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rpdfium_parser/
security.rs

1// Derived from PDFium's core/fpdfapi/parser/cpdf_security_handler.cpp
2// Original: Copyright 2014 The PDFium Authors
3// Licensed under BSD-3-Clause / Apache-2.0
4// See pdfium-upstream/LICENSE for the original license.
5
6//! PDF Standard Security Handler (R2–R6).
7//!
8//! Implements password verification and object/stream decryption
9//! per the PDF specification's Standard Security Handler.
10
11use std::collections::HashMap;
12
13use rpdfium_core::{Name, PdfSource};
14
15use crate::crypto::{self, CryptoError};
16use crate::object::{Object, ObjectId};
17use crate::store::ObjectStore;
18
19/// Padding string used in password computation (Table 3.18 in PDF spec).
20const PASSWORD_PADDING: [u8; 32] = [
21    0x28, 0xBF, 0x4E, 0x5E, 0x4E, 0x75, 0x8A, 0x41, 0x64, 0x00, 0x4E, 0x56, 0xFF, 0xFA, 0x01, 0x08,
22    0x2E, 0x2E, 0x00, 0xB6, 0xD0, 0x68, 0x3E, 0x80, 0x2F, 0x0C, 0xA9, 0xFE, 0x64, 0x53, 0x69, 0x7A,
23];
24
25/// Errors from the security handler.
26#[derive(Debug, thiserror::Error)]
27pub enum SecurityError {
28    /// The supplied password does not match owner or user password.
29    #[error("invalid password")]
30    InvalidPassword,
31    /// The encryption version/revision is not supported.
32    #[error("unsupported encryption version: V={0}, R={1}")]
33    UnsupportedVersion(u32, u32),
34    /// A required key is missing from the encryption dictionary.
35    #[error("missing encryption dictionary key: {0}")]
36    MissingKey(String),
37    /// An underlying cryptographic error.
38    #[error("crypto error: {0}")]
39    Crypto(#[from] CryptoError),
40}
41
42/// The method used by a crypt filter.
43#[derive(Debug, Clone, Copy, PartialEq, Eq)]
44pub enum CryptFilterMethod {
45    /// No encryption.
46    None,
47    /// RC4 encryption (V2).
48    V2,
49    /// AES-128 encryption (AESV2).
50    Aesv2,
51    /// AES-256 encryption (AESV3).
52    Aesv3,
53}
54
55/// Typed wrapper for the PDF permission bits stored in the `/P` field of the
56/// encrypt dictionary (PDF 1.7 spec, Table 3.20).
57///
58/// The raw value is a signed 32-bit integer where the upper bits are always 1
59/// per the spec; only bits 3, 5, 8, and 9 carry meaningful permission flags.
60#[derive(Debug, Clone, Copy, PartialEq, Eq)]
61pub struct Permissions(i32);
62
63impl Permissions {
64    /// Wrap a raw `/P` integer value.
65    pub fn from_bits(bits: i32) -> Self {
66        Self(bits)
67    }
68
69    /// Return the raw integer value.
70    pub fn bits(self) -> i32 {
71        self.0
72    }
73
74    /// Bit 4: Allow modifying document content.
75    pub fn modify_content(self) -> bool {
76        self.0 & (1 << 3) != 0
77    }
78
79    /// Bit 6: Allow adding, modifying, or deleting annotations.
80    pub fn modify_annotation(self) -> bool {
81        self.0 & (1 << 5) != 0
82    }
83
84    /// Bit 9: Allow filling in form fields and signing.
85    pub fn fill_form(self) -> bool {
86        self.0 & (1 << 8) != 0
87    }
88
89    /// Bit 10: Allow extracting text and graphics for accessibility.
90    pub fn extract_for_accessibility(self) -> bool {
91        self.0 & (1 << 9) != 0
92    }
93}
94
95/// PDF Standard Security Handler — holds the derived encryption key
96/// and methods for decrypting strings and streams.
97pub struct SecurityHandler {
98    revision: u32,
99    key_length_bytes: usize,
100    encryption_key: Vec<u8>,
101    permissions: Permissions,
102    encrypt_metadata: bool,
103    stream_cf: CryptFilterMethod,
104    string_cf: CryptFilterMethod,
105    /// The /O value (owner hash) from the encrypt dictionary.
106    o_value: Vec<u8>,
107    /// The /U value (user hash) from the encrypt dictionary.
108    u_value: Vec<u8>,
109}
110
111impl SecurityHandler {
112    /// Build a `SecurityHandler` from the `/Encrypt` dictionary, verifying the
113    /// password against the stored owner/user hashes.
114    ///
115    /// `encrypt_dict` is the resolved encryption dictionary.
116    /// `file_id` is the first element of the trailer `/ID` array.
117    pub fn from_encrypt_dict<S: PdfSource>(
118        encrypt_dict: &HashMap<Name, Object>,
119        store: &ObjectStore<S>,
120        password: &str,
121        file_id: &[u8],
122    ) -> Result<Self, SecurityError> {
123        // Parse required fields
124        let v = get_int(encrypt_dict, store, &Name::v())? as u32;
125        let r = get_int(encrypt_dict, store, &Name::r())? as u32;
126        let p = get_int(encrypt_dict, store, &Name::p())?;
127
128        let o_bytes = get_string_bytes(encrypt_dict, store, &Name::o())?;
129        let u_bytes = get_string_bytes(encrypt_dict, store, &Name::u())?;
130
131        // Key length: /Length in bits, default 40
132        let key_length_bits =
133            get_optional_int(encrypt_dict, store, &Name::length()).unwrap_or(40) as usize;
134        let key_length_bytes = key_length_bits / 8;
135
136        // Validate key length to prevent panics in key derivation.
137        // R2-R4: 40-128 bits (5-16 bytes); R5-R6 always use 256-bit (32 bytes).
138        if r <= 4 && !(5..=16).contains(&key_length_bytes) {
139            return Err(SecurityError::UnsupportedVersion(v, r));
140        }
141
142        // EncryptMetadata: default true
143        let encrypt_metadata =
144            get_optional_bool(encrypt_dict, store, &Name::encrypt_metadata()).unwrap_or(true);
145
146        // Determine crypt filter methods for streams and strings
147        let (stream_cf, string_cf) = if v >= 4 {
148            let stm = parse_single_crypt_filter(encrypt_dict, store, &Name::stm_f());
149            let str_ = parse_single_crypt_filter(encrypt_dict, store, &Name::str_f());
150            (stm, str_)
151        } else if v == 1 || v == 2 || v == 3 {
152            (CryptFilterMethod::V2, CryptFilterMethod::V2)
153        } else {
154            (CryptFilterMethod::None, CryptFilterMethod::None)
155        };
156
157        match (v, r) {
158            (1, 2) | (2, 3) | (3, 3) | (4, 4) => {
159                // R2-R4: MD5-based key derivation
160                let pwd_bytes = encode_password_latin1(password);
161                let key = derive_key_r2_r4(
162                    &pwd_bytes,
163                    &o_bytes,
164                    p as i32,
165                    file_id,
166                    r,
167                    key_length_bytes,
168                    encrypt_metadata,
169                );
170
171                // Try user password first
172                if verify_user_password_r2_r4(&key, &u_bytes, r, file_id) {
173                    return Ok(Self {
174                        revision: r,
175                        key_length_bytes,
176                        encryption_key: key,
177                        permissions: Permissions::from_bits(p as i32),
178                        encrypt_metadata,
179                        stream_cf,
180                        string_cf,
181                        o_value: o_bytes.clone(),
182                        u_value: u_bytes.clone(),
183                    });
184                }
185
186                // Try as owner password: recover user password from O value
187                let user_password =
188                    recover_user_password_from_owner(&pwd_bytes, &o_bytes, r, key_length_bytes);
189                let key = derive_key_r2_r4(
190                    &user_password,
191                    &o_bytes,
192                    p as i32,
193                    file_id,
194                    r,
195                    key_length_bytes,
196                    encrypt_metadata,
197                );
198
199                if verify_user_password_r2_r4(&key, &u_bytes, r, file_id) {
200                    Ok(Self {
201                        revision: r,
202                        key_length_bytes,
203                        encryption_key: key,
204                        permissions: Permissions::from_bits(p as i32),
205                        encrypt_metadata,
206                        stream_cf,
207                        string_cf,
208                        o_value: o_bytes,
209                        u_value: u_bytes,
210                    })
211                } else {
212                    Err(SecurityError::InvalidPassword)
213                }
214            }
215            (5, 5) | (5, 6) => {
216                // R5/R6: SHA-256 based (ISO 32000-2)
217                let oe_bytes = get_string_bytes(encrypt_dict, store, &Name::oe())?;
218                let ue_bytes = get_string_bytes(encrypt_dict, store, &Name::ue())?;
219
220                let key = if r == 5 {
221                    derive_key_r5(password, &u_bytes, &ue_bytes, &o_bytes, &oe_bytes)?
222                } else {
223                    derive_key_r6(password, &u_bytes, &ue_bytes, &o_bytes, &oe_bytes)?
224                };
225
226                match key {
227                    Some(k) => {
228                        // P2-33: Validate /Perms entry (R5/R6).
229                        //
230                        // Upstream deviation — /Perms is required:
231                        //
232                        // Upstream PDFium (`AES256_CheckPassword`) returns `false`
233                        // when `/Perms` is missing or empty. We match that behavior
234                        // by requiring the entry to be present and at least 16 bytes.
235                        // The previous implementation silently skipped validation
236                        // when `/Perms` was absent or malformed, which could allow
237                        // an attacker to strip `/Perms` and tamper with the `/P`
238                        // permission bits without detection.
239                        let perms_bytes = get_string_bytes(encrypt_dict, store, &Name::perms())?;
240                        if perms_bytes.len() < 16 {
241                            return Err(SecurityError::MissingKey(
242                                "Perms (too short, need ≥16 bytes)".into(),
243                            ));
244                        }
245                        let decrypted = crypto::aes256_ecb_decrypt_block(&k, &perms_bytes[..16])?;
246                        // Verify bytes 9-11 = "adb" (PDF spec Algorithm 2.A step 2).
247                        // Byte 8 is the EncryptMetadata flag ('T'/'F'), checked
248                        // separately. Upstream PDFium checks only bytes 9-11.
249                        if &decrypted[9..12] != b"adb" {
250                            return Err(SecurityError::InvalidPassword);
251                        }
252                        // Verify bytes 0-3 match /P as LE i32
253                        let perms_p = i32::from_le_bytes([
254                            decrypted[0],
255                            decrypted[1],
256                            decrypted[2],
257                            decrypted[3],
258                        ]);
259                        if perms_p != p as i32 {
260                            return Err(SecurityError::InvalidPassword);
261                        }
262
263                        Ok(Self {
264                            revision: r,
265                            key_length_bytes: 32,
266                            encryption_key: k,
267                            permissions: Permissions::from_bits(p as i32),
268                            encrypt_metadata,
269                            stream_cf: CryptFilterMethod::Aesv3,
270                            string_cf: CryptFilterMethod::Aesv3,
271                            o_value: o_bytes,
272                            u_value: u_bytes,
273                        })
274                    }
275                    None => Err(SecurityError::InvalidPassword),
276                }
277            }
278            _ => Err(SecurityError::UnsupportedVersion(v, r)),
279        }
280    }
281
282    /// Return the document access permissions stored in the `/P` entry.
283    pub fn permissions(&self) -> Permissions {
284        self.permissions
285    }
286
287    /// Decrypt a string value belonging to the given object.
288    pub fn decrypt_string(&self, data: &[u8], obj_id: ObjectId) -> Vec<u8> {
289        if self.string_cf == CryptFilterMethod::None {
290            return data.to_vec();
291        }
292
293        if self.revision >= 5 {
294            // R5/R6: AES-256 with the file encryption key directly
295            crypto::aes256_cbc_decrypt(&self.encryption_key, data).unwrap_or_else(|_| data.to_vec())
296        } else {
297            let object_key = self.compute_object_key(obj_id, self.string_cf);
298            match self.string_cf {
299                CryptFilterMethod::V2 => crypto::rc4_crypt(&object_key, data),
300                CryptFilterMethod::Aesv2 => {
301                    crypto::aes128_cbc_decrypt(&object_key, data).unwrap_or_else(|_| data.to_vec())
302                }
303                CryptFilterMethod::Aesv3 => crypto::aes256_cbc_decrypt(&self.encryption_key, data)
304                    .unwrap_or_else(|_| data.to_vec()),
305                CryptFilterMethod::None => data.to_vec(),
306            }
307        }
308    }
309
310    /// Decrypt stream data belonging to the given object.
311    pub fn decrypt_stream(&self, data: &[u8], obj_id: ObjectId) -> Vec<u8> {
312        if self.stream_cf == CryptFilterMethod::None {
313            return data.to_vec();
314        }
315
316        if self.revision >= 5 {
317            crypto::aes256_cbc_decrypt(&self.encryption_key, data).unwrap_or_else(|_| data.to_vec())
318        } else {
319            let object_key = self.compute_object_key(obj_id, self.stream_cf);
320            match self.stream_cf {
321                CryptFilterMethod::V2 => crypto::rc4_crypt(&object_key, data),
322                CryptFilterMethod::Aesv2 => {
323                    crypto::aes128_cbc_decrypt(&object_key, data).unwrap_or_else(|_| data.to_vec())
324                }
325                CryptFilterMethod::Aesv3 => crypto::aes256_cbc_decrypt(&self.encryption_key, data)
326                    .unwrap_or_else(|_| data.to_vec()),
327                CryptFilterMethod::None => data.to_vec(),
328            }
329        }
330    }
331
332    /// Whether metadata streams should be encrypted.
333    pub fn encrypt_metadata(&self) -> bool {
334        self.encrypt_metadata
335    }
336
337    /// The encryption revision number.
338    pub fn revision(&self) -> u32 {
339        self.revision
340    }
341
342    /// The crypt filter method in use (returns stream filter for backwards compat).
343    pub fn crypt_filter_method(&self) -> CryptFilterMethod {
344        self.stream_cf
345    }
346
347    /// The encryption key length in bytes.
348    pub fn key_length_bytes(&self) -> usize {
349        self.key_length_bytes
350    }
351
352    /// The raw encryption key.
353    pub fn encryption_key(&self) -> &[u8] {
354        &self.encryption_key
355    }
356
357    /// The stream crypt filter method.
358    pub fn stream_crypt_filter(&self) -> CryptFilterMethod {
359        self.stream_cf
360    }
361
362    /// The string crypt filter method.
363    pub fn string_crypt_filter(&self) -> CryptFilterMethod {
364        self.string_cf
365    }
366
367    /// The /O value (owner hash) from the encrypt dictionary.
368    pub fn o_value(&self) -> &[u8] {
369        &self.o_value
370    }
371
372    /// The /U value (user hash) from the encrypt dictionary.
373    pub fn u_value(&self) -> &[u8] {
374        &self.u_value
375    }
376
377    /// The encryption version number (V value).
378    ///
379    /// Derived from the revision: R2→V1, R3/R4→V2..V4, R5/R6→V5.
380    pub fn version(&self) -> u32 {
381        match self.revision {
382            2 => 1,
383            3 | 4 => {
384                if self.stream_cf == CryptFilterMethod::V2
385                    && self.string_cf == CryptFilterMethod::V2
386                {
387                    if self.key_length_bytes == 5 { 1 } else { 2 }
388                } else {
389                    4
390                }
391            }
392            5 | 6 => 5,
393            _ => 0,
394        }
395    }
396
397    /// Encrypt a string value belonging to the given object.
398    ///
399    /// RC4 is symmetric (encrypt = decrypt). For AES, a zero IV is used
400    /// and prepended to the ciphertext (matching PDF convention where the
401    /// first 16 bytes of the encrypted data are the IV).
402    pub fn encrypt_string(&self, data: &[u8], obj_id: ObjectId) -> Vec<u8> {
403        if self.string_cf == CryptFilterMethod::None {
404            return data.to_vec();
405        }
406        self.encrypt_with_method(data, obj_id, self.string_cf)
407    }
408
409    /// Encrypt stream data belonging to the given object.
410    pub fn encrypt_stream(&self, data: &[u8], obj_id: ObjectId) -> Vec<u8> {
411        if self.stream_cf == CryptFilterMethod::None {
412            return data.to_vec();
413        }
414        self.encrypt_with_method(data, obj_id, self.stream_cf)
415    }
416
417    /// Encrypt data with the specified crypt filter method.
418    ///
419    /// # Panics
420    ///
421    /// Panics if AES encryption fails due to an invalid key length.
422    /// Key sizes are validated in [`SecurityHandler::from_encrypt_dict`], so
423    /// this should never happen in normal operation.
424    ///
425    /// # Upstream deviation — error handling
426    ///
427    /// Upstream PDFium (`CPDF_CryptoHandler::EncryptContent`) does not handle
428    /// encryption failure at this level — the C++ code assumes valid key sizes
429    /// and cannot return an error. Our previous implementation silently returned
430    /// plaintext on failure (`Err(_) => data.to_vec()`), which could expose
431    /// confidential data in the output PDF without any warning. We now panic
432    /// instead, since key sizes are validated at construction time and an error
433    /// here indicates a programming bug, not a recoverable condition.
434    fn encrypt_with_method(&self, data: &[u8], obj_id: ObjectId, cf: CryptFilterMethod) -> Vec<u8> {
435        let iv = Self::generate_iv();
436
437        if self.revision >= 5 {
438            let encrypted = crypto::aes256_cbc_encrypt(&self.encryption_key, &iv, data)
439                .expect("AES-256 encryption failed: key size validated at construction");
440            let mut result = iv.to_vec();
441            result.extend_from_slice(&encrypted);
442            result
443        } else {
444            let object_key = self.compute_object_key(obj_id, cf);
445            match cf {
446                CryptFilterMethod::V2 => crypto::rc4_crypt(&object_key, data),
447                CryptFilterMethod::Aesv2 => {
448                    let encrypted = crypto::aes128_cbc_encrypt(&object_key, &iv, data)
449                        .expect("AES-128 encryption failed: key size validated at construction");
450                    let mut result = iv.to_vec();
451                    result.extend_from_slice(&encrypted);
452                    result
453                }
454                CryptFilterMethod::Aesv3 => {
455                    let encrypted = crypto::aes256_cbc_encrypt(&self.encryption_key, &iv, data)
456                        .expect("AES-256 encryption failed: key size validated at construction");
457                    let mut result = iv.to_vec();
458                    result.extend_from_slice(&encrypted);
459                    result
460                }
461                CryptFilterMethod::None => data.to_vec(),
462            }
463        }
464    }
465
466    /// Generate a cryptographically random 16-byte IV for AES encryption.
467    ///
468    /// # Upstream deviation — IV generation
469    ///
470    /// Upstream PDFium uses C `rand()` (seeded from system state) to fill IVs.
471    /// We use `getrandom` (OS CSPRNG) instead for stronger cryptographic
472    /// guarantees: upstream's `rand()` is not a CSPRNG and its output quality
473    /// varies by platform. Using a true CSPRNG ensures IVs are unpredictable
474    /// across process invocations, which is required for AES-CBC semantic
475    /// security (IND-CPA).
476    fn generate_iv() -> [u8; 16] {
477        let mut iv = [0u8; 16];
478        getrandom::fill(&mut iv).expect("OS RNG unavailable");
479        iv
480    }
481
482    /// Compute the per-object encryption key (Algorithm 1 in PDF spec, R2–R4).
483    ///
484    /// 1. Start with the file encryption key.
485    /// 2. Append the low 3 bytes of the object number (LE).
486    /// 3. Append the low 2 bytes of the generation number (LE).
487    /// 4. If AES (AESV2): append `sAlT` bytes.
488    /// 5. MD5 hash, take first min(key_length + 5, 16) bytes.
489    fn compute_object_key(&self, obj_id: ObjectId, cf: CryptFilterMethod) -> Vec<u8> {
490        let obj_num = obj_id.number;
491        let gen_num = obj_id.generation;
492
493        let mut buf = Vec::with_capacity(self.encryption_key.len() + 9);
494        buf.extend_from_slice(&self.encryption_key);
495        // Object number: 3 bytes LE
496        buf.push((obj_num & 0xFF) as u8);
497        buf.push(((obj_num >> 8) & 0xFF) as u8);
498        buf.push(((obj_num >> 16) & 0xFF) as u8);
499        // Generation number: 2 bytes LE
500        buf.push((gen_num & 0xFF) as u8);
501        buf.push(((gen_num >> 8) & 0xFF) as u8);
502
503        if cf == CryptFilterMethod::Aesv2 {
504            // "sAlT" = 0x73 0x41 0x6C 0x54
505            buf.extend_from_slice(&[0x73, 0x41, 0x6C, 0x54]);
506        }
507
508        let hash = crypto::md5(&buf);
509        let n = std::cmp::min(self.key_length_bytes + 5, 16);
510        hash[..n].to_vec()
511    }
512}
513
514// ---------------------------------------------------------------------------
515// Key derivation (R2–R4) — Algorithm 2
516// ---------------------------------------------------------------------------
517
518/// Encode a UTF-8 password to ISO 8859-1 (Latin-1) for R2-R4 compatibility.
519/// Characters outside the Latin-1 range (>255) are replaced with `?` (0x3F).
520fn encode_password_latin1(password: &str) -> Vec<u8> {
521    password
522        .chars()
523        .map(|c| {
524            let code = c as u32;
525            if code <= 255 {
526                code as u8
527            } else {
528                0x3F // '?'
529            }
530        })
531        .collect()
532}
533
534/// Pad or truncate a password to exactly 32 bytes using PASSWORD_PADDING.
535fn pad_password(password: &[u8]) -> [u8; 32] {
536    let mut padded = [0u8; 32];
537    let copy_len = std::cmp::min(password.len(), 32);
538    padded[..copy_len].copy_from_slice(&password[..copy_len]);
539    if copy_len < 32 {
540        padded[copy_len..].copy_from_slice(&PASSWORD_PADDING[..(32 - copy_len)]);
541    }
542    padded
543}
544
545/// Derive the file encryption key for R2–R4 (PDF spec Algorithm 2).
546fn derive_key_r2_r4(
547    password: &[u8],
548    o_value: &[u8],
549    permissions: i32,
550    file_id: &[u8],
551    revision: u32,
552    key_length_bytes: usize,
553    encrypt_metadata: bool,
554) -> Vec<u8> {
555    let padded = pad_password(password);
556
557    let mut buf = Vec::with_capacity(32 + o_value.len() + 4 + file_id.len() + 4);
558    buf.extend_from_slice(&padded);
559    buf.extend_from_slice(o_value);
560    buf.extend_from_slice(&(permissions as u32).to_le_bytes());
561    buf.extend_from_slice(file_id);
562
563    if revision >= 4 && !encrypt_metadata {
564        buf.extend_from_slice(&[0xFF, 0xFF, 0xFF, 0xFF]);
565    }
566
567    let mut hash = crypto::md5(&buf);
568
569    if revision >= 3 {
570        for _ in 0..50 {
571            hash = crypto::md5(&hash[..key_length_bytes]);
572        }
573    }
574
575    hash[..key_length_bytes].to_vec()
576}
577
578// ---------------------------------------------------------------------------
579// Password verification (R2) — Algorithm 6
580// ---------------------------------------------------------------------------
581
582/// Verify user password for R2 (Algorithm 6).
583fn verify_user_password_r2(key: &[u8], u_value: &[u8]) -> bool {
584    let decrypted = crypto::rc4_crypt(key, u_value);
585    let expected = crypto::md5(&PASSWORD_PADDING);
586    decrypted[..] == expected[..]
587}
588
589// ---------------------------------------------------------------------------
590// Password verification (R3–R4) — Algorithm 7
591// ---------------------------------------------------------------------------
592
593/// Verify user password for R3/R4 (Algorithm 7).
594fn verify_user_password_r3_r4(key: &[u8], u_value: &[u8], file_id: &[u8]) -> bool {
595    // Step a: MD5(PASSWORD_PADDING + file_id)
596    let mut buf = Vec::with_capacity(32 + file_id.len());
597    buf.extend_from_slice(&PASSWORD_PADDING);
598    buf.extend_from_slice(file_id);
599    let hash = crypto::md5(&buf);
600
601    // Step b: RC4 with key
602    let mut result = crypto::rc4_crypt(key, &hash);
603
604    // Step c: 19 rounds of RC4 with modified keys
605    for i in 1..=19u8 {
606        let modified_key: Vec<u8> = key.iter().map(|b| b ^ i).collect();
607        result = crypto::rc4_crypt(&modified_key, &result);
608    }
609
610    // Compare first 16 bytes
611    u_value.len() >= 16 && result.len() >= 16 && result[..16] == u_value[..16]
612}
613
614/// Dispatch to the correct password verification for R2–R4.
615fn verify_user_password_r2_r4(key: &[u8], u_value: &[u8], revision: u32, file_id: &[u8]) -> bool {
616    if revision == 2 {
617        verify_user_password_r2(key, u_value)
618    } else {
619        verify_user_password_r3_r4(key, u_value, file_id)
620    }
621}
622
623// ---------------------------------------------------------------------------
624// Owner password recovery (R2–R4)
625// ---------------------------------------------------------------------------
626
627/// Recover the user password from the O value using the owner password.
628fn recover_user_password_from_owner(
629    owner_password: &[u8],
630    o_value: &[u8],
631    revision: u32,
632    key_length_bytes: usize,
633) -> Vec<u8> {
634    let padded = pad_password(owner_password);
635    let mut hash = crypto::md5(&padded);
636
637    if revision >= 3 {
638        for _ in 0..50 {
639            hash = crypto::md5(&hash[..key_length_bytes]);
640        }
641    }
642
643    let key = &hash[..key_length_bytes];
644
645    if revision == 2 {
646        crypto::rc4_crypt(key, o_value)
647    } else {
648        let mut result = o_value.to_vec();
649        for i in (0..=19u8).rev() {
650            let modified_key: Vec<u8> = key.iter().map(|b| b ^ i).collect();
651            result = crypto::rc4_crypt(&modified_key, &result);
652        }
653        result
654    }
655}
656
657// ---------------------------------------------------------------------------
658// R5/R6 key derivation (ISO 32000-2)
659// ---------------------------------------------------------------------------
660
661/// Derive the file encryption key for R5 (deprecated draft, Adobe extension).
662///
663/// Returns `Some(key)` if either user or owner password matches, else `None`.
664fn derive_key_r5(
665    password: &str,
666    u_value: &[u8],
667    ue_value: &[u8],
668    o_value: &[u8],
669    oe_value: &[u8],
670) -> Result<Option<Vec<u8>>, CryptoError> {
671    let pwd = truncate_utf8_password(password);
672
673    // Try user password: hash(password + Validation Salt from U)
674    if u_value.len() >= 48 && ue_value.len() >= 32 {
675        let validation_salt = &u_value[32..40];
676        let hash = compute_r5_hash(&pwd, validation_salt);
677        if hash[..] == u_value[..32] {
678            // Decrypt UE with hash(password + Key Salt from U)
679            let key_salt = &u_value[40..48];
680            let key_hash = compute_r5_hash(&pwd, key_salt);
681            let file_key = crypto::aes256_cbc_decrypt(&key_hash, &prepend_zero_iv(ue_value))?;
682            return Ok(Some(file_key));
683        }
684    }
685
686    // Try owner password: hash(password + Validation Salt from O + U[0..48])
687    if o_value.len() >= 48 && oe_value.len() >= 32 && u_value.len() >= 48 {
688        let validation_salt = &o_value[32..40];
689        let mut input = Vec::with_capacity(pwd.len() + 8 + 48);
690        input.extend_from_slice(&pwd);
691        input.extend_from_slice(validation_salt);
692        input.extend_from_slice(&u_value[..48]);
693        let hash = crypto::sha256(&input);
694        if hash[..] == o_value[..32] {
695            let key_salt = &o_value[40..48];
696            let mut key_input = Vec::with_capacity(pwd.len() + 8 + 48);
697            key_input.extend_from_slice(&pwd);
698            key_input.extend_from_slice(key_salt);
699            key_input.extend_from_slice(&u_value[..48]);
700            let key_hash = crypto::sha256(&key_input);
701            let file_key = crypto::aes256_cbc_decrypt(&key_hash, &prepend_zero_iv(oe_value))?;
702            return Ok(Some(file_key));
703        }
704    }
705
706    Ok(None)
707}
708
709/// Derive the file encryption key for R6 (ISO 32000-2, Algorithm 2.A).
710///
711/// R6 uses Algorithm 2.B (iterative hash) instead of simple SHA-256.
712fn derive_key_r6(
713    password: &str,
714    u_value: &[u8],
715    ue_value: &[u8],
716    o_value: &[u8],
717    oe_value: &[u8],
718) -> Result<Option<Vec<u8>>, CryptoError> {
719    let pwd = truncate_utf8_password(password);
720
721    // Try user password: compute_r6_hash(password, validation_salt, "")
722    if u_value.len() >= 48 && ue_value.len() >= 32 {
723        let validation_salt = &u_value[32..40];
724        let hash = compute_r6_hash(&pwd, validation_salt, &[]);
725        if hash[..] == u_value[..32] {
726            // Decrypt UE with hash(password, key_salt, "")
727            let key_salt = &u_value[40..48];
728            let key_hash = compute_r6_hash(&pwd, key_salt, &[]);
729            let file_key = crypto::aes256_cbc_decrypt(&key_hash, &prepend_zero_iv(ue_value))?;
730            return Ok(Some(file_key));
731        }
732    }
733
734    // Try owner password: compute_r6_hash(password, validation_salt, U[0..48])
735    if o_value.len() >= 48 && oe_value.len() >= 32 && u_value.len() >= 48 {
736        let validation_salt = &o_value[32..40];
737        let hash = compute_r6_hash(&pwd, validation_salt, &u_value[..48]);
738        if hash[..] == o_value[..32] {
739            let key_salt = &o_value[40..48];
740            let key_hash = compute_r6_hash(&pwd, key_salt, &u_value[..48]);
741            let file_key = crypto::aes256_cbc_decrypt(&key_hash, &prepend_zero_iv(oe_value))?;
742            return Ok(Some(file_key));
743        }
744    }
745
746    Ok(None)
747}
748
749/// Interpret the first 16 bytes of `bytes` as a big-endian 128-bit integer and return it mod 3.
750fn big_endian_mod3(bytes: &[u8]) -> u32 {
751    bytes
752        .iter()
753        .take(16)
754        .fold(0u32, |acc, &b| (acc * 256 + b as u32) % 3)
755}
756
757/// ISO 32000-2 Algorithm 2.B — compute hash for R6 encryption.
758///
759/// This implements the iterative hash algorithm that uses SHA-256, SHA-384,
760/// and SHA-512 in a loop until convergence.
761fn compute_r6_hash(password: &[u8], salt: &[u8], u_value: &[u8]) -> [u8; 32] {
762    // Step a: K = SHA-256(password || salt || u_value)
763    let mut input = Vec::with_capacity(password.len() + salt.len() + u_value.len());
764    input.extend_from_slice(password);
765    input.extend_from_slice(salt);
766    input.extend_from_slice(u_value);
767    let mut k = crypto::sha256(&input);
768
769    let mut round: u32 = 0;
770    loop {
771        // Step b: K1 = (password || K || u_value) repeated 64 times
772        let sequence_len = password.len() + k.len() + u_value.len();
773        let mut k1 = Vec::with_capacity(sequence_len * 64);
774        for _ in 0..64 {
775            k1.extend_from_slice(password);
776            k1.extend_from_slice(&k);
777            k1.extend_from_slice(u_value);
778        }
779
780        // Step c: E = AES-128-CBC(K[0..16], K[16..32], K1)
781        let aes_key = &k[..16];
782        let aes_iv = &k[16..32];
783        // Key is always 16 bytes (from SHA-256 hash), IV is always 16 bytes.
784        let e = crypto::aes128_cbc_encrypt(aes_key, aes_iv, &k1)
785            .expect("AES-128-CBC key/IV from SHA-256 are always valid");
786
787        // Step d: Select hash based on big-endian 128-bit value of first 16 bytes mod 3
788        let hash_select = big_endian_mod3(&e);
789
790        // Step e: K = selected_hash(E)
791        match hash_select {
792            0 => {
793                let h = crypto::sha256(&e);
794                k = h;
795            }
796            1 => {
797                let h = crypto::sha384(&e);
798                k.copy_from_slice(&h[..32]);
799            }
800            _ => {
801                let h = crypto::sha512(&e);
802                k.copy_from_slice(&h[..32]);
803            }
804        }
805
806        // Step f: if round >= 64, check last byte of E
807        if round >= 64 {
808            let last_byte = *e.last().unwrap_or(&0);
809            if last_byte <= (round - 32) as u8 {
810                break;
811            }
812        }
813
814        round += 1;
815
816        // Safety limit to prevent infinite loops on malformed data
817        if round >= 1000 {
818            break;
819        }
820    }
821
822    k
823}
824
825/// Compute R5 hash: SHA-256(password + salt).
826fn compute_r5_hash(password: &[u8], salt: &[u8]) -> [u8; 32] {
827    let mut input = Vec::with_capacity(password.len() + salt.len());
828    input.extend_from_slice(password);
829    input.extend_from_slice(salt);
830    crypto::sha256(&input)
831}
832
833/// Truncate a UTF-8 password to at most 127 bytes (R5/R6 spec).
834fn truncate_utf8_password(password: &str) -> Vec<u8> {
835    let bytes = password.as_bytes();
836    if bytes.len() <= 127 {
837        bytes.to_vec()
838    } else {
839        bytes[..127].to_vec()
840    }
841}
842
843/// Prepend a zero IV (16 bytes of 0x00) for AES-256 decryption of UE/OE.
844fn prepend_zero_iv(data: &[u8]) -> Vec<u8> {
845    let mut result = vec![0u8; 16];
846    result.extend_from_slice(data);
847    result
848}
849
850// ---------------------------------------------------------------------------
851// Crypt filter method parsing
852// ---------------------------------------------------------------------------
853
854/// Parse a single crypt filter from the encryption dictionary by filter key name
855/// (e.g. /StmF or /StrF). Looks up the named filter in /CF to determine the method.
856fn parse_single_crypt_filter<S: PdfSource>(
857    encrypt_dict: &HashMap<Name, Object>,
858    store: &ObjectStore<S>,
859    filter_key: &Name,
860) -> CryptFilterMethod {
861    let filter_name = encrypt_dict
862        .get(filter_key)
863        .and_then(|obj| store.deep_resolve(obj).ok())
864        .and_then(|obj| obj.as_name())
865        .cloned()
866        .unwrap_or_else(|| Name::from("StdCF"));
867
868    if filter_name == Name::from("Identity") {
869        return CryptFilterMethod::None;
870    }
871
872    // Look up the filter in /CF dict
873    let cf_dict = encrypt_dict
874        .get(&Name::cf())
875        .and_then(|obj| store.deep_resolve(obj).ok())
876        .and_then(|obj| obj.as_dict());
877
878    if let Some(cf) = cf_dict {
879        if let Some(filter_obj) = cf.get(&filter_name) {
880            if let Ok(filter_resolved) = store.deep_resolve(filter_obj) {
881                if let Some(filter_dict) = filter_resolved.as_dict() {
882                    let method = filter_dict
883                        .get(&Name::cfm())
884                        .and_then(|obj| store.deep_resolve(obj).ok())
885                        .and_then(|obj| obj.as_name())
886                        .cloned();
887
888                    if let Some(m) = method {
889                        if m == Name::aesv2() {
890                            return CryptFilterMethod::Aesv2;
891                        } else if m == Name::aesv3() {
892                            return CryptFilterMethod::Aesv3;
893                        } else if m == Name::v2() {
894                            return CryptFilterMethod::V2;
895                        } else if m == Name::none() {
896                            return CryptFilterMethod::None;
897                        }
898                    }
899                }
900            }
901        }
902    }
903
904    // Default: RC4 for V4
905    CryptFilterMethod::V2
906}
907
908// ---------------------------------------------------------------------------
909// Dictionary helpers
910// ---------------------------------------------------------------------------
911
912fn get_int<S: PdfSource>(
913    dict: &HashMap<Name, Object>,
914    store: &ObjectStore<S>,
915    key: &Name,
916) -> Result<i64, SecurityError> {
917    dict.get(key)
918        .and_then(|obj| store.deep_resolve(obj).ok())
919        .and_then(|obj| obj.as_i64())
920        .ok_or_else(|| SecurityError::MissingKey(key.to_string()))
921}
922
923fn get_optional_int<S: PdfSource>(
924    dict: &HashMap<Name, Object>,
925    store: &ObjectStore<S>,
926    key: &Name,
927) -> Option<i64> {
928    dict.get(key)
929        .and_then(|obj| store.deep_resolve(obj).ok())
930        .and_then(|obj| obj.as_i64())
931}
932
933fn get_optional_bool<S: PdfSource>(
934    dict: &HashMap<Name, Object>,
935    store: &ObjectStore<S>,
936    key: &Name,
937) -> Option<bool> {
938    dict.get(key)
939        .and_then(|obj| store.deep_resolve(obj).ok())
940        .and_then(|obj| obj.as_bool())
941}
942
943fn get_string_bytes<S: PdfSource>(
944    dict: &HashMap<Name, Object>,
945    store: &ObjectStore<S>,
946    key: &Name,
947) -> Result<Vec<u8>, SecurityError> {
948    dict.get(key)
949        .and_then(|obj| store.deep_resolve(obj).ok())
950        .and_then(|obj| obj.as_string())
951        .map(|s| s.as_bytes().to_vec())
952        .ok_or_else(|| SecurityError::MissingKey(key.to_string()))
953}
954
955#[cfg(test)]
956mod tests {
957    use super::*;
958
959    #[test]
960    fn password_padding_empty() {
961        let padded = pad_password(b"");
962        assert_eq!(padded, PASSWORD_PADDING);
963    }
964
965    #[test]
966    fn password_padding_short() {
967        let padded = pad_password(b"test");
968        assert_eq!(&padded[..4], b"test");
969        assert_eq!(&padded[4..], &PASSWORD_PADDING[..28]);
970    }
971
972    #[test]
973    fn password_padding_exact_32() {
974        let pwd = b"abcdefghijklmnopqrstuvwxyz012345"; // 32 bytes
975        let padded = pad_password(pwd);
976        assert_eq!(&padded[..], &pwd[..]);
977    }
978
979    #[test]
980    fn password_padding_longer_than_32() {
981        let pwd = b"abcdefghijklmnopqrstuvwxyz0123456789"; // 36 bytes
982        let padded = pad_password(pwd);
983        assert_eq!(&padded[..], &pwd[..32]);
984    }
985
986    #[test]
987    fn key_derivation_r2_known() {
988        // Use empty password, known O value, P=-44, known file_id
989        let o_value = [0u8; 32];
990        let file_id = b"test_file_id_123";
991        let key = derive_key_r2_r4(b"", &o_value, -44, file_id, 2, 5, true);
992        assert_eq!(key.len(), 5);
993        // Verify the key is deterministic
994        let key2 = derive_key_r2_r4(b"", &o_value, -44, file_id, 2, 5, true);
995        assert_eq!(key, key2);
996    }
997
998    #[test]
999    fn key_derivation_r3_known() {
1000        let o_value = [0u8; 32];
1001        let file_id = b"test_file_id_123";
1002        let key = derive_key_r2_r4(b"", &o_value, -44, file_id, 3, 16, true);
1003        assert_eq!(key.len(), 16);
1004        // R3 applies 50 additional MD5 rounds — key should differ from R2
1005        let key_r2 = derive_key_r2_r4(b"", &o_value, -44, file_id, 2, 5, true);
1006        assert_ne!(key[..5], key_r2[..]);
1007    }
1008
1009    #[test]
1010    fn user_password_verification_r2_round_trip() {
1011        // Derive a key, compute the expected U value, then verify
1012        let o_value = [0x42u8; 32];
1013        let file_id = b"abcdef0123456789";
1014        let key = derive_key_r2_r4(b"password", &o_value, -4, file_id, 2, 5, true);
1015
1016        // Compute U: RC4-encrypt MD5(PASSWORD_PADDING) with key
1017        let expected_u = crypto::rc4_crypt(&key, &crypto::md5(&PASSWORD_PADDING));
1018        assert!(verify_user_password_r2(&key, &expected_u));
1019    }
1020
1021    #[test]
1022    fn user_password_verification_r2_wrong_password() {
1023        let o_value = [0x42u8; 32];
1024        let file_id = b"abcdef0123456789";
1025        let key = derive_key_r2_r4(b"password", &o_value, -4, file_id, 2, 5, true);
1026        let expected_u = crypto::rc4_crypt(&key, &crypto::md5(&PASSWORD_PADDING));
1027
1028        // Wrong password yields different key
1029        let wrong_key = derive_key_r2_r4(b"wrong", &o_value, -4, file_id, 2, 5, true);
1030        assert!(!verify_user_password_r2(&wrong_key, &expected_u));
1031    }
1032
1033    #[test]
1034    fn user_password_verification_r3_round_trip() {
1035        let o_value = [0x42u8; 32];
1036        let file_id = b"abcdef0123456789";
1037        let key = derive_key_r2_r4(b"pass", &o_value, -4, file_id, 3, 16, true);
1038
1039        // Compute U for R3: MD5(PADDING + file_id), then 20 rounds of RC4
1040        let mut buf = Vec::new();
1041        buf.extend_from_slice(&PASSWORD_PADDING);
1042        buf.extend_from_slice(file_id);
1043        let hash = crypto::md5(&buf);
1044
1045        let mut result = crypto::rc4_crypt(&key, &hash);
1046        for i in 1..=19u8 {
1047            let modified_key: Vec<u8> = key.iter().map(|b| b ^ i).collect();
1048            result = crypto::rc4_crypt(&modified_key, &result);
1049        }
1050        // Pad U to 32 bytes (remaining bytes are random, but first 16 matter)
1051        let mut u_value = result;
1052        u_value.resize(32, 0);
1053
1054        assert!(verify_user_password_r3_r4(&key, &u_value, file_id));
1055    }
1056
1057    #[test]
1058    fn object_key_computation() {
1059        let handler = SecurityHandler {
1060            revision: 3,
1061            key_length_bytes: 5,
1062            encryption_key: vec![0x01, 0x02, 0x03, 0x04, 0x05],
1063            permissions: Permissions::from_bits(-4),
1064            encrypt_metadata: true,
1065            stream_cf: CryptFilterMethod::V2,
1066            string_cf: CryptFilterMethod::V2,
1067            o_value: Vec::new(),
1068            u_value: Vec::new(),
1069        };
1070
1071        let obj_id = ObjectId::new(10, 0);
1072        let key = handler.compute_object_key(obj_id, CryptFilterMethod::V2);
1073
1074        // key_length + 5 = 10, but min(10, 16) = 10
1075        assert_eq!(key.len(), 10);
1076
1077        // Verify deterministic
1078        let key2 = handler.compute_object_key(obj_id, CryptFilterMethod::V2);
1079        assert_eq!(key, key2);
1080
1081        // Different object ID should yield different key
1082        let key3 = handler.compute_object_key(ObjectId::new(11, 0), CryptFilterMethod::V2);
1083        assert_ne!(key, key3);
1084    }
1085
1086    #[test]
1087    fn object_key_aesv2_includes_salt() {
1088        let handler = SecurityHandler {
1089            revision: 4,
1090            key_length_bytes: 16,
1091            encryption_key: vec![0xAA; 16],
1092            permissions: Permissions::from_bits(-4),
1093            encrypt_metadata: true,
1094            stream_cf: CryptFilterMethod::Aesv2,
1095            string_cf: CryptFilterMethod::V2,
1096            o_value: Vec::new(),
1097            u_value: Vec::new(),
1098        };
1099
1100        let obj_id = ObjectId::new(1, 0);
1101        let key_rc4 = handler.compute_object_key(obj_id, CryptFilterMethod::V2);
1102        let key_aes = handler.compute_object_key(obj_id, CryptFilterMethod::Aesv2);
1103
1104        // AES key should differ because of "sAlT" suffix
1105        assert_ne!(key_rc4, key_aes);
1106    }
1107
1108    #[test]
1109    fn decrypt_string_rc4_round_trip() {
1110        let handler = SecurityHandler {
1111            revision: 3,
1112            key_length_bytes: 5,
1113            encryption_key: vec![0x01, 0x02, 0x03, 0x04, 0x05],
1114            permissions: Permissions::from_bits(-4),
1115            encrypt_metadata: true,
1116            stream_cf: CryptFilterMethod::V2,
1117            string_cf: CryptFilterMethod::V2,
1118            o_value: Vec::new(),
1119            u_value: Vec::new(),
1120        };
1121
1122        let obj_id = ObjectId::new(1, 0);
1123        let plaintext = b"Hello, encrypted world!";
1124
1125        // Encrypt (RC4 is symmetric, so encrypt = decrypt)
1126        let object_key = handler.compute_object_key(obj_id, handler.string_cf);
1127        let encrypted = crypto::rc4_crypt(&object_key, plaintext);
1128
1129        // Decrypt via handler
1130        let decrypted = handler.decrypt_string(&encrypted, obj_id);
1131        assert_eq!(decrypted, plaintext);
1132    }
1133
1134    #[test]
1135    fn crypt_filter_method_none_passthrough() {
1136        let handler = SecurityHandler {
1137            revision: 4,
1138            key_length_bytes: 16,
1139            encryption_key: vec![0; 16],
1140            permissions: Permissions::from_bits(-4),
1141            encrypt_metadata: true,
1142            stream_cf: CryptFilterMethod::None,
1143            string_cf: CryptFilterMethod::None,
1144            o_value: Vec::new(),
1145            u_value: Vec::new(),
1146        };
1147
1148        let data = b"unencrypted data";
1149        let obj_id = ObjectId::new(1, 0);
1150        assert_eq!(handler.decrypt_string(data, obj_id), data);
1151        assert_eq!(handler.decrypt_stream(data, obj_id), data);
1152    }
1153
1154    #[test]
1155    fn truncate_utf8_password_short() {
1156        let pwd = truncate_utf8_password("hello");
1157        assert_eq!(pwd, b"hello");
1158    }
1159
1160    #[test]
1161    fn truncate_utf8_password_long() {
1162        let long_pwd = "a".repeat(200);
1163        let pwd = truncate_utf8_password(&long_pwd);
1164        assert_eq!(pwd.len(), 127);
1165    }
1166
1167    #[test]
1168    fn compute_r6_hash_basic() {
1169        // Verify that compute_r6_hash returns a deterministic 32-byte result
1170        let hash = compute_r6_hash(b"password", &[0u8; 8], &[]);
1171        assert_eq!(hash.len(), 32);
1172        // Same input should produce same output
1173        let hash2 = compute_r6_hash(b"password", &[0u8; 8], &[]);
1174        assert_eq!(hash, hash2);
1175    }
1176
1177    #[test]
1178    fn compute_r6_hash_differs_from_simple_sha256() {
1179        // R6 iterative hash should differ from simple SHA-256
1180        let salt = [0x01u8; 8];
1181        let r6_hash = compute_r6_hash(b"test", &salt, &[]);
1182        let simple_hash = crypto::sha256(&{
1183            let mut v = b"test".to_vec();
1184            v.extend_from_slice(&salt);
1185            v
1186        });
1187        // The iterative hash should produce a different result than simple SHA-256
1188        // (because it goes through multiple rounds with AES + different hash functions)
1189        assert_ne!(r6_hash, simple_hash);
1190    }
1191
1192    #[test]
1193    fn compute_r6_hash_with_u_value() {
1194        // Hash with non-empty u_value should differ from empty u_value
1195        let salt = [0x42u8; 8];
1196        let hash_no_u = compute_r6_hash(b"pwd", &salt, &[]);
1197        let hash_with_u = compute_r6_hash(b"pwd", &salt, &[0xAAu8; 48]);
1198        assert_ne!(hash_no_u, hash_with_u);
1199    }
1200
1201    #[test]
1202    fn r6_user_password_round_trip() {
1203        // Simulate creating R6 encryption data and verifying it
1204        let password = b"test123";
1205        let validation_salt = [0x11u8; 8];
1206        let key_salt = [0x22u8; 8];
1207        let file_key = [0x42u8; 32]; // the actual file encryption key
1208
1209        // Compute U value: hash(password, validation_salt) || validation_salt || key_salt
1210        let u_hash = compute_r6_hash(password, &validation_salt, &[]);
1211        let mut u_value = Vec::with_capacity(48);
1212        u_value.extend_from_slice(&u_hash);
1213        u_value.extend_from_slice(&validation_salt);
1214        u_value.extend_from_slice(&key_salt);
1215
1216        // Compute UE: AES-256-CBC encrypt file_key with hash(password, key_salt)
1217        let key_hash = compute_r6_hash(password, &key_salt, &[]);
1218        let iv = [0u8; 16];
1219        let ue_value = crypto::aes256_cbc_encrypt(&key_hash, &iv, &file_key).unwrap();
1220
1221        // Now verify: derive_key_r6 should recover the file key
1222        let result = derive_key_r6(
1223            "test123", &u_value, &ue_value, &[0u8; 48], // dummy O
1224            &[0u8; 32], // dummy OE
1225        )
1226        .unwrap();
1227
1228        assert!(result.is_some());
1229        assert_eq!(result.unwrap(), file_key);
1230    }
1231
1232    #[test]
1233    fn r6_wrong_password_returns_none() {
1234        let password = b"correct";
1235        let validation_salt = [0x33u8; 8];
1236        let key_salt = [0x44u8; 8];
1237
1238        let u_hash = compute_r6_hash(password, &validation_salt, &[]);
1239        let mut u_value = Vec::with_capacity(48);
1240        u_value.extend_from_slice(&u_hash);
1241        u_value.extend_from_slice(&validation_salt);
1242        u_value.extend_from_slice(&key_salt);
1243
1244        let key_hash = compute_r6_hash(password, &key_salt, &[]);
1245        let ue_value = crypto::aes256_cbc_encrypt(&key_hash, &[0u8; 16], &[0u8; 32]).unwrap();
1246
1247        // Wrong password should not match
1248        let result = derive_key_r6("wrong", &u_value, &ue_value, &[0u8; 48], &[0u8; 32]).unwrap();
1249
1250        assert!(result.is_none());
1251    }
1252
1253    #[test]
1254    fn owner_password_recovery_r2() {
1255        // Set up: compute O from a known user password + owner password
1256        let user_pwd = b"user";
1257        let owner_pwd = b"owner";
1258        let key_len = 5;
1259
1260        // Compute O value: pad owner_pwd, MD5, RC4-encrypt padded user_pwd
1261        let padded_owner = pad_password(owner_pwd);
1262        let hash = crypto::md5(&padded_owner);
1263        let owner_key = &hash[..key_len];
1264        let padded_user = pad_password(user_pwd);
1265        let o_value = crypto::rc4_crypt(owner_key, &padded_user);
1266
1267        // Now recover
1268        let recovered = recover_user_password_from_owner(owner_pwd, &o_value, 2, key_len);
1269        assert_eq!(&recovered[..], &padded_user[..]);
1270    }
1271
1272    // -----------------------------------------------------------------------
1273    // P0-1: Verify PASSWORD_PADDING matches PDF spec byte-by-byte
1274    // -----------------------------------------------------------------------
1275
1276    #[test]
1277    fn password_padding_matches_pdf_spec() {
1278        // Table 3.18 / ISO 32000-1:2008 section 7.6.3.3
1279        let spec_padding: [u8; 32] = [
1280            0x28, 0xBF, 0x4E, 0x5E, 0x4E, 0x75, 0x8A, 0x41, 0x64, 0x00, 0x4E, 0x56, 0xFF, 0xFA,
1281            0x01, 0x08, 0x2E, 0x2E, 0x00, 0xB6, 0xD0, 0x68, 0x3E, 0x80, 0x2F, 0x0C, 0xA9, 0xFE,
1282            0x64, 0x53, 0x69, 0x7A,
1283        ];
1284        assert_eq!(PASSWORD_PADDING, spec_padding);
1285    }
1286
1287    // -----------------------------------------------------------------------
1288    // P0-2: Test big-endian mod 3 vs sum mod 3 divergence
1289    // -----------------------------------------------------------------------
1290
1291    #[test]
1292    fn big_endian_mod3_basic() {
1293        // All zeros: 0 mod 3 = 0
1294        assert_eq!(big_endian_mod3(&[0u8; 16]), 0);
1295        // All 0xFF: large number mod 3
1296        assert_eq!(big_endian_mod3(&[0xFF; 16]), big_endian_mod3(&[0xFF; 16]));
1297    }
1298
1299    #[test]
1300    fn big_endian_mod3_differs_from_sum_mod3() {
1301        // Find a value where sum%3 differs from big-endian%3
1302        // bytes = [0x01, 0x00, ...0x00] (15 zeros after):
1303        //   sum   = 1, 1 % 3 = 1
1304        //   big-endian = 256^15 mod 3. Since 256 mod 3 = 1, 256^15 mod 3 = 1. Same.
1305        // Try [0x02, 0x01, 0, ...]:
1306        //   sum   = 3, 3 % 3 = 0
1307        //   big-endian = 2*256 + 1 = 513 mod 3 = 0. Same.
1308        // Try [0x80, 0x00, ...0x00, 0x01]:
1309        //   sum   = 0x80 + 1 = 129, 129 % 3 = 0
1310        //   big-endian = 0x80 * 256^15 + 1. Since 256 mod 3 = 1: 128*1 + 1 = 129 mod 3 = 0. Same.
1311        // Try [3, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 2]:
1312        //   sum = 5, 5%3 = 2
1313        //   big-endian = 3*256^15 + 2. 256^15 mod 3 = 1, so 3+2=5 mod 3 = 2. Same.
1314        // Actually the two methods differ when the positional weights matter.
1315        // [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 2, 0]:
1316        //   sum = 2, 2%3 = 2
1317        //   big-endian: 2*256 = 512. 512%3 = 2. Same.
1318        // [0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1, 1]:
1319        //   sum = 2, 2%3 = 2
1320        //   big-endian: 1*256+1 = 257. 257%3 = 2. Same.
1321        // Since 256 mod 3 = 1, positional weighting doesn't change mod3 result.
1322        // So sum%3 == big-endian%3 for mod 3 specifically.
1323        // However, the spec says to interpret as big-endian, so our implementation is still correct.
1324        // Let's just verify the function works correctly on known values.
1325        let bytes = [0u8, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 1];
1326        assert_eq!(big_endian_mod3(&bytes), 1);
1327        let bytes = [0u8, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 2];
1328        assert_eq!(big_endian_mod3(&bytes), 2);
1329        let bytes = [0u8, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 0, 3];
1330        assert_eq!(big_endian_mod3(&bytes), 0);
1331    }
1332
1333    // -----------------------------------------------------------------------
1334    // P2-31: Test separate StrF/StmF
1335    // -----------------------------------------------------------------------
1336
1337    #[test]
1338    fn separate_strf_stmf_decrypt() {
1339        // Create a handler where streams use AES but strings use RC4
1340        let handler = SecurityHandler {
1341            revision: 4,
1342            key_length_bytes: 16,
1343            encryption_key: vec![0xBB; 16],
1344            permissions: Permissions::from_bits(-4),
1345            encrypt_metadata: true,
1346            stream_cf: CryptFilterMethod::Aesv2,
1347            string_cf: CryptFilterMethod::V2,
1348            o_value: Vec::new(),
1349            u_value: Vec::new(),
1350        };
1351
1352        // Verify accessor returns stream_cf
1353        assert_eq!(handler.crypt_filter_method(), CryptFilterMethod::Aesv2);
1354
1355        let obj_id = ObjectId::new(1, 0);
1356
1357        // String uses RC4 (V2) — round-trip
1358        let plaintext = b"hello";
1359        let obj_key_str = handler.compute_object_key(obj_id, CryptFilterMethod::V2);
1360        let encrypted_str = crypto::rc4_crypt(&obj_key_str, plaintext);
1361        let decrypted = handler.decrypt_string(&encrypted_str, obj_id);
1362        assert_eq!(decrypted, plaintext);
1363
1364        // Stream uses AESV2 — verify the object key includes sAlT
1365        let obj_key_stm = handler.compute_object_key(obj_id, CryptFilterMethod::Aesv2);
1366        assert_ne!(obj_key_str, obj_key_stm); // sAlT suffix makes them differ
1367    }
1368
1369    // -----------------------------------------------------------------------
1370    // P2-32: Test Latin-1 password encoding
1371    // -----------------------------------------------------------------------
1372
1373    #[test]
1374    fn encode_password_latin1_ascii() {
1375        let encoded = encode_password_latin1("hello");
1376        assert_eq!(encoded, b"hello");
1377    }
1378
1379    #[test]
1380    fn encode_password_latin1_latin_chars() {
1381        // e-acute (U+00E9) is within Latin-1 range
1382        let encoded = encode_password_latin1("\u{00E9}");
1383        assert_eq!(encoded, vec![0xE9]);
1384    }
1385
1386    #[test]
1387    fn encode_password_latin1_non_latin() {
1388        // CJK character (U+4E2D) is outside Latin-1 range, replaced with '?'
1389        let encoded = encode_password_latin1("\u{4E2D}");
1390        assert_eq!(encoded, vec![0x3F]);
1391    }
1392
1393    #[test]
1394    fn encode_password_latin1_mixed() {
1395        // Mix of ASCII, Latin-1, and non-Latin-1
1396        let encoded = encode_password_latin1("a\u{00FC}\u{4E2D}b");
1397        assert_eq!(encoded, vec![b'a', 0xFC, 0x3F, b'b']);
1398    }
1399
1400    // -----------------------------------------------------------------------
1401    // P2-33: Test /Perms validation
1402    // -----------------------------------------------------------------------
1403
1404    #[test]
1405    fn encode_password_latin1_empty() {
1406        let encoded = encode_password_latin1("");
1407        assert!(encoded.is_empty());
1408    }
1409
1410    #[test]
1411    fn encode_password_latin1_ascii_alphanumeric() {
1412        let encoded = encode_password_latin1("ABC123");
1413        assert_eq!(encoded, b"ABC123");
1414    }
1415
1416    #[test]
1417    fn encode_password_latin1_0xff() {
1418        // U+00FF (y-diaeresis) is the last character in Latin-1 range
1419        let encoded = encode_password_latin1("\u{00FF}");
1420        assert_eq!(encoded, vec![0xFF]);
1421    }
1422
1423    #[test]
1424    fn encode_password_latin1_over_range() {
1425        // U+0100 (Latin Extended-A) is just outside Latin-1 range
1426        let encoded = encode_password_latin1("\u{0100}");
1427        assert_eq!(encoded, vec![0x3F]); // '?' fallback
1428    }
1429
1430    #[test]
1431    fn truncate_utf8_password_empty() {
1432        let pwd = truncate_utf8_password("");
1433        assert!(pwd.is_empty());
1434    }
1435
1436    #[test]
1437    fn truncate_utf8_password_exact_127() {
1438        let input = "a".repeat(127);
1439        let pwd = truncate_utf8_password(&input);
1440        assert_eq!(pwd.len(), 127);
1441        assert_eq!(pwd, input.as_bytes());
1442    }
1443
1444    #[test]
1445    fn truncate_utf8_password_over_127() {
1446        let input = "a".repeat(128);
1447        let pwd = truncate_utf8_password(&input);
1448        assert_eq!(pwd.len(), 127);
1449    }
1450
1451    #[test]
1452    fn perms_validation_construct_and_verify() {
1453        // Build a valid /Perms block per PDF spec Algorithm 2.A:
1454        //   [0..4]  = /P value as LE i32
1455        //   [8]     = 'T' (EncryptMetadata=true) or 'F'
1456        //   [9..12] = "adb"
1457        let permissions: i32 = -4;
1458        let mut perms_plain = [0u8; 16];
1459        perms_plain[0..4].copy_from_slice(&permissions.to_le_bytes());
1460        // Bytes 4-7: can be anything
1461        perms_plain[8] = b'T'; // EncryptMetadata flag
1462        perms_plain[9] = b'a';
1463        perms_plain[10] = b'd';
1464        perms_plain[11] = b'b';
1465
1466        // Encrypt with AES-256-ECB (single block, no padding)
1467        let file_key = [0x42u8; 32];
1468        // Use aes256_ecb_encrypt_block equivalent: encrypt then decrypt round-trip
1469        // For this test, we encrypt using the raw AES block cipher
1470        use aes::cipher::{BlockEncrypt, KeyInit};
1471        let cipher = aes::Aes256::new_from_slice(&file_key).unwrap();
1472        let mut block = aes::cipher::generic_array::GenericArray::clone_from_slice(&perms_plain);
1473        cipher.encrypt_block(&mut block);
1474        let encrypted_perms: [u8; 16] = block.into();
1475
1476        // Now decrypt and validate (simulating what from_encrypt_dict does)
1477        let decrypted = crypto::aes256_ecb_decrypt_block(&file_key, &encrypted_perms).unwrap();
1478
1479        // Byte 8 = 'T' (EncryptMetadata), bytes 9-11 = "adb"
1480        assert_eq!(decrypted[8], b'T');
1481        assert_eq!(&decrypted[9..12], b"adb");
1482        let recovered_p =
1483            i32::from_le_bytes([decrypted[0], decrypted[1], decrypted[2], decrypted[3]]);
1484        assert_eq!(recovered_p, permissions);
1485    }
1486}