namespace and intended semantics of each profile.

7. Failure Modes

sop return codes have both mnemonics and numeric values.

When sop succeeds, it will return 0 (OK) and emit nothing to Standard Error. When sop fails, it fails with a non-zero return code, and emits one or more warning messages on Standard Error. Known return codes include:

Table 1: Error return codes
Value Mnemonic Meaning
0 OK Success
3 NO_SIGNATURE No acceptable signatures found (sop verify)
13 UNSUPPORTED_ASYMMETRIC_ALGO Asymmetric algorithm unsupported (sop encrypt)
17 CERT_CANNOT_ENCRYPT Certificate not encryption-capable (e.g., expired, revoked, unacceptable usage flags) (sop encrypt)
19 MISSING_ARG Missing required argument
23 INCOMPLETE_VERIFICATION Incomplete verification instructions (sop decrypt)
29 CANNOT_DECRYPT Unable to decrypt (sop decrypt)
31 PASSWORD_NOT_HUMAN_READABLE Non-UTF-8 or otherwise unreliable password (sop encrypt, sop generate-key)
37 UNSUPPORTED_OPTION Unsupported option
41 BAD_DATA Invalid data type (no secret key where KEYS expected, secret key where CERTS expected, etc)
53 EXPECTED_TEXT Non-text input where text expected
59 OUTPUT_EXISTS Output file already exists
61 MISSING_INPUT Input file does not exist
67 KEY_IS_PROTECTED A KEYS input is password-protected (locked), and sop cannot unlock it with any of the --with-key-password (or --old-key-password) options
69 UNSUPPORTED_SUBCOMMAND Unsupported subcommand
71 UNSUPPORTED_SPECIAL_PREFIX An indirect parameter is a special designator (it starts with @) but sop does not know how to handle the prefix
73 AMBIGUOUS_INPUT A indirect input parameter is a special designator (it starts with @), and a filename matching the designator is actually present
79 KEY_CANNOT_SIGN Key not signature-capable (e.g., expired, revoked, unacceptable usage flags) (sop sign and sop encrypt with --sign-with)
83 INCOMPATIBLE_OPTIONS Options were supplied that are incompatible with each other
89 UNSUPPORTED_PROFILE The requested profile is unsupported (sop generate-key, sop encrypt), or the indicated subcommand does not accept profiles (sop list-profiles)
97 NO_HARDWARE_KEY_FOUND The sop implementation supports some form of hardware-backed secret keys, but could not identify the hardware device (see Section 10.10)
101 HARDWARE_KEY_FAILURE The sop implementation tried to use a hardware-backed secret key, but the cryptographic hardware refused the operation for some reason other than a bad PIN or password (see Section 10.10)

If a sop implementation fails in some way not contemplated by this document, it MAY return any non-zero error code, not only those listed above.

8. Known Implementations

The following implementations are known at the time of this draft:

Table 2: Known implementations
Project name URL cli name notes
Sequoia SOP sqop Implemented in Rust using the sequoia-openpgp crate
gosop gosop Implemented in golang (Go) using GOpenPGP
PGPainless SOP pgpainless-cli Implemented in Java using PGPainless
sopgpy sopgpy Implemented in Python using PGPy
sop-openpgp.js sop-openpgp Implemented in JavaScript using OpenPGP.js
gpgme-sop gpgme-sop A Rust wrapper around the gpgme C library
RNP-sop rnp-sop A Rust wrapper around the librnp C library
dkg-sop dkg-sop Implemented in C++ using the LibTMCG library

9. Alternate Interfaces

This draft primarily defines a command line interface, but future versions may try to outline a comparable idiomatic interface for C or some other widely-used programming language.

Comparable idiomatic interfaces are already active in the wild for different programming languages, in particular:

These programmatic interfaces are typically coupled with a wrapper that can automatically generate a command-line tool compatible with this draft.

An implementation that uses one of these languages should target the corresponding idiomatic interface for ease of development and interoperability.

10. Guidance for Implementers

sop uses a few assumptions that implementers might want to consider.

10.1. One OpenPGP Message at a Time

sop is intended to be a simple tool that operates on one OpenPGP object at a time. It should be composable, if you want to use it to deal with multiple OpenPGP objects.

FIXME: discuss what this means for streaming. The stdio interface doesn't necessarily imply streamed output.

10.2. Simplified Subset of OpenPGP Message

While the formal grammar for OpenPGP Message is arbitrarily nestable, sop constrains itself to what it sees as a single "layer" (see Section 6.4).

This is a deliberate choice, because it is what most consumers expect. Also, if an arbitrarily-nested structure is parsed with a recursive algorithm, this risks a denial of service vulnerability. sop intends to be implementable with a parser that defensively declines to do recursive descent into an OpenPGP Message.

Note that an implementation of sop decrypt MAY choose to handle more complex structures, but if it does, it should document the other structures it handles and why it chooses to do so. We can use such documentation to improve future versions of this spec.

10.3. Validate Signatures Only from Known Signers

There are generally only a few signers who are relevant for a given OpenPGP message. When verifying signatures, sop expects that the caller can identify those relevant signers ahead of time.

10.4. OpenPGP Inputs can be either Binary or ASCII-armored

OpenPGP material on input can be in either ASCII-armored or binary form. This is a deliberate choice because there are typical scenarios where the program can't predict which form will appear. Expecting the caller of sop to detect the form and adjust accordingly seems both redundant and error-prone.

The simple way to detect possible ASCII-armoring is to see whether the high bit of the first octet is set: Section 4.2 of [RFC4880] indicates that bit 7 is always one in the first octet of an OpenPGP packet. In standard ASCII-armor, the first character is "-" (HYPHEN-MINUS, U+002D), so the high bit should be cleared.

When considering an input as ASCII-armored OpenPGP material, sop MAY reject an input based on any of the following variations (see Section 6.2 of [RFC4880] for precise definitions):

  • An unknown Armor Header Line

  • Any text before the Armor Header Line

  • Malformed lines in the Armor Headers section

  • Any non-whitespace data after the Armor Tail

  • Any Radix-64 encoded line with more than 76 characters

  • Invalid characters in the Radix-64-encoded data

  • An invalid Armor Checksum

  • A mismatch between the Armor Header Line and the Armor Tail

  • More than one ASCII-armored object in the input

For robustness, sop SHOULD be willing to ignore whitespace after the Armor Tail.

For any plural data type (i.e.,SIGNATURES, CERTS, or KEYS), the unarmored form is trivially concatenatable with another object of the same type (e.g., with Unix's cat utility). But the armored forms are not concatenatable without first dearmoring. To avoid inconsistent behavior, a sop implementation SHOULD reject anything that appears to be a concatenated series of ASCII-armored objects.

When considering OpenPGP material as input, regardless of whether it is ASCII-armored or binary, sop SHOULD reject any material that doesn't produce a valid stream of OpenPGP packets. For example, sop SHOULD raise an error if an OpenPGP packet header is malformed, or if there is trailing garbage after the end of a packet.

For a given type of OpenPGP input material (i.e., SIGNATURES, CERTS, KEYS, INLINESIGNED, or CIPHERTEXT), sop SHOULD also reject any input that does not conform to the expected packet stream. See Section 6 for the expected packet stream for different types.

10.5. Complexities of the Cleartext Signature Framework

sop prefers a detached signature as the baseline form of OpenPGP signature, but provides affordances for dealing with inline-signed messages (see INLINESIGNED, Section 6.5) as well.

The most complex form of inline-signed messages is the Cleartext Signature Framework (CSF). Handling the CSF structure requires parsing to delimit the multiple parts of the document, including at least:

  • any preamble before the message

  • the inline message header (delimiter line, OpenPGP headers)

  • the message itself

  • the divider between the message and the signature (including any OpenPGP headers there)

  • the signature

  • the divider that terminates the signature

  • any suffix after the signature

Note also that the preamble or the suffix might be arbitrary text, and might themselves contain OpenPGP messages (whether signatures or otherwise).

If the parser that does this split differs in any way from the parser that does the verification, or parts of the message are confused, it would be possible to produce a verification status and an actual signed message that don't correspond to one another.

Blurred boundary problems like this can produce ugly attacks similar to those found in [EFAIL].

A user of sop that receives an inline-signed message (whether the message uses the CSF or not) can detach the signature from the message with sop inline-detach (see Section 4.3.5).

Alternately, the user can send the message through sop inline-verify to confirm required signatures, and then (if signatures are valid) supply its output to the consumer of the signed message.

10.6. Reliance on Supplied Certs and Keys

A truly stateless implementation may find that it spends more time validating the internal consistency of certificates and keys than it does on the actual object security operations.

For performance reasons, an implementation may choose to ignore validation on certificate and key material supplied to it. The security implications of doing so depend on how the certs and keys are managed outside of sop.

10.7. Text is always UTF-8

Various places in this specification require UTF-8 [RFC3629] when encoding text. sop implementations SHOULD NOT consider textual data in any other character encoding.

OpenPGP Implementations MUST already handle UTF-8, because various parts of [RFC4880] require it, including:

  • User ID

  • Notation name

  • Reason for revocation

  • ASCII-armor Comment: header

Dealing with messages in other charsets leads to weird security failures like [Charset-Switching], especially when the charset indication is not covered by any sort of cryptographic integrity check. Restricting textual data to UTF-8 universally across the OpenPGP ecosystem eliminates any such risk without losing functionality, since UTF-8 can encode all known characters.

10.8. Passwords are Human-Readable

Passwords are generally expected to be human-readable, as they are typically recorded and transmitted as human-visible, human-transferable strings. However, they are used in the OpenPGP protocol as bytestrings, so it is important to ensure that there is a reliable bidirectional mapping between strings and bytes. The maximally robust behavior here is for sop encrypt and sop generate-key (that is, commands that use a password to encrypt) to constrain the choice of passwords to strings that have such a mapping, and for sop decrypt and sop sign (and sop inline-sign, as well assop encrypt when decrypting a signing key; that is, commands that use a password to decrypt) to try multiple plausible versions of any password supplied by PASSWORD.

10.8.1. Generating Material with Human-Readable Passwords

When generating material based on a password, sop encrypt and sop generate-key enforce that the password is actually meaningfully human-transferable. In particular, an implementation generating material based on a new paasword SHOULD apply the following considerations to the supplied password:

  • require UTF-8

  • trim trailing whitespace

Some sop encrypt and sop generate-key implementations may make even more strict requirements on input to ensure that they are transferable between humans in a robust way.

For example, a more strict sop encrypt or sop generate-key MAY also:

  • forbid leading whitespace

  • forbid non-printing characters other than SPACE (U+0020), such as ZERO WIDTH NON-JOINER (U+200C) or TAB (U+0009)

  • require the password to be in Unicode Normal Form C ([UNICODE-NORMALIZATION])

Violations of these more-strict policies SHOULD result in an error of PASSWORD_NOT_HUMAN_READABLE.

A sop encrypt or sop generate-key implementation typically SHOULD NOT attempt enforce a minimum "password strength", but in the event that some implementation does, it MUST NOT represent a weak password with PASSWORD_NOT_HUMAN_READABLE.

10.8.2. Consuming Password-protected Material

When sop decrypt receives a PASSWORD input, either from a --with-key-password or --with-password option, it sees its content as a bytestring. sop sign also sees the content of any PASSWORD input supplied to its --with-key-password option as a bytestring. If the bytestring fails to work as a password, but ends in UTF-8 whitespace, it will try again with the trailing whitespace removed. This handles a common pattern of using a file with a final newline, for example. The pattern here is one of robustness in the face of typical errors in human-transferred textual data.

A more robust sop decrypt or sop sign implementation that finds neither of the above two attempts work for a given PASSWORD MAY try additional variations if they produce a different bytestring, such as:

  • trimming any leading whitespace, if discovered

  • trimming any internal non-printable characters other than SPACE (U+0020)

  • converting the supplied PASSWORD into Unicode Normal Form C ([UNICODE-NORMALIZATION])

A sop decrypt or sop sign implementation that stages multiple decryption attempts like this SHOULD consider the computational resources consumed by each attempt, to avoid presenting an attack surface for resource exhaustion in the face of a non-standard PASSWORD input.

10.9. Be Careful with Special Designators

As documented in Section 6.1, special designators for indirect inputs like @ENV: and @FD: (and indirect outputs using @FD:) warrant some special/cautious handling.

For one thing, it's conceivable that the filesystem could contain a file with these literal names. If sop receives an indirect output parameter that starts with an "@" (COMMERCIAL AT, U+0040) it MUST NOT write to the filesystem for that parameter. A sop implementation that receives such a parameter as input MAY test for the presence of such a file in the filesystem and fail with AMBIGUOUS_INPUT to warn the user of the ambiguity and possible confusion.

These special designators are likely to be used to pass sensitive data (like secret key material or passwords) so that it doesn't need to touch the filesystem. Given this sensitivity, sop should be careful with such an input, and minimize its leakage to other processes. In particular, sop SHOULD NOT leak any environment variable identified by @ENV: or file descriptor identified by @FD: to any subprocess unless the subprocess specifically needs access to that data.

10.10. Nuances for Hardware-backed Secret Key Material

There are a number of limitations and nuances to be aware of for hardware-backed secret key support in this interface. Some sop implementations will simply not support hardware-backed secret key material. Other implementations might support only a single kind of hardware-backing (e.g., an OpenPGP Smartcard [OPENPGP-SMARTCARD] but not a TPM, or vice versa).

There is no formally adopted OpenPGP standard for identifying that a given secret key is backed by hardware based on the OpenPGP wire format. [I-D.dkg-openpgp-hardware-secrets] proposes one simple and straightforward approach for how the wire format could cover this use case. This simple mechanism is deliberately agnostic about the specific kind of cryptographic hardware, but it does imply a sort of rough shape of what the interface to the hardware would permit. In particular, it will work best with hardware that has the following properties:

  • The hardware does specific asymmetric secret key operations, using secret keys that it does not release.

  • The user can ask the hardware to provide a list of corresponding public key material (or OpenPGP key fingerprints) for any of the secret keys held by the device.

  • The hardware MAY require the provision of a PIN or password to enable secret key operation, but does not require a PIN or password for the list of public key material.

The sop interface does not currently provide for provisioning cryptographic hardware with secret key material, or for changing the PIN or password for the cryptographic hardware. Users of cryptographic hardware need to do provisioning and PIN or password setting outside of sop.

If a user has two attached hardware tokens that both hold the same secret key, and they are both password-locked, and they use different passwords, sop offers no way for the user to clearly indicate which password belongs to which device. Some cryptographic hardware is designed to lock the device if the wrong password is entered too many times, so users in this configuration are at risk of accidental lockout. The easiest resolution for this is for the user to detach any duplicate devices before invoking sop.

Note that some OpenPGP implementations use the private codepoint ranges in the OpenPGP specification within an OpenPGP Transferable Secret Key (e.g., [GNUPG-SECRET-STUB]) to indicate that the secret key can be found on a smartcard.

While hardware-backed secret key operations can be significantly slower than modern computers, and physical affordances like button-presses or NFC tapping can themselves incur delay, it's bad form for an invocation of sop to hang forever. This specification doesn't define a specific maximum allowable delay, but if an implementation calls into a hardware device either for public key listing or for secret key operations, it should not allow the cryptographic hardware to take an arbitrary amount of time to respond.

11. Guidance for Consumers

While sop is originally conceived of as an interface for interoperability testing, it's conceivable that an application that uses OpenPGP for object security would want to use it.

FIXME: more guidance for how to use such a tool safely and efficiently goes here.

FIXME: if an encrypted OpenPGP message arrives without metadata, it is difficult to know which signers to consider when decrypting. How do we do this efficiently without invoking sop decrypt twice, once without --verify-* and again with the expected identity material?

11.1. Choosing Between --as=text and --as=binary

A program that invokes sop to generate an OpenPGP signature typically needs to decide whether it is making a text or binary signature.

By default, sop will make a binary signature. The caller of sop sign should choose --as=text only when it knows that:

  • the data being signed is in fact textual, and encoded in UTF-8, and

  • the signed data might be transmitted to the recipient (the verifier of the signature) over a channel that has the propensity to transform line-endings.

Examples of such channels include FTP ([RFC0959]) and SMTP ([RFC5321]).

11.2. Special Designators and Unusual Filenames

In some cases, a user of sop might want to pass all the files in a given directory as positional parameters (e.g., a list of CERTS files to test a signature against).

If one of the files has a name that starts with --, it might be confused by sop for an option. If one of the files has a name that starts with @, it might be confused by sop as a special designator (Section 6.1).

If the user wants to deliberately refer to such an ambiguously-named file in the filesystem, they should prefix the filename with ./ or use an absolute path.

Any specific @FD: special designator SHOULD NOT be supplied more than once to an invocation of sop. If a sop invocation sees multiple copies of a specific @FD:n input (e.g., sop sign @FD:3 @FD:3), it MAY fail with MISSING_INPUT even if file descriptor 3 contains a valid KEYS, because the bytestream for the KEYS was consumed by the first argument. Doubling up on the same @FD: for output (e.g., sop decrypt --session-key-out=@FD:3 --verifications-out=@FD:3) also results in an ambiguous data stream.

12. Security Considerations

The OpenPGP object security model is typically used for confidentiality and authenticity purposes.

12.1. Signature Verification

In many contexts, an OpenPGP signature is verified to prove the origin and integrity of an underlying object.

When sop checks a signature over data (e.g., via sop verify or sop decrypt --verify-with), it MUST NOT consider it to be verified unless all of these conditions are met:

  • The signature must be made by a signing-capable public key that is present in one of the supplied certificates

  • The certificate and signing subkey must have been created before or at the signature time

  • The certificate and signing subkey must not have been expired at the signature time

  • The certificate and signing subkey must not be revoked with a "hard" revocation

  • If the certificate or signing subkey is revoked with a "soft" revocation, then the signature time must predate the revocation

  • The signing subkey must be properly bound to the primary key, and cross-signed

  • The signature (and any dependent signature, such as the cross-sig or subkey binding signatures) must be made with strong cryptographic algorithms (e.g., not MD5 or a 1024-bit RSA key)

  • The signature must be of type 0x00 ("Signature of a binary document") or 0x01 ("Signature of a canonical text document"); other signature types are inappropriate for data signatures

Implementers MAY also consider other factors in addition to the origin and authenticity, including application-specific information.

For example, consider the application domain of checking software updates. If software package Foo version 13.3.2 was signed on 2019-10-04, and the user receives a copy of Foo version 12.4.8 that was signed on 2019-10-16, it may be authentic and have a more recent signature date. But it is not an upgrade (12.4.8 < 13.3.2), and therefore it should not be applied automatically.

In such cases, it is critical that the application confirms that the other information verified is also protected by the relevant OpenPGP signature.

Signature validity is a complex topic (see for example the discussion at [DISPLAYING-SIGNATURES]), and this documentation cannot list all possible details.

12.2. Compression

The interface as currently specified does not allow for control of compression. Compressing and encrypting data that may contain both attacker-supplied material and sensitive material could leak information about the sensitive material (see the CRIME attack).

Unless an application knows for sure that no attacker-supplied material is present in the input, it should not compress during encryption.

13. Privacy Considerations

Material produced by sop encrypt may be placed on an untrusted machine (e.g., sent through the public SMTP network). That material may contain metadata that leaks associational information (e.g., recipient identifiers in PKESK packets (Section 5.1 of [I-D.ietf-openpgp-crypto-refresh-10])). FIXME: document things like PURBs and --hidden-recipient)

13.1. Object Security vs. Transport Security

OpenPGP offers an object security model, but says little to nothing about how the secured objects get to the relevant parties.

When sending or receiving OpenPGP material, the implementer should consider what privacy leakage is implicit with the transport.

14. References

14.1. Normative References

Wouters, P., Huigens, D., Winter, J., and N. Yutaka, "OpenPGP", Work in Progress, Internet-Draft, draft-ietf-openpgp-crypto-refresh-10, , <>.
Bradner, S., "Key words for use in RFCs to Indicate Requirement Levels", BCP 14, RFC 2119, DOI 10.17487/RFC2119, , <>.
Elkins, M., Del Torto, D., Levien, R., and T. Roessler, "MIME Security with OpenPGP", RFC 3156, DOI 10.17487/RFC3156, , <>.
Yergeau, F., "UTF-8, a transformation format of ISO 10646", STD 63, RFC 3629, DOI 10.17487/RFC3629, , <>.
Callas, J., Donnerhacke, L., Finney, H., Shaw, D., and R. Thayer, "OpenPGP Message Format", RFC 4880, DOI 10.17487/RFC4880, , <>.
Leiba, B., "Ambiguity of Uppercase vs Lowercase in RFC 2119 Key Words", BCP 14, RFC 8174, DOI 10.17487/RFC8174, , <>.

14.2. Informative References

Gillmor, D. K., "Inline PGP Considered Harmful", , <>.
Brunschwig, P., "On Displaying Signatures", n.d., <>.
Poddebniak, D. and C. Dresen, "Efail: Breaking S/MIME and OpenPGP Email Encryption using Exfiltration Channels", n.d., <>.
Koch, W., "GNU Extensions to the S2K algorithm", , <;gnupg-2.4.3$1511>.
Gillmor, D. K., "OpenPGP Hardware-Backed Secret Keys", Work in Progress, Internet-Draft, draft-dkg-openpgp-hardware-secrets-00, , <>.
Einarsson, B. R., "juga", and D. K. Gillmor, "OpenPGP Example Keys and Certificates", Work in Progress, Internet-Draft, draft-bre-openpgp-samples-01, , <>.
Gillmor, D. K., Hoeneisen, B., and A. Melnikov, "Guidance on End-to-End E-mail Security", Work in Progress, Internet-Draft, draft-ietf-lamps-e2e-mail-guidance-11, , <>.
"OpenPGP Interoperability Test Suite", , <>.
Pietig, A., "Functional Specification of the OpenPGP application on ISO Smart Card Operating Systems, Version 3.4", , <>.
Gillmor, D., "SOP for python", n.d., <>.
Postel, J. and J. Reynolds, "File Transfer Protocol", STD 9, RFC 959, DOI 10.17487/RFC0959, , <>.
Klensin, J., "Simple Mail Transfer Protocol", RFC 5321, DOI 10.17487/RFC5321, , <>.
Winter, J., "A Rust implementation of the Stateless OpenPGP Protocol", n.d., <>.
Preston-Werner, T., "Semantic Versioning 2.0.0", , <>.
Schaub, P., "Stateless OpenPGP Protocol for Java.", n.d., <>.
Whistler, K., "Unicode Normalization Forms", , <>.

Appendix A. C Library API (Tentative)

As specified in this draft, SOP is a command-line tool.

However, it can also be useful to have a comparable API exposed as a C library. This library can be implemented as a shared object (e.g., .so, .dll, or .dylib depending on the platform) or as a statically linked object. This interface can be reused in many different places, as most modern programming languages offer "bindings" to C libraries.

A proposed interface to a C library follows here as a C header file.

The primary goal of this shared object interface is to make it easy to implement the command-line interface described in this document. That said, it is also intended to be relatively ergonomic to use in plausible OpenPGP workflows where the caller has access to all of the explicit state.

If there is a plausible OpenPGP workflow that is not supported by this library API, please propose improvements and explain the specific workflow.

#ifndef __SOP_H__
#define __SOP_H__

#include <stdlib.h>
#include <stdint.h>
#include <stdbool.h>
#include <string.h>
#include <limits.h>

/* C API for Stateless OpenPGP */

/* Depends on C99 */

/* statically-defined, non-opaque definitions */

typedef enum {
  SOP_OK = 0,
  SOP_INTERNAL_ERROR = 1, /* Not part of sop CLI */
  SOP_INVALID_ARG = 2, /* Not part of sop CLI */
  SOP_OPERATION_ALREADY_EXECUTED = 4, /* Not part of sop CLI */
  SOP_BAD_DATA = 41,

  /* ensures a stable size for the enum -- do not use! */
} sop_err;

typedef enum {

  /* ensures a stable size for the enum -- do not use! */
} sop_sign_as;

typedef enum {

  /* ensures a stable size for the enum -- do not use! */
} sop_inline_sign_as;

typedef enum {

  /* ensures a stable size for the enum -- do not use! */
} sop_encrypt_as;

/* FIXME: timestamps */
/* time_t is 32-bit on some architectures; we also want this to be
   able to represent a "none" value as well as a "now" value without
   removing some value from the range of time_t */
typedef time_t sop_time;
#define sop_time_none ((sop_time)0)
#define sop_time_now ((sop_time)-1)

/* Context object
 * Each SOP object is bound back to a context object, and, when used
 * in combination with other SOP objects, all SOP objects should come
 * from the same context.
 * A SOP context object need not be thread-safe; it should probably
 * not be used across multiple threads.  See "Zero global state" in

struct sop_ctx_st;
typedef struct sop_ctx_st sop_ctx;

sop_ctx_new ();
sop_ctx_free (sop_ctx *sop);

/* Logging: */

typedef enum {

  /* ensures a stable size for the enum -- do not use! */
} sop_log_level;

static inline const char *
sop_log_level_name (sop_log_level log_level) {
#define rep(x) if (log_level == SOP_LOG_ ## x) return #x
#undef rep
  return "Unknown";

/* Handle warnings and other feedback.
 * A SOP implementation that is capable of producing log messages will
 * invoke the requested function with the log level of the message,
 * and a NULL-terminated UTF-8 human-readable string with no trailing
 * whitespace.
 * the "passthrough" pointer is supplied by the library user via
 * sop_set_log_level.
typedef void (*sop_log_func) (sop_log_level log_level, void *passthrough, const char *);
sop_set_log_function (sop_ctx *sop, sop_log_func func, void *passthrough);
/* Set the logging verbosity.
 * Only log warnings up to max_level. (by default, max_level is
 * suppressed).
sop_set_log_level (sop_ctx *sop, sop_log_level max_level);

/* Information about the library: */

/* The name and version of the implementation of the C API (simple
 * NUL-terminated string, no newlines), or NULL if there is an error
 * producing the version. */
const char *
sop_version (sop_ctx *sop);
/* The name and version of the primary underlying OpenPGP toolkit (or
 * NULL if there is no backend, or if there was an error producing the
 * backend version) */
const char *
sop_version_backend (sop_ctx *sop);
/* Any arbitrary extended version information other than sop_ctx_version.
   Version info should be UTF-8 text, separated by newlines (a
   NUL-terminated string, no trailing newline).  Can return NULL if
   there is nothing more to report beyond sop_version. */
const char *
sop_version_extended (sop_ctx *sop);

/* note: there is nothing comparable to sop version --sop-spec because
 * that should be visible based on the exported symbols in the shared
 * object */

/* PROFILE objects: */

/* These describe a profile (e.g. for generate-key or encrypt).  This
 * use used when the implementation might legitimately want to offer
 * the user some minimal amount of control over what is done.  The
 * profile-listing functions return blocks of four profiles.  A
 * sop_profile value of NULL represents no profile at all.  In a list
 * of sop_profile objects, once a NULL profile appears, no non-NULL
 * profiles may follow.

struct sop_profile_st;
typedef struct sop_profile_st sop_profile;
/* the NUL-terminated string returned by sop_profile_name MUST be a
   UTF-8 encoded string, and MUST NOT include any whitespace or colon
   (`:`) characters.  It MUST NOT vary depending on locale. */
const char *
sop_profile_name (const sop_profile *profile);
/* The NUL-terminated string returned by sop_profile_description
   cannot contain any newlines, and it MAY vary depending on
   locale(7) if the implementation is internationalized. */
const char *
sop_profile_description (const sop_profile *profile);


typedef struct {
  sop_profile *profile[SOP_MAX_PROFILE_COUNT];
} sop_profiles;

static inline int
sop_profiles_count(const sop_profiles profiles) {
  for (int i = 0; i < SOP_MAX_PROFILE_COUNT; i++)
    if (profiles.profile[i] == NULL)
      return i;

/* Return a list of profiles supported by the library for generating
 * keys.
sop_list_profiles_generate_key (sop_ctx *sop, sop_profiles *out);

/* CLEARTEXT (and other raw data): */

/* This is a standard buffer for bytestrings produced by sop.  Users
   never create this kind of object, but it is sometimes returned from
   the library. */
struct sop_buf_st;
typedef struct sop_buf_st sop_buf;

sop_buf_free (sop_buf *buf);
sop_buf_size (const sop_buf *buf);
const uint8_t *
sop_buf_data (const sop_buf *buf);

/* KEYS objects: */
struct sop_keys_st;
typedef struct sop_keys_st sop_keys;

sop_keys_from_bytes (sop_ctx *sop,
                     const uint8_t* data, size_t len,
                     sop_keys **out);
sop_keys_to_bytes (const sop_keys *keys,
                   bool armor, sop_buf **out);
sop_keys_free (sop_keys *keys);

/* Generate a new, minimal OpenPGP Transferable secret key.  `profile`
   can be NULL to mean the default profile. */
sop_generate_key_with_profile (sop_ctx *sop,
                               sop_profile *profile,
                               bool sign_only,
                               sop_keys **out);

static inline sop_err
sop_generate_key (sop_ctx *sop, sop_keys **out) {
  return sop_generate_key_with_profile (sop, NULL, false, out);

/* For each key in the sop_keys object, add the given user ID, and
   return a new sop_keys object containing the updated keys.  If the
   supplied user ID is not valid UTF-8 text, this call will fail and

   If the implementation rejects the user ID string by policy for any
   other reason, this call will fail and return SOP_BAD_DATA.
sop_keys_add_uid (const sop_keys *keys, const char *uid, sop_keys **out);

/* returns true if any of the secret key material is currently locked
   with a password */
sop_keys_locked (const sop_keys *keys, bool *out);

/* return a new sop_keys object with any secret key material encrypted
   with `password` unlocked, Returns SOP_OK if all keys have now been

   If any locked key material could not be unlocked, return
   SOP_KEY_IS_PROTECTED, while also unlocking what key material can be

   This allows the user to try an arbitrary bytestream as a password.
   Most users will just invoke the inlined sop_keys_unlock, below.

   An implementation MUST NOT reject proposed passwords by policy
   during unlock, but rather should try them as requested.
sop_keys_unlock_raw (const sop_keys *keys,
                     const uint8_t *raw_password, size_t len,
                     sop_keys **out);

static inline sop_err
sop_keys_unlock (const sop_keys *keys, const char *password, sop_keys **out) {
  return sop_keys_unlock_raw (keys,
                              (const uint8_t *)password,
                              strlen (password),

/* return a new sop_keys object where all secret key material is
   locked with `password` where possible.

   During locking, a safety-oriented implementation MAY reject the
   supplied password by policy for any number of reasons.  This helps
   libsop ensure that the proposed password can be successfully
   re-supplied during some future unlock attempt.

   If the implementation requires passwords to be UTF-8 text and the
   supplied password is not valid UTF-8, the implementation will fail,
   returning SOP_EXPECTED_TEXT.  If an implementation rejects a
   supplied password for some other reason (for example, if it
   contains an NUL, unprintable, or otherwise forbidden character),
   this call will fail and return SOP_BAD_DATA.

   If any key material is already locked, it does nothing and returns

   Upon a successful locking, the user probably wants to use
   sop_keys_free to free the original keys object.
sop_keys_lock_raw (const sop_keys *keys,
                   const uint8_t *password, size_t len,
                   sop_keys **out);

static inline sop_err
sop_keys_lock (const sop_keys *keys, const char *password, sop_keys **out) {
  return sop_keys_lock_raw (keys,
                            (const uint8_t *)password,
                            strlen (password),

/* CERTS objects: */
struct sop_certs_st;
typedef struct sop_certs_st sop_certs;

sop_certs_from_bytes (sop_ctx *sop,
                      const uint8_t* data, size_t len,
                      sop_certs **out);
sop_certs_to_bytes (const sop_certs *certs,
                    bool armor, sop_buf **out);
sop_certs_free (sop_certs *certs);

/* Return the OpenPGP certificates ("Transferable Public Keys") that
   correspond to the OpenPGP Transferable Secret Keys. */
sop_keys_extract_certs (const sop_keys *keys, sop_certs **out);

/* Return an OpenPGP revocation certificate for each Transferable
   Secret Key found in the input. */
sop_keys_revoke_keys (const sop_keys *keys, sop_certs **out);

/* SIGNATURES objects: */
struct sop_sigs_st;
typedef struct sop_sigs_st sop_sigs;

sop_sigs_from_bytes (sop_ctx *sop,
                     const uint8_t* data, size_t len,
                     sop_sigs **out);
sop_sigs_to_bytes (const sop_sigs *sigs,
                   bool armor, sop_buf **out);
sop_sigs_free (sop_sigs *sigs);

/* VERIFICATIONS (output only, describes valid, verified signatures): */
struct sop_verifications_st;
typedef struct sop_verifications_st sop_verifications;

sop_verifications_free (sop_verifications *verifs);
sop_verifications_count (const sop_verifications *verifs, int *out);
/* textual representations of verifications, in the form described by
sop_verifications_to_text (const sop_verifications *verifs,
                           sop_buf **out);
/* returns SOP_INTERNAL_ERROR if count is out of bounds. */
sop_verifications_get_time (const sop_verifications *verifs,
                            int count, sop_time *out);
/* returns SOP_INTERNAL_ERROR if count is out of bounds.  If the
   signature is neither type 0x00 nor 0x01, this should probably not
   be considered a valid, verified signature. */
sop_verifications_get_mode (const sop_verifications *verifs,
                            int count, sop_sign_as *out);

/* FIXME: (do we want to get more detailed info programmatically?
   each verification should also have an issuing key fingerprint, a
   primary key fingerprint, and a trailing text string) */

/* create detached signatures: */
struct sop_op_sign_st;
typedef struct sop_op_sign_st sop_op_sign;

sop_op_sign_new (sop_ctx *sop, sop_op_sign** out);
sop_op_sign_free (sop_op_sign *sign);

sop_op_sign_use_keys (sop_op_sign *sign, const sop_keys *keys);

sop_op_sign_detached_execute (sop_op_sign *sign,
                              sop_sign_as sign_as,
                              const uint8_t *msg,
                              size_t sz,
                              sop_buf **micalg_out,
                              sop_sigs **out);

/* verify detached signatures: */
struct sop_op_verify_st;
typedef struct sop_op_verify_st sop_op_verify;

sop_op_verify_new (sop_ctx *sop, sop_op_verify** out);
sop_op_verify_free (sop_op_verify *verify);

sop_op_verify_not_before (sop_op_verify *verify, sop_time when);
sop_op_verify_not_after (sop_op_verify *verify, sop_time when);
sop_op_verify_add_signers (sop_op_verify *verify,
                           const sop_certs *signers);

/* if no verifications are possible with the set of signers, this
   returns SOP_NO_SIGNATURE, and *out is set to NULL */
sop_op_verify_detached_execute (sop_op_verify *verify,
                                const sop_sigs *sigs,
                                const uint8_t *msg,
                                size_t sz,
                                sop_verifications **out);

/* INLINESIGNED object: */
struct sop_inlinesigned_st;
typedef struct sop_inlinesigned_st sop_inlinesigned;

sop_inlinesigned_from_bytes (sop_ctx *sop,
                             const uint8_t* data, size_t len,
                             sop_inlinesigned **out);
/* if the inlinesigned object uses the Cleartext Signing framework,
 * the armor parameter is ignored.
sop_inlinesigned_to_bytes (const sop_inlinesigned *inlinesigned,
                           bool armor, sop_buf **out);
sop_inlinesigned_free (sop_inlinesigned *inlinesigned);

/* sop inline-sign */
sop_op_sign_inline_execute (sop_op_sign *sign,
                            sop_inline_sign_as sign_as,
                            const uint8_t *msg,
                            size_t sz,
                            sop_inlinesigned **out);

/* sop inline-verify */
sop_op_verify_inline_execute (sop_op_verify *verify,
                              const sop_inlinesigned *msg,
                              sop_verifications **verifications_out,
                              sop_buf **msg_out);

/* sop inline-detach */
sop_inlinesigned_detach (const sop_inlinesigned *msg,
                         sop_sigs **sigs_out,
                         sop_buf **msg_out);

#endif // __SOP_H__

This proposed interface currently deals only with signing. Encryption and decryption will be added in a future revision.

A.1. Design Choices for Library API

The library is deliberately minimal, with data types and functionality corresponding to the SOP CLI. The interface itself should expose no dependencies beyond libc.

All datatypes are opaque structs. Library implementations MUST NOT expose library users to the memory layout of the underlying objects.

The library deals with data that is all in RAM, and produces data in RAM. For simplicity, it does not currently expose a streaming interface.

It should be fairly straightforward to implement the SOP CLI on top of such a library.

A.2. Library Use Patterns

There are two main kinds of data structures: operations (e.g., sop_op_sign and sop_op_verify) and datatypes (e.g., sop_keys and sop_certs).

Operation objects are one-shot objects. They are used in the following pattern:

  • create an operations object (sop_op_*_new)

  • adjust it to behave in certain ways (e.g., sop_op_sign_use_keys, sop_op_verify_not_before)

  • execute it (with some specific sop_op_*_execute function)

  • dispose of it (sop_op_*_free)

The library user MUST NOT execute the same operation object more than once. When a single operation object is executed more than once, it should fail with SOP_OPERATION_ALREADY_EXECUTED. FIXME: if a use case arises with a reasonable need to re-execute an already adjusted object, we could extend the API to allow the user to clone an object.

Datatype objects are reusable objects. For example, it is fine for a library user to pass the same sop_certs to multiple sop_op_* operation objects, as long as the sop_certs object is not freed before the execution of all the operation objects it has been passed to.

Datatype objects are also immutable. Any function which modifies a datatype object always creates a new copy of the object, with the specific change applied. This immutability avoids any ambguity about what should happen when a datatype object is adjusted after it was passed to an operation object but before it was executed.

A.3. libsopv C API Subset

A minimalist library subset that only does OpenPGP signature verification might be called libsopv. This library is useful wherever the use case is just OpenPGP signature verification.

Such a library MUST implement the following functions from the C API:

  • sop_ctx_new

  • sop_ctx_free

  • sop_set_log_function

  • sop_set_log_level

  • sop_version

  • sop_version_backend

  • sop_version_extended

  • sop_buf_size

  • sop_buf_data

  • sop_buf_free

  • sop_certs_from_bytes

  • sop_certs_free

  • sop_sigs_from_bytes

  • sop_sigs_free

  • sop_verifications_count

  • sop_verifications_get_time

  • sop_verifications_get_mode

  • sop_verifications_to_text

  • sop_verifications_free

  • sop_inlinesigned_from_bytes

  • sop_op_verify_new

  • sop_op_verify_not_before

  • sop_op_verify_not_after

  • sop_op_verify_add_signers

  • sop_op_verify_detached_execute

  • sop_op_verify_inline_execute

  • sop_op_verify_free

This minimal library interface should be sufficient to implement the sopv subset (see Section 3).

Appendix B. Acknowledgements

This work was inspired by Justus Winter's [OpenPGP-Interoperability-Test-Suite].

The following people contributed helpful feedback and considerations to this draft, but are not responsible for its problems:

Appendix C. Future Work

Appendix D. Document History

D.1. Substantive Changes between -09 and -10:

  • drop @HARDWARE: special designator in favor of the simple [I-D.dkg-openpgp-hardware-secrets] or other magic

  • drop hardware-specific C API function

  • define SemVer-versioned sopv subset of CLI

  • sop version: add --sopv option

  • define libsopv subset of C API

  • explicitly require BAD_DATA failure when KEYS are passed as CERTS

D.2. Substantive Changes between -08 and -09:

  • enable the use of hardware-backed secret key material via the @HARDWARE: special designator

  • C API: clarify design goals and usage patterns

  • C API: major overhaul and normalization:

    • allow passthrough "cookie" for logging

    • allow NULL return from sop_version_*

    • explicitly offer SOP_LOG_NEVER

    • use *_from_bytes and *_to_bytes instead of *_import and *_export

    • datatype objects are now immutable

    • operation objects are one-shot

    • always return sop_err, even at a slight cost to C caller ergonomics

D.3. Substantive Changes between -07 and -08:

  • revoke-key, change-key-password: add --no-armor option

  • generate-key: should fail on non-UTF-8 USERID

  • generate-key: acknowledge that implementations MAY reject USERIDs that seem bad

  • armor: drop --label option

  • encrypt: add --session-key-out option

  • ASCII-armored objects should not be concatenated

  • signature verification should only work for sigtypes 0x00 (binary) and 0x01 (canonical text)

  • sign: Constrain input when --micalg-out is present for alignment with [RFC3156]

  • propose simple C API for signing and verification

D.4. Substantive Changes between -06 and -07:

  • generate-key: add --signing-only option

  • new key management subcommand: change-key-password

  • new key management subcommand: revoke-key

D.5. Substantive Changes between -05 and -06:

  • version: add --sop-spec argument

  • encrypt: add --profile argument

D.6. Substantive Changes between -04 and -05:

  • decrypt: change --verify-out to --verifications-out

  • encrypt: add missing --with-key-password

  • add the concept of "profiles", use with generate-key

  • include table of known implementations

  • VERIFICATIONS can now indicate the type of the signature (mode:text or mode:binary)

D.7. Substantive Changes between -03 and -04:

  • Reinforce that PASSWORD and SESSIONKEY are indirect data types

  • encrypt: remove --as=mime option

  • Handle password-locked secret key material: add --with-key-password options to generate-key, sign, and decrypt.

  • Introduce INLINESIGNED message type (Section 6.5)

  • Rename detach-inband-signature-and-message to inline-detach, clarify its possible inputs

  • Add inline-verify

  • Add inline-sign

D.8. Substantive Changes between -02 and -03:

  • Added --micalg-out parameter to sign

  • Change from KEY to KEYS (permit multiple secret keys in each blob)

  • New error code: KEY_CANNOT_SIGN

  • version now has --backend and --extended options

D.9. Substantive Changes between -01 and -02:

  • Added mnemonics for return codes

  • decrypt should fail when asked to output to a pre-existing file

  • Removed superfluous --armor option

  • Much more specific about what armor --label=auto should do

  • armor and dearmor are now fully idempotent, but work only well-formed OpenPGP streams

  • Dropped armor --allow-nested

  • Specified what encrypt --as= means

  • New error code: KEY_IS_PROTECTED

  • Documented expectations around human-readable, human-transferable passwords

  • New subcommand: detach-inband-signature-and-message

  • More specific guidance about special designators like @FD: and @ENV:, including new error codes UNSUPPORTED_SPECIAL_PREFIX and AMBIGUOUS_INPUT

D.10. Substantive Changes between -00 and -01:

  • Changed generate subcommand to generate-key

  • Changed convert subcommand to extract-cert

  • Added "Input String Types" section as distinct from indirect I/O

  • Made implicit arguments potentially explicit (e.g., sop armor --label=auto)

  • Added --allow-nested to sop armor to make it idempotent by default

  • Added fingerprint of signing (sub)key to VERIFICATIONS output

  • Dropped --mode and --session-key arguments for sop encrypt (no plausible use, not needed for interop)

  • Added --with-session-key argument to sop decrypt to allow for session-key-based decryption

  • Added examples to each subcommand

  • More detailed error codes for sop encrypt

  • Move from CERT to CERTS (each CERTS argument might contain multiple certificates)

Author's Address

Daniel Kahn Gillmor
American Civil Liberties Union
125 Broad St.
New York, NY, 10004
United States of America