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Cursor·Software Engineer·Technical Phone Screen·Senior

SeniorPrefer not to say
Apr 2026Remote

Summary

Cursor SE interview that went deep on cryptographic data structures. The whole session was basically one long Merkle tree implementation with a lot of follow-up questions baked in. Not a bad experience but I underestimated how much they'd push on the security angles.

Questions Asked (4)

Q1

Implement a Merkle tree from scratch given a list of data blocks. You need to support building the tree, returning the root hash, generating an inclusion proof for a leaf at a given index, and verifying that proof.

Algorithms & Data StructuresSystem Design
Author's notes

I started with the build function and got through it okay, hashing leaves then pairwise hashing up.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and edge cases, then design the Merkle tree structure with a clear hashing scheme. Implement the core operations—build, get root, generate proof, and verify—using a bottom-up approach, and test with small examples to ensure correctness.

Pro tip: Mention that you would use a domain separation prefix (e.g., 0x00 for leaves, 0x01 for internal nodes) to prevent second preimage attacks, and discuss how to handle odd numbers of nodes by duplicating the last node or promoting it.

1. Clarify requirements and edge cases

Ask about the hash function (e.g., SHA-256), handling of empty input, odd number of leaves, and whether the tree should be balanced. Confirm the proof format and verification process.

2. Design the tree structure and hashing scheme

Define a node as either a leaf (hash of data with a prefix) or an internal node (hash of concatenated child hashes with a prefix). Decide on a bottom-up construction, possibly using a list of levels.

3. Implement build and root hash

Build the tree level by level: hash each data block to create leaves, then repeatedly pair and hash nodes until a single root remains. Return the root hash.

4. Implement proof generation and verification

For a given leaf index, traverse the tree from leaf to root, collecting sibling hashes and their positions (left/right). To verify, recompute hashes up the tree using the proof and compare with the root.

5. Test and discuss optimizations

Test with edge cases (empty, single leaf, odd leaves) and verify proofs. Discuss potential optimizations like caching levels or using a compact representation.

Key Points to Mention

  • Hash function choice and domain separation to prevent second preimage attacks
  • Handling odd number of leaves (duplicating last node or promoting)
  • Proof format: list of sibling hashes and direction (left/right)
  • Verification algorithm: recompute root from leaf and proof
  • Time and space complexity: O(n) build, O(log n) proof generation and verification
  • Edge cases: empty input, single leaf, invalid proof

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q2

How do you handle an odd number of leaves when building the Merkle tree?

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

Said duplicate the last leaf, which is the standard approach.

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AI HintsAI Generated

Suggested Approach

Start by explaining the standard approach of duplicating the last leaf (or promoting it) to make the number of nodes even at each level, then discuss the trade-offs and alternatives like carrying the odd node up. Emphasize that the choice affects tree shape, proof size, and security, and mention how real-world systems like Bitcoin handle it.

Pro tip: Mention that duplicating the last leaf can create a CVE-like vulnerability (e.g., Bitcoin's CVE-2012-2459) where two different leaf sets produce the same root, so some implementations use domain separation or promote the odd node instead.

1. Identify the problem

Explain that Merkle trees require pairs of nodes to hash together, so an odd number of leaves at any level leaves one node without a sibling.

2. Present common solutions

Describe the two main approaches: duplicating the last node (Bitcoin-style) or promoting the odd node to the next level unchanged.

3. Analyze trade-offs

Compare the solutions in terms of proof size, tree shape, security implications (e.g., second preimage attacks), and implementation complexity.

4. Discuss real-world usage

Mention how specific systems (e.g., Bitcoin, Ethereum, Certificate Transparency) handle odd leaves and any known vulnerabilities or fixes.

5. Recommend a robust approach

Suggest best practices such as using domain separation, avoiding duplication, or using a balanced tree structure to mitigate risks.

Key Points to Mention

  • Duplicating the last leaf is common but can lead to second preimage attacks if not carefully implemented.
  • Promoting the odd node avoids duplication but changes the tree's balance and proof paths.
  • Bitcoin duplicates the last hash and has a known vulnerability (CVE-2012-2459) related to this.
  • Domain separation (e.g., prefixing leaf vs. internal nodes) can prevent ambiguity.
  • Proof size and verification efficiency depend on the chosen method.
  • Some implementations use a balanced tree by padding with a special value or using a different structure.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q3

What hash function would you choose and how would you protect against second-preimage attacks in a Merkle tree?

Technical Trade-offsSystem Design
Author's notes

SHA-256 was easy.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and threat model, then recommend a modern hash function like SHA-256 or BLAKE3, explaining why it resists second-preimage attacks. Describe how to structure the Merkle tree (e.g., domain separation, leaf vs. internal node prefixes) and mention additional protections like length extension defenses and canonical ordering.

Pro tip: Mention that using a hash function with a large output size (e.g., 256 bits) and proper domain separation is crucial; also note that for performance-critical applications, BLAKE3 offers built-in tree hashing and is resistant to length extension attacks.

1. Clarify requirements and threat model

Ask about the use case, performance constraints, and security requirements (e.g., collision resistance, second-preimage resistance). Determine if the tree is used for integrity verification, blockchain, or file systems.

2. Choose a hash function

Recommend a cryptographically secure hash function like SHA-256 or BLAKE3. Explain that SHA-256 is widely standardized and secure, while BLAKE3 is faster and designed for tree hashing.

3. Explain second-preimage resistance

Define second-preimage resistance: given a message and its hash, it's infeasible to find a different message with the same hash. Note that Merkle trees require this property for both leaves and internal nodes.

4. Describe Merkle tree construction with domain separation

Use distinct prefixes for leaf and internal nodes (e.g., 0x00 for leaves, 0x01 for internal) to prevent second-preimage attacks where an internal node hash could be mistaken for a leaf hash. Also, ensure that the tree is built deterministically (e.g., sorted leaves if needed).

5. Mention additional protections

Include length extension defenses (e.g., use HMAC or a hash function not vulnerable to length extension), and consider using a Merkle tree variant like a Merkle Patricia Trie for key-value stores. Also, discuss the importance of using a secure padding scheme.

Key Points to Mention

  • Second-preimage resistance vs. collision resistance
  • Domain separation (leaf vs. internal node prefixes)
  • Choice of hash function: SHA-256, SHA-3, BLAKE3
  • Length extension attacks and how to mitigate them
  • Deterministic tree construction and canonical ordering
  • Performance and security trade-offs (e.g., BLAKE3 for speed)

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.

Q4

What is the time and space complexity for building the tree, generating a proof, and verifying a proof?

Algorithms & Data Structures
Author's notes

Build is O(n), proof and verify are both O(log n).

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AI HintsAI Generated

Suggested Approach

Clarify the specific tree structure (e.g., Merkle tree) and the proof system (e.g., Merkle proof) before diving into complexities. Then systematically analyze each phase—building, proving, verifying—by considering the number of nodes, proof size, and computational steps, and express complexities in terms of the number of leaves (n) and possibly tree height (h).

Pro tip: Always state your assumptions about the tree's branching factor and whether it's balanced; for example, a binary Merkle tree has height log n, which directly impacts proof size and verification time. This shows you understand the practical implications and can adapt to different scenarios.

1. Clarify the data structure and operations

Confirm that the question refers to a Merkle tree (or similar) and define the operations: building the tree from n leaves, generating a proof for a specific leaf, and verifying that proof. Ask if the tree is binary and balanced.

2. Analyze tree construction complexity

Building the tree requires hashing each leaf and then hashing pairs up the tree. For n leaves, there are about 2n nodes, so time is O(n) and space is O(n) to store the tree.

3. Analyze proof generation complexity

A proof consists of sibling hashes along the path from leaf to root. For a balanced binary tree, the path length is O(log n), so generating the proof takes O(log n) time and space (to store the proof).

4. Analyze proof verification complexity

Verification involves recomputing hashes along the path using the proof. This takes O(log n) time and O(1) additional space (beyond the proof itself), as you only need to store the current hash and the proof elements.

5. Summarize and discuss trade-offs

State the complexities clearly: build O(n) time/space, prove O(log n) time/space, verify O(log n) time/O(1) space. Mention that these hold for balanced binary trees; unbalanced trees could degrade to O(n) in the worst case.

Key Points to Mention

  • Merkle tree construction: O(n) time and space due to hashing all nodes.
  • Proof size and generation: O(log n) for balanced binary trees, as it includes sibling hashes along the path.
  • Verification time: O(log n) hashing operations, independent of tree size beyond height.
  • Verification space: O(1) extra space if proof is given, or O(log n) if counting proof storage.
  • Impact of tree balance: worst-case O(n) for skewed trees, so balanced trees are preferred.
  • Assumptions: binary tree, cryptographic hash function with O(1) time per hash.

AI-generated suggestions, not part of the candidate's original notes. May be inaccurate — verify before relying on them.