Files
pdfcraft/crates/cos/tests/encryption.rs
T
Brandon ThomasandClaude Opus 5.5 d3db99818f Rename PrintCraft to PdfCraft (#174)
The app, crates, binaries, bundle id, packaging, icons, screenshots and docs are now
PdfCraft / pdfcraft (repo storytold/pdfcraft). On first launch the desktop app moves the
PrintCraft settings and crash-recovery folders to the new name, and both apps read settings
saved under the old storage key, so upgrades keep recent files, preferences and unsaved work.
The signing test fixtures keep their PrintCraft subject names (they are binary).

Co-authored-by: Claude Opus 5.5 <noreply@anthropic.com>
2026-10-07 16:03:57 -04:00

198 lines
10 KiB
Rust
Raw Blame History

This file contains ambiguous Unicode characters
This file contains Unicode characters that might be confused with other characters. If you think that this is intentional, you can safely ignore this warning. Use the Escape button to reveal them.
//! Encryption end to end: protect a document with every algorithm, save it, and read it back
//! with our reader and with an independent one (hayro-syntax's decryption). Also editing
//! encrypted documents incrementally, changing and removing passwords, and permissions.
use std::sync::Arc;
use pdfcraft_cos::{Algorithm, Auth, CosError, Document, NewEncryption, ObjRef, Object, PdfString, SaveOptions, write_full, write_incremental};
const SECRET: &str = "BT /F1 18 Tf 20 100 Td (Secret page) Tj ET";
fn fixture() -> Vec<u8> {
let objs = [
"<< /Type /Catalog /Pages 2 0 R /Metadata 6 0 R >>".to_string(),
"<< /Type /Pages /Kids [3 0 R] /Count 1 /MediaBox [0 0 300 200] >>".to_string(),
"<< /Type /Page /Parent 2 0 R /Contents 4 0 R /Resources << /Font << /F1 5 0 R >> >> >>".to_string(),
format!("<< /Length {} >>\nstream\n{SECRET}\nendstream", SECRET.len()),
"<< /Type /Font /Subtype /Type1 /BaseFont /Helvetica >>".to_string(),
"<< /Type /Metadata /Subtype /XML /Length 22 >>\nstream\n<x:xmpmeta>meta</x:xmpmeta>\nendstream".replace("22", "26"),
"<< /Title (Quarterly numbers) >>".to_string(),
];
let mut out = b"%PDF-1.7\n".to_vec();
let mut offsets = Vec::new();
for (i, o) in objs.iter().enumerate() {
offsets.push(out.len());
out.extend_from_slice(format!("{} 0 obj\n{o}\nendobj\n", i + 1).as_bytes());
}
let xref = out.len();
out.extend_from_slice(format!("xref\n0 {}\n0000000000 65535 f \n", objs.len() + 1).as_bytes());
for o in offsets {
out.extend_from_slice(format!("{o:010} 00000 n \n").as_bytes());
}
out.extend_from_slice(format!("trailer\n<< /Size {} /Root 1 0 R /Info 7 0 R >>\nstartxref\n{xref}\n%%EOF\n", objs.len() + 1).as_bytes());
out
}
fn protect(alg: Algorithm, user: &str, owner: &str, permissions: i32) -> Vec<u8> {
let mut doc = Document::open(Arc::new(fixture())).unwrap();
doc.set_encryption(&NewEncryption {
algorithm: alg,
user_password: user,
owner_password: owner,
permissions,
encrypt_metadata: true,
seed: [9; 32],
})
.unwrap();
write_full(&doc, &SaveOptions::default()).unwrap()
}
fn content(doc: &Document) -> String {
let catalog = doc.get(doc.root().unwrap()).as_dict().cloned().unwrap();
let pages = doc.get(catalog.reference(b"Pages").unwrap()).as_dict().cloned().unwrap();
let page = doc.resolve(&pages.get(b"Kids").unwrap().as_array().unwrap()[0]).as_dict().cloned().unwrap();
match doc.resolve(page.get(b"Contents").unwrap()).as_ref() {
Object::Stream(s) => String::from_utf8_lossy(&s.decoded().unwrap()).trim().to_string(),
_ => panic!("no content stream"),
}
}
fn title(doc: &Document) -> Option<String> {
let info = doc.resolve(doc.trailer().get(b"Info")?);
info.as_dict()?.get(b"Title").and_then(|t| doc.resolve(t).as_string().map(|s| s.to_text()))
}
const ALL: [Algorithm; 4] = [Algorithm::Rc4_40, Algorithm::Rc4_128, Algorithm::Aes128, Algorithm::Aes256];
#[test]
fn every_algorithm_round_trips_and_hides_the_content() {
for alg in ALL {
let bytes = protect(alg, "user", "owner", -1);
let raw = String::from_utf8_lossy(&bytes);
assert!(!raw.contains("Secret page") && !raw.contains("Quarterly"), "{alg:?}: plaintext leaked");
let bytes = Arc::new(bytes);
assert!(matches!(Document::open(bytes.clone()), Err(CosError::NeedsPassword)), "{alg:?}");
assert!(matches!(Document::open_with_password(bytes.clone(), Some("guess")), Err(CosError::WrongPassword)), "{alg:?}");
let user = Document::open_with_password(bytes.clone(), Some("user")).unwrap();
assert_eq!(user.security().unwrap().auth(), Auth::User);
assert_eq!(content(&user), SECRET, "{alg:?}");
assert_eq!(title(&user).as_deref(), Some("Quarterly numbers"), "{alg:?}");
let owner = Document::open_with_password(bytes.clone(), Some("owner")).unwrap();
assert_eq!(owner.security().unwrap().auth(), Auth::Owner);
// Independent check: hayro decrypts our output. hayro-syntax 0.7 has no owner-password
// authentication for R2–R4 (Algorithm 7), so for those qpdf is the owner-password oracle
// (`qpdf_agrees`); hayro checks every user password and R6 owner passwords.
for pw in if alg == Algorithm::Aes256 { &["user", "owner"][..] } else { &["user"][..] } {
let hay = hayro_syntax::Pdf::new_with_password(bytes.as_ref().clone(), pw).unwrap_or_else(|e| panic!("{alg:?}/{pw}: {e:?}"));
let page = hay.pages().first().unwrap().page_stream().map(|s| String::from_utf8_lossy(s).trim().to_string());
assert_eq!(page.as_deref(), Some(SECRET), "{alg:?}/{pw}");
}
assert!(hayro_syntax::Pdf::new(bytes.as_ref().clone()).is_err(), "{alg:?}: hayro must not open it without a password");
}
}
#[test]
fn empty_user_password_opens_but_reports_restrictions() {
let bytes = Arc::new(protect(Algorithm::Aes256, "", "owner", 0b0100)); // print only
let doc = Document::open(bytes.clone()).unwrap();
let p = doc.permissions().unwrap();
assert!(p.print() && !p.modify() && !p.copy() && !p.assemble());
let owner = Document::open_with_password(bytes, Some("owner")).unwrap();
assert!(owner.permissions().unwrap().modify(), "the owner may do everything");
assert!(Document::open(Arc::new(fixture())).unwrap().permissions().is_none(), "unencrypted: no restrictions");
}
#[test]
fn incremental_edits_of_encrypted_documents_stay_encrypted() {
for alg in ALL {
let original = protect(alg, "user", "owner", -1);
let mut doc = Document::open_with_password(Arc::new(original.clone()), Some("user")).unwrap();
let info = doc.trailer().reference(b"Info").unwrap();
doc.update_dict(info, |d| d.set(b"Title".to_vec(), Object::String(PdfString::text("Revised figures")))).unwrap();
let saved = write_incremental(&doc, &SaveOptions::default()).unwrap();
assert_eq!(&saved[..original.len()], &original[..], "{alg:?}: incremental");
assert!(!String::from_utf8_lossy(&saved).contains("Revised"), "{alg:?}: new string encrypted");
let again = Document::open_with_password(Arc::new(saved.clone()), Some("user")).unwrap();
assert_eq!(title(&again).as_deref(), Some("Revised figures"), "{alg:?}");
assert_eq!(content(&again), SECRET);
assert!(hayro_syntax::Pdf::new_with_password(saved, "user").is_ok(), "{alg:?}");
}
}
#[test]
fn changing_and_removing_passwords() {
let bytes = protect(Algorithm::Rc4_128, "old", "old-owner", -1);
// Change: decrypt with the old handler, encrypt with the new one.
let mut doc = Document::open_with_password(Arc::new(bytes), Some("old-owner")).unwrap();
doc.set_encryption(&NewEncryption {
algorithm: Algorithm::Aes256,
user_password: "new",
owner_password: "new-owner",
permissions: -1,
encrypt_metadata: true,
seed: [3; 32],
})
.unwrap();
let changed = Arc::new(write_incremental(&doc, &SaveOptions::default()).unwrap()); // falls back to a full save
assert!(Document::open_with_password(changed.clone(), Some("old")).is_err());
let doc = Document::open_with_password(changed.clone(), Some("new")).unwrap();
assert_eq!(content(&doc), SECRET);
assert_eq!(doc.security().unwrap().dict().r, 6);
// Remove.
let mut doc = Document::open_with_password(changed, Some("new-owner")).unwrap();
doc.remove_encryption();
let plain = write_incremental(&doc, &SaveOptions::default()).unwrap();
assert!(String::from_utf8_lossy(&plain).contains("Secret page"));
let doc = Document::open(Arc::new(plain.clone())).unwrap();
assert!(doc.security().is_none() && !doc.trailer().contains(b"Encrypt"));
assert_eq!(title(&doc).as_deref(), Some("Quarterly numbers"));
assert!(hayro_syntax::Pdf::new(plain).is_ok());
}
#[test]
fn unencrypted_metadata_is_left_readable() {
let mut doc = Document::open(Arc::new(fixture())).unwrap();
doc.set_encryption(&NewEncryption {
algorithm: Algorithm::Aes256,
user_password: "",
owner_password: "o",
permissions: -1,
encrypt_metadata: false,
seed: [5; 32],
})
.unwrap();
let bytes = write_full(&doc, &SaveOptions::default()).unwrap();
assert!(String::from_utf8_lossy(&bytes).contains("<x:xmpmeta>meta</x:xmpmeta>"), "search engines can read XMP");
assert!(!String::from_utf8_lossy(&bytes).contains("Secret page"));
let doc = Document::open(Arc::new(bytes)).unwrap();
let catalog = doc.get(doc.root().unwrap()).as_dict().cloned().unwrap();
let meta = doc.get(catalog.reference(b"Metadata").unwrap());
let Object::Stream(s) = meta.as_ref() else { panic!() };
assert_eq!(s.decoded().unwrap(), b"<x:xmpmeta>meta</x:xmpmeta>");
let _ = ObjRef::new(1, 0);
}
/// Second independent oracle when qpdf is installed: it must accept both passwords, identify
/// the owner password, and find no structural errors.
#[test]
fn qpdf_agrees() {
if std::process::Command::new("qpdf").arg("--version").output().is_err() {
eprintln!("qpdf not installed; skipping");
return;
}
let dir = std::env::temp_dir().join(format!("pdfcraft-enc-{}", std::process::id()));
std::fs::create_dir_all(&dir).unwrap();
for alg in ALL {
let path = dir.join(format!("{alg:?}.pdf"));
std::fs::write(&path, protect(alg, "user", "owner", -1)).unwrap();
for (pw, expect) in [("user", "user password"), ("owner", "owner password")] {
let out = std::process::Command::new("qpdf").arg(format!("--password={pw}")).arg("--show-encryption").arg(&path).output().unwrap();
let text = String::from_utf8_lossy(&out.stdout);
assert!(text.contains(&format!("Supplied password is {expect}")), "{alg:?}/{pw}: {text}");
let check = std::process::Command::new("qpdf").arg(format!("--password={pw}")).arg("--check").arg(&path).output().unwrap();
assert!(check.status.success(), "{alg:?}/{pw}: {}", String::from_utf8_lossy(&check.stdout));
}
}
let _ = std::fs::remove_dir_all(dir);
}