
symmetric-cipher-attacks
Symmetric cipher attack playbook. Use when exploiting block cipher mode weaknesses (CBC padding oracle, ECB cut-and-paste, bit flipping), stream cipher key reuse, or meet-in-the-middle attacks.
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Install
Works with every agent the skills CLI supports.
npx skills add https://github.com/yaklang/hack-skills --skill symmetric-cipher-attacks- 01
Install
Run the command in your project. The CLI asks which agents to install for.
- 02
Describe the task
Ask your agent for something this skill covers. It loads symmetric-cipher-attacks automatically when relevant.
- 03
Review the result
The agent follows the SKILL.md steps, scripts and references bundled with the skill.
SKILL.md
The instructions your agent reads when the skill is triggered.
SKILL: Symmetric Cipher Attacks — Expert Cryptanalysis Playbook
AI LOAD INSTRUCTION: Expert techniques for attacking symmetric encryption in CTF and authorized testing. Covers CBC padding oracle, CBC bit flipping, ECB detection and exploitation, stream cipher key reuse, LFSR/LCG state recovery, RC4 biases, and meet-in-the-middle attacks. Base models often confuse ECB and CBC attack strategies or fail to set up byte-at-a-time ECB decryption correctly.
0. RELATED ROUTING
- rsa-attack-techniques when symmetric key is protected by RSA
- hash-attack-techniques when HMAC or hash-based authentication is involved
- lattice-crypto-attacks for LCG/LFSR state recovery via lattice methods
Advanced Reference
Also load BLOCK_CIPHER_ATTACKS.md when you need:
- Detailed attack scripts with full Python implementations
- Step-by-step byte-at-a-time ECB walkthrough
- PadBuster usage and custom padding oracle scripts
- LCG/LFSR recovery implementation
Quick attack selection
| Observable Behavior | Likely Weakness | Attack |
|---|---|---|
| Same plaintext → same ciphertext (block-aligned) | ECB mode | Cut-and-paste / byte-at-a-time |
| Padding error distinguishable | CBC padding oracle | Decrypt without key |
| Can modify ciphertext, affects next block | CBC mode, no integrity check | Bit flipping |
| Key reused with XOR/stream cipher | Two-time pad | XOR ciphertexts together |
| Predictable PRNG output | LCG or LFSR | State recovery |
| Double encryption used | 2DES-like | Meet in the middle |
1. PADDING ORACLE ATTACK (CBC MODE)
1.1 Mechanism
CBC decryption: P_i = D_K(C_i) ⊕ C_{i-1}
If the server reveals whether padding is valid (PKCS#7), we can decrypt any block by manipulating the previous ciphertext block.
1.2 Attack Steps
Target: decrypt block C_i (with unknown plaintext P_i)
For byte position b = 15 down to 0 (last byte first):
padding_value = 16 - b
For guess = 0x00 to 0xFF:
Construct modified C'_{i-1}:
- Bytes 0..b-1: original C_{i-1} bytes
- Byte b: guess
- Bytes b+1..15: calculated to produce correct padding
Send (C'_{i-1} || C_i) to oracle
If oracle says "valid padding":
intermediate_byte[b] = guess ⊕ padding_value
plaintext_byte[b] = intermediate_byte[b] ⊕ original_C_{i-1}[b]
1.3 Python Implementation
def padding_oracle_attack(ciphertext, block_size, oracle):
"""
oracle(ct) returns True if padding is valid, False otherwise.
ciphertext includes IV as first block.
"""
blocks = [ciphertext[i:i+block_size] for i in range(0, len(ciphertext), block_size)]
plaintext = b""
for block_idx in range(1, len(blocks)):
prev_block = bytearray(blocks[block_idx - 1])
curr_block = blocks[block_idx]
intermediate = [0] * block_size
decrypted = [0] * block_size
for byte_pos in range(block_size - 1, -1, -1):
padding_val = block_size - byte_pos
for guess in range(256):
modified = bytearray(block_size)
modified[byte_pos] = guess
for j in range(byte_pos + 1, block_size):
modified[j] = intermediate[j] ^ padding_val
test_ct = bytes(modified) + curr_block
if oracle(test_ct):
if byte_pos == block_size - 1:
# Verify it's not a false positive (padding 0x02 0x02)
check = bytearray(modified)
check[byte_pos - 1] ^= 1
if not oracle(bytes(check) + curr_block):
continue
intermediate[byte_pos] = guess ^ padding_val
decrypted[byte_pos] = intermediate[byte_pos] ^ prev_block[byte_pos]
break
plaintext += bytes(decrypted)
return plaintext
1.4 Tools
# PadBuster
padbuster http://target/decrypt?ct= CIPHERTEXT_HEX 16 -encoding 0
padbuster http://target/decrypt?ct= CIPHERTEXT_HEX 16 -encoding 0 -plaintext "admin=true"
2. CBC BIT FLIPPING
2.1 Concept
Flipping bit at position j in C_{i-1} flips the same bit at position j in P_i (and corrupts all of P_{i-1}).
Original: P_i[j] = D_K(C_i)[j] ⊕ C_{i-1}[j]
Modified: P'_i[j] = D_K(C_i)[j] ⊕ C'_{i-1}[j]
= P_i[j] ⊕ (C_{i-1}[j] ⊕ C'_{i-1}[j])
2.2 Practical Example
def cbc_bitflip(ciphertext, block_size, target_byte_pos, old_value, new_value):
"""
Flip byte in plaintext block N+1 by modifying ciphertext block N.
target_byte_pos: absolute position in plaintext (0-indexed)
"""
ct = bytearray(ciphertext)
block_num = target_byte_pos // block_size
byte_in_block = target_byte_pos % block_size
# Modify previous block (block_num - 1) to flip target byte
modify_pos = (block_num - 1) * block_size + byte_in_block
# XOR to cancel old value and set new value
ct[modify_pos] ^= old_value ^ new_value
return bytes(ct)
# Example: flip "admin=0" to "admin=1"
# If "admin=0" is at byte position 22 (block 1, byte 6):
modified_ct = cbc_bitflip(ciphertext, 16, 22, ord('0'), ord('1'))
3. ECB MODE ATTACKS
3.1 Detection
def detect_ecb(ciphertext, block_size=16):
"""ECB produces identical blocks for identical plaintext blocks."""
blocks = [ciphertext[i:i+block_size] for i in range(0, len(ciphertext), block_size)]
return len(blocks) != len(set(blocks))
# Force detection: send repeated plaintext
test_input = b"A" * 48 # at least 3 blocks of identical data
# If response has repeated blocks → ECB
3.2 ECB Cut-and-Paste
Reorder ciphertext blocks to create new valid plaintexts.
Original blocks:
Block 0: "email=foo@bar.c"
Block 1: "om&role=user&uid"
Block 2: "=10\x0d\x0d\x0d..."
Attack: craft input so "admin" + padding lands in its own block,
then swap it in place of "user" block.
Step 1: Send email that aligns "admin" + PKCS7 to a block:
email = "foo@bar.coadmin\x0b\x0b\x0b\x0b\x0b\x0b\x0b\x0b\x0b\x0b\x0b"
→ Block 1 encrypts "admin\x0b\x0b..." (save this block)
Step 2: Send email that puts "role=" at end of block:
email = "foo@bar.co"
→ Block 2 = "=user&uid=10..." (but we replace this)
Step 3: Replace last block with saved "admin\x0b..." block
3.3 Byte-at-a-Time ECB Decryption
Decrypt unknown appended secret one byte at a time.
def ecb_byte_at_a_time(encrypt_oracle, block_size=16):
"""
encrypt_oracle(input_bytes) = AES_ECB(input || unknown_secret)
Returns the unknown_secret.
"""
secret = b""
secret_len = len(encrypt_oracle(b""))
for i in range(secret_len):
block_num = i // block_size
pad_len = block_size - 1 - (i % block_size)
padding = b"A" * pad_len
# Build lookup table
target_ct = encrypt_oracle(padding)
target_block = target_ct[block_num * block_size:(block_num + 1) * block_size]
for byte_val in range(256):
test_input = padding + secret + bytes([byte_val])
test_ct = encrypt_oracle(test_input)
test_block = test_ct[block_num * block_size:(block_num + 1) * block_size]
if test_block == target_block:
secret += bytes([byte_val])
break
return secret
4. STREAM CIPHER ATTACKS
4.1 Known Plaintext / Key Reuse (Two-Time Pad)
def two_time_pad(c1, c2, known_crib=None):
"""
c1 = m1 ⊕ K, c2 = m2 ⊕ K (same key K)
c1 ⊕ c2 = m1 ⊕ m2 (key cancels)
"""
xored = bytes(a ^ b for a, b in zip(c1, c2))
if known_crib:
results = []
for offset in range(len(xored) - len(known_crib) + 1):
candidate = bytes(
xored[offset + i] ^ known_crib[i] for i in range(len(known_crib))
)
if all(0x20 <= b <= 0x7e for b in candidate):
results.append((offset, candidate))
return results
return xored
4.2 Single-Byte XOR Brute Force
def single_byte_xor_crack(ciphertext):
"""Brute force single-byte XOR key using frequency analysis."""
english_freq = {
'e': 12.7, 't': 9.1, 'a': 8.2, 'o': 7.5, 'i': 7.0,
'n': 6.7, 's': 6.3, 'h': 6.1, 'r': 6.0, 'd': 4.3,
}
best_score, best_key, best_plaintext = 0, 0, b""
for key in range(256):
plaintext = bytes(b ^ key for b in ciphertext)
score = sum(
english_freq.get(chr(b).lower(), 0)
for b in plaintext if 0x20 <= b <= 0x7e
)
if score > best_score:
best_score = score
best_key = key
best_plaintext = plaintext
return best_key, best_plaintext
4.3 Repeating-Key XOR (Kasiski-like)
def repeating_xor_crack(ciphertext, max_keylen=40):
"""Crack repeating-key XOR using Hamming distance for key length."""
def hamming(a, b):
return sum(bin(x ^ y).count('1') for x, y in zip(a, b))
# Find key length
scores = []
for kl in range(2, max_keylen + 1):
blocks = [ciphertext[i:i+kl] for i in range(0, len(ciphertext) - kl, kl)]
if len(blocks) < 4:
continue
dist = sum(hamming(blocks[i], blocks[i+1]) for i in range(min(3, len(blocks)-1)))
normalized = dist / (min(3, len(blocks)-1) * kl)
scores.append((normalized, kl))
best_keylen = sorted(scores)[0][1]
# Crack each position with single-byte XOR
key = b""
for i in range(best_keylen):
column = bytes(ciphertext[j] for j in range(i, len(ciphertext), best_keylen))
k, _ = single_byte_xor_crack(column)
key += bytes([k])
return key
4.4 LFSR State Recovery (Berlekamp-Massey)
def berlekamp_massey_gf2(output_bits):
"""Recover LFSR feedback polynomial from output sequence over GF(2)."""
n = len(output_bits)
C = [0] * (n + 1)
B = [0] * (n + 1)
C[0] = B[0] = 1
L = 0
m = 1
b = 1
for N in range(n):
d = output_bits[N]
for i in range(1, L + 1):
d ^= C[i] & output_bits[N - i]
if d == 0:
m += 1
elif 2 * L <= N:
T = C[:]
for i in range(m, n + 1):
C[i] ^= B[i - m]
L = N + 1 - L
B = T
b = d
m = 1
else:
for i in range(m, n + 1):
C[i] ^= B[i - m]
m += 1
return C[:L + 1], L
4.5 RC4 Biases
| Bias | Description | Exploitation |
|---|---|---|
| Initial byte bias | P(K[0] = 0) ≈ 2/256 (double normal) | Statistical plaintext recovery for first bytes |
| Fluhrer-Mantin-Shamir | Weak key scheduling with IV | WEP attack (historical) |
| NOMORE attack | Long-term biases in keystream | TLS/RC4 plaintext recovery (2^24-2^26 ciphertexts) |
| Invariance weakness | Key-dependent biases throughout stream | Statistical attack on many encryptions |
5. MEET-IN-THE-MIDDLE
5.1 Double Encryption Attack
Double encryption: C = E_K2(E_K1(P))
Brute force: 2^(2n) expected
MITM: 2^(n+1) + storage for 2^n entries
Attack:
1. Encrypt P with all possible K1 → store (E_K1(P), K1) in table
2. Decrypt C with all possible K2 → check if D_K2(C) matches any entry
3. Match found → (K1, K2) recovered
from itertools import product
def meet_in_the_middle(encrypt, decrypt, plaintext, ciphertext, keyspace_bits):
"""MITM attack on double encryption."""
# Phase 1: build encryption table
enc_table = {}
for k1 in range(2**keyspace_bits):
intermediate = encrypt(plaintext, k1)
enc_table[intermediate] = k1
# Phase 2: decrypt and look up
for k2 in range(2**keyspace_bits):
intermediate = decrypt(ciphertext, k2)
if intermediate in enc_table:
k1 = enc_table[intermediate]
return k1, k2
return None
6. DECISION TREE
Symmetric cipher challenge — what can you observe?
│
├─ Can you detect the mode?
│ ├─ Repeated input → repeated output blocks?
│ │ └─ Yes → ECB mode
│ │ ├─ Can control prefix → byte-at-a-time decryption
│ │ ├─ Can reorder blocks → cut-and-paste
│ │ └─ Can detect block boundaries → block alignment oracle
│ │
│ ├─ Error message differs for bad padding?
│ │ └─ Yes → Padding oracle (CBC)
│ │ └─ PadBuster or custom script
│ │
│ └─ Can modify ciphertext and observe effect?
│ └─ Next-block plaintext changes → CBC bit flipping
│
├─ Stream cipher or XOR?
│ ├─ Key reused on different messages?
│ │ └─ XOR ciphertexts → crib drag
│ │
│ ├─ Known plaintext-ciphertext pair?
│ │ └─ Recover keystream directly
│ │
│ ├─ Single-byte XOR key?
│ │ └─ Brute force 256 keys with frequency analysis
│ │
│ ├─ Repeating-key XOR?
│ │ └─ Hamming distance → key length → per-position crack
│ │
│ └─ LFSR-based?
│ └─ Berlekamp-Massey for state/polynomial recovery
│
├─ PRNG-based cipher?
│ ├─ LCG → truncated output lattice attack
│ ├─ Mersenne Twister → 624 outputs → full state recovery
│ └─ Custom PRNG → analyze period and state size
│
├─ Double / triple encryption?
│ └─ Meet-in-the-middle
│
└─ RC4 specifically?
├─ Single encryption → initial byte bias
├─ Many encryptions same key → statistical attack
└─ IV prepended to key → FMS attack (WEP-like)
7. TOOLS
| Tool | Purpose |
|---|---|
| PadBuster | Automated padding oracle exploitation |
| xortool | Repeating-key XOR analysis (key length detection + cracking) |
| CyberChef | Quick XOR, encoding, block cipher operations |
| SageMath | LFSR/LCG analysis, lattice-based recovery |
| pycryptodome | AES/DES implementation for testing |
| hashcat | Brute force symmetric keys (GPU-accelerated) |
| Custom Python | All attacks above implementable in pure Python |
FAQ
What does the symmetric-cipher-attacks skill do?
Symmetric cipher attack playbook. Use when exploiting block cipher mode weaknesses (CBC padding oracle, ECB cut-and-paste, bit flipping), stream cipher key reuse, or meet-in-the-middle attacks.
How do I install symmetric-cipher-attacks?
Run npx skills add https://github.com/yaklang/hack-skills --skill symmetric-cipher-attacks in your project. The skills CLI detects the agents you use and copies the skill into the right folder. For Claude Code you can also place the skill folder at ~/.claude/skills/symmetric-cipher-attacks/ (personal) or .claude/skills/symmetric-cipher-attacks/ (project).
Which AI agents can use symmetric-cipher-attacks?
Any agent that supports the open Agent Skills format (a folder with a SKILL.md file), including Claude Code, Codex, Cursor, GitHub Copilot, Gemini CLI, Windsurf, Cline, OpenCode and more.
Is symmetric-cipher-attacks safe to install?
No partner security audit is available yet. Skills can run commands and scripts, so read the SKILL.md and any bundled files before installing.
Who maintains symmetric-cipher-attacks?
It is published by yaklang in yaklang/hack-skills. It has 3,536 recorded installs.
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