Key-length extension (KLE) techniques provide a general approach to enhancing the security of block ciphers by using longer keys. There are mainly two classes of KLE techniques, cascade encryption and XOR-cascade encryption. This paper presents several quantum meet-in-the-middle (MITM) attacks against two specific KLE constructions. For the two-key triple encryption (2kTE), we propose two quantum MITM attacks under the Q2 model. The first attack, leveraging the quantum claw-finding (QCF) algorithm, achieves a time complexity of $O(2^{2κ/3})$ with $O(2^{2κ/3})$ quantum random access memory (QRAM). The second attack, based on Grover's algorithm, achieves a time complexity of $O(2^{κ/2})$ with $O(2^κ)$ QRAM. The latter complexity is nearly identical to Grover-based brute-force attack on the underlying block cipher, indicating that 2kTE does not enhance security under the Q2 model when sufficient QRAM resources are available. For the 3XOR-cascade encryption (3XCE), we propose a quantum MITM attack applicable to the Q1 model. This attack requires no QRAM and has a time complexity of $O(2^{(κ+n)/2})$ ( $κ$ and $n$ are the key length and block length of the underlying block cipher, respectively.), achieving a quadratic speedup over classical MITM attack. Furthermore, we extend the quantum MITM attack to quantum sieve-in-the-middle (SITM) attack, which is applicable for more constructions. We present a general quantum SITM framework for the construction $ELE=E^2\circ L\circ E^1$ and provide specific attack schemes for three different forms of the middle layer $L$ . The quantum SITM attack technique can be further applied to a broader range of quantum cryptanalysis scenarios.Key-length extension (KLE) techniques provide a general approach to enhancing the security of block ciphers by using longer keys. There are mainly two classes of KLE techniques, cascade encryption and XOR-cascade encryption. This paper presents several quantum meet-in-the-middle (MITM) attacks against two specific KLE constructions. For the two-key triple encryption (2kTE), we propose two quantum MITM attacks under the Q2 model. The first attack, leveraging the quantum claw-finding (QCF) algorithm, achieves a time complexity of $O(2^{2κ/3})$ with $O(2^{2κ/3})$ quantum random access memory (QRAM). The second attack, based on Grover's algorithm, achieves a time complexity of $O(2^{κ/2})$ with $O(2^κ)$ QRAM. The latter complexity is nearly identical to Grover-based brute-force attack on the underlying block cipher, indicating that 2kTE does not enhance security under the Q2 model when sufficient QRAM resources are available. For the 3XOR-cascade encryption (3XCE), we propose a quantum MITM attack applicable to the Q1 model. This attack requires no QRAM and has a time complexity of $O(2^{(κ+n)/2})$ ($κ$ and $n$ are the key length and block length of the underlying block cipher, respectively.), achieving a quadratic speedup over classical MITM attack. Furthermore, we extend the quantum MITM attack to quantum sieve-in-the-middle (SITM) attack, which is applicable for more constructions. We present a general quantum SITM framework for the construction $ELE=E^2\circ L\circ E^1$ and provide specific attack schemes for three different forms of the middle layer $L$. The quantum SITM attack technique can be further applied to a broader range of quantum cryptanalysis scenarios.

cs.CRCross-listedarXiv:2511.09351Quantum Information ProcessingNov 13, 20250 citations

A Quantum Circuit to Execute a Key-Recovery Attack Against the DES and 3DES Block Ciphers

Simone Perriello, Alessandro Barenghi, Gerardo Pelosi

Quantum computing enabled cryptanalytic techniques are able to concretely reduce the security margin of existing cryptographic primitives. While this reduction is only polynomial for symmetric cryptosystems, it still provides a reduction in their security margin. In this work, we propose a detailed quantum circuit designed to cryptanalyze both the Data Encryption Standard (DES) cryptosystem, and its successor Triple-DES (3DES), currently standardized in ISO/IEC 18033–3, and still widely employed in satellite data and bank card encryption. To do so, we introduce the first quantum circuit implementation of the 8 substitution tables (a.k.a. S-boxes), applying a bitslicing strategy, which is currently the most efficient classical combinatorial circuit design in terms of number of two inputs Boolean gates. Secondly, we present the complete quantum circuits required to attack both DES and 3DES leveraging Grover's algorithm. We provide finite regime, closed form equations, delineating the circuits complexities in terms of the number of qubits, gates, depth and number of qubits multiplied by depth. The complexity analysis is based on two distinct gate sets: a NOT-CNOT-Toffoli (NCT) extended with the Hadamard gate; and the fault-tolerant Clifford+T. Finally, akin to the classical attack to the 3DES, we introduce a meet-in-the-middle strategy relying on an exponential amount of Quantum Random Access Memory. Our findings show that the 3DES with keying option 2, the most widely employed variant of 3DES, can be attacked with a circuit depth of approximately $2^{67}$ and less than a thousand qubits. This is close to the $2^{64}$ value suggested by NIST for the depth achievable sequentially by a single quantum computer in a decade. Our technique can be further sped up parallelizing the approach onto multiple devices, pointing to the practicality of cryptanalyzing 3DES in such a scenario.Quantum computing enabled cryptanalytic techniques are able to concretely reduce the security margin of existing cryptographic primitives. While this reduction is only polynomial for symmetric cryptosystems, it still provides a reduction in their security margin. In this work, we propose a detailed quantum circuit designed to cryptanalyze both the Data Encryption Standard (DES) cryptosystem, and its successor Triple-DES (3DES), currently standardized in ISO/IEC 18033–3, and still widely employed in satellite data and bank card encryption. To do so, we introduce the first quantum circuit implementation of the 8 substitution tables (a.k.a. S-boxes), applying a bitslicing strategy, which is currently the most efficient classical combinatorial circuit design in terms of number of two inputs Boolean gates. Secondly, we present the complete quantum circuits required to attack both DES and 3DES leveraging Grover's algorithm. We provide finite regime, closed form equations, delineating the circuits complexities in terms of the number of qubits, gates, depth and number of qubits multiplied by depth. The complexity analysis is based on two distinct gate sets: a NOT-CNOT-Toffoli (NCT) extended with the Hadamard gate; and the fault-tolerant Clifford+T. Finally, akin to the classical attack to the 3DES, we introduce a meet-in-the-middle strategy relying on an exponential amount of Quantum Random Access Memory. Our findings show that the 3DES with keying option 2, the most widely employed variant of 3DES, can be attacked with a circuit depth of approximately$2^{67}$and less than a thousand qubits. This is close to the$2^{64}$value suggested by NIST for the depth achievable sequentially by a single quantum computer in a decade. Our technique can be further sped up parallelizing the approach onto multiple devices, pointing to the practicality of cryptanalyzing 3DES in such a scenario.

IEEE International Conference on Quantum Computing and Engineering (QCE)Sep 15, 20241 citation

O(2^{2κ/3})

with

O(2^{2κ/3})

quantum random access memory (QRAM). The second attack, based on Grover's algorithm, achieves a time complexity of

O(2^{κ/2})

with

O(2^κ)

QRAM. The latter complexity is nearly identical to Grover-based brute-force attack on the underlying block cipher, indicating that 2kTE does not enhance security under the Q2 model when sufficient QRAM resources are available. For the 3XOR-cascade encryption (3XCE), we propose a quantum MITM attack applicable to the Q1 model. This attack requires no QRAM and has a time complexity of

O(2^{(κ+n)/2})

(

κ

and

n

are the key length and block length of the underlying block cipher, respectively.), achieving a quadratic speedup over classical MITM attack. Furthermore, we extend the quantum MITM attack to quantum sieve-in-the-middle (SITM) attack, which is applicable for more constructions. We present a general quantum SITM framework for the construction

ELE=E^2\circ L\circ E^1

and provide specific attack schemes for three different forms of the middle layer

L

. The quantum SITM attack technique can be further applied to a broader range of quantum cryptanalysis scenarios.

2^{67}

and less than a thousand qubits. This is close to the

2^{64}

value suggested by NIST for the depth achievable sequentially by a single quantum computer in a decade. Our technique can be further sped up parallelizing the approach onto multiple devices, pointing to the practicality of cryptanalyzing 3DES in such a scenario.