Files
pdfcraft/crates/sign
6116b0034c M9: name the Windows store certificates that can't sign (#179) (#761)
A store certificate PdfCraft can't use (no private key, a P-521 /
Brainpool / Ed25519 key, a key CNG can't open) was dropped from the
Sign dialog silently, so a user whose CA-issued identity shows in
Acrobat but not here had nothing to go on. `windows::list` now returns
those under `unusable` with the subject, fingerprint and a reason that
names the Windows error code; the Sign dialog shows them greyed and
unselectable with the reason, and `sign_windows_ids` returns them.
A key that needs a prompt to open (NTE_SILENT_CONTEXT, NTE_UI_REQUIRED
while listing) is listed and prompts at signing instead of being
skipped. Certificates without a private key stay out of the dialog but
are reported by the tool.

Tests: the explained-error table, the store listing's invariants, a
key-less certificate in the ignored store test, the automation output,
and a kittest dialog test for a greyed entry. Verified by hand that a
.p12 imported into the CNG and legacy Microsoft providers lists, and
that a P-521 certificate is explained.

Co-authored-by: Claude Fable 5.1 <noreply@anthropic.com>
Co-authored-by: Brandon Thomas <echelon@gmail.com>
2026-10-10 16:25:24 -04:00
..

pdfcraft-sign

Layer L4: digital signatures (execution plan M9; ISO 32000-2 §12.8; PAdES, ETSI EN 319 142).

let id = pkcs12::open(&std::fs::read("me.p12")?, "password")?;          // a digital ID
let signed = sign(&doc, &id, &SignOptions { page: 0, rect: Some(r), date, ..Default::default() })?;
for s in signatures(&doc, &bytes, &trust) {                                // list + validate
    println!("{}: {} — {:?}", s.field, s.summary(), s.details);
}
  • Formats, on RustCrypto primitives: a small DER reader and writer (der), X.509 certificates (x509), CMS SignedData (cms), and PKCS #12 digital ID files (pkcs12): PBES2 (PBKDF2 + AES/3DES), the legacy SHA-1 3DES/RC2 schemes, and MAC checks. Writing uses OpenSSL 3's defaults (AES-256-CBC, HMAC-SHA-256).
  • Keys: RSA, ECDSA P-256 and P-384. Verification uses RustCrypto everywhere. RSA private-key operations (signing, key generation) use aws-lc-rs on native targets and are refused in the browser (ADR-0009: the rsa crate's Marvin advisory, RUSTSEC-2023-0071, has no fix, so rsa is only used to verify). ECDSA signs with deterministic nonces (RFC 6979).
  • Signing: PAdES B-B (ETSI.CAdES.detached, signing-certificate-v2, SHA-256/384, no SHA-1). An existing unsigned field or a new one (visible with Acrobat's name-and-details appearance, or invisible); certification with DocMDP P=1/2/3. The document is written incrementally with a zero-filled /Contents and fixed-width /ByteRange, which are then patched in place. Encrypted documents are refused for now.
  • Timestamps (PAdES B-T): the timestamp module builds and parses RFC 3161 requests, responses and TSTInfo tokens (size-capped, imprint- and signature-checked). sign_with_timestamp attaches the TSA's token as an unsigned attribute over the signature value; the transport is the caller's (TimestampAuthority — this crate never opens a socket). Validation verifies embedded tokens; when the TSA chains to the trust store it reports the trusted time in SignatureInfo::timestamp_time, which then anchors certificate-validity and revocation checks. An untrusted TSA's time is reported as an unverified timestamp and never used as the validation time (the signer's claimed time is). timestamp::respond is the TSA-side signer behind the deterministic test authority.
  • Document timestamps and LTV: timestamp_document appends a standalone RFC 3161 document timestamp (/ETSI.RFC3161) covering the whole file; validation discovers and verifies these dictionaries (imprint over the signed bytes, token signature, TSA cert validity). dss::embed merges revocation evidence into the catalog's /DSS with /VRI entries keyed per signature (uppercase-hex SHA-1 of /Contents), deduplicating byte-identical blobs — sign → DSS → timestamp makes a B-LTA file, and the change classifier treats the store as a permitted change: only objects reached through /Certs, /CRLs, /OCSPs and /VRI with the shape of their role, and new or only grown since the signature, count (a /DSS entry naming a page's contents, or a /Type /DSS label, does not). revocation parses and verifies RFC 5280 CRLs and RFC 6960 OCSP responses (responder identity, OCSP-signing EKU for delegated responders, CertID hash matching, validity windows); validation checks embedded evidence against the signer's chain and a verified revocation invalidates the signature.

Not yet: revocation fetching (AIA/CRLDP extraction and a fetcher), timestamp-server configuration, FieldMDP locks, certificate security, direct PKCS #11 access to tokens. macOS Keychain and Windows Current User Personal (My) store identities sign through ExternalKey without exporting private keys. Windows CNG supports RSA PKCS #1 v1.5 and ECDSA P-256/P-384; the store integration is tested with software-backed keys. A smart card or token whose driver registers a CNG key storage provider is such an identity too: the key is opened for signing without the silent flag, so the provider shows its own PIN dialog (checked by hand with a SafeNet token; CI has no hardware). A store identity signs with the issuers Windows chains its certificate to, without the root. Store certificates that can't sign (no private key, another key type, a key CNG can't open) are returned by windows::list as unusable with the reason and the Windows error code, shown greyed in the Sign dialog and by sign_windows_ids, instead of being left out silently; a key that needs a prompt to open is listed and asks at signing (issue #179).

  • Validation: /ByteRange and the CMS are read from the file's own bytes; the digest, the signature value and the signer's chain (against a TrustStore) are checked. Later revisions are diffed against the signed one, and the changes are classified (signing, form fill, comments, metadata, page content, document structure) under the DocMDP permissions. The verdict follows Acrobat: valid, unknown (intact but the identity isn't trusted) or invalid.
  • Chains are checked, not just linked. x509::build_chain only takes an issuer whose key verifies the certificate below it and that may issue: basicConstraints CA:TRUE (an old v1 self-signed root without constraints counts), keyCertSign when it has a key usage, a pathLenConstraint that allows the CAs below it, and, given the signing time, validity then. Certificates embedded in a document are in the pool too, so an ordinary subscriber certificate can never vouch for another one; when an issuer is refused, the signature's details say why.
  • The signer's certificate must allow signing documents (Certificate::signing_problem): a key usage needs digitalSignature or nonRepudiation, an extended key usage needs a document-signing purpose (any, emailProtection, codeSigning, RFC 9336 documentSigning, Adobe Authentic Documents, Microsoft document signing), and no critical extension may be one PdfCraft doesn't process. Otherwise the verdict is unknown, never valid, and the details say why.
  • BER as well as DER. The CMS is read with der::Tlv::parse_ber, as Windows CryptoAPI, Adobe PPKMS, DocuSign, Documenso and openssl cms -stream write it: indefinite lengths and an OCTET STRING split into segments. Only the structure is read that way; certificates and signed attributes are still verified over their own exact bytes (signed attributes written with an indefinite length are re-encoded as DER first, as RFC 5652 §5.4 has them signed). Nesting is bounded, and the details say that the signature was BER. High tag numbers are not read.
  • Later changes are classified narrowly. Only the catalog's own /Metadata stream is the document's XMP, and only objects reached through the /DSS keys above are the security store. A /Type /Metadata or /Type /DSS label on any other dictionary or stream (a page's Form XObject, say) makes nothing permitted, at every DocMDP level.
  • Strict in what it checks, tolerant where signers differ. RSA PKCS #1 signatures are checked against the one encoding the digest should have, built here and compared byte for byte; the DigestInfo may omit its NULL parameter, as older signers write it (RFC 8017 App. B.1), but a signature over the bare digest, which doesn't say which hash it uses, is refused. A signature value must be below the modulus (RFC 8017 §5.2.2). RSA-PSS uses the salt length it declares. ECDSA is read as DER, non-minimal DER or raw r ‖ s. adbe.x509.rsa_sha1 is validated. What the check tolerated is listed in the signature's details: a DigestInfo without its NULL, an RSA value that isn't modulus-length, ECDSA that isn't canonical DER, a SignerInfo whose digest algorithm differs from the one the signature algorithm names. What PdfCraft can't check (an unknown algorithm or curve) is unknown, never invalid.
  • Weak algorithms still validate, and say so. SHA-1 and RIPEMD-160 signatures are common in documents signed years ago, so they validate (new signatures never use SHA-1), but the signature's details say that the algorithm is weak and shouldn't be relied on.
  • Validation algorithms: digests SHA-1, SHA-224/256/384/512, SHA-512/224, SHA-512/256, SHA3-224/256/384/512 and RIPEMD-160. RSA PKCS #1 v1.5 and RSASSA-PSS (the hash, MGF1 hash and salt length the signature declares), ECDSA on P-256, P-384, P-521, brainpoolP256r1, P384r1 and P512r1 (also BSI "plain" ECDSA), and Ed25519 (RFC 8419, over the signed attributes). Signing: RSA, P-256, P-384 with SHA-256/384/512. The RSA padding checks and brainpoolP512r1 are written here (rsa_pad, ec512) on crypto-bigint, because the typed APIs of the rsa crate and RustCrypto don't cover them.

Oracles: poppler's pdfsig reports our signatures valid; OpenSSL reads our .p12 files and verifies our CMS; tests/data/openssl-signed.pdf is a signature OpenSSL made, which we validate.