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Anthropic·Software Engineer·Onsite - System Design / Architecture·Senior

SeniorPrefer not to say
May 2026

Summary

System design round at Anthropic for a software engineering role, centered entirely on building a duplicate file finder from scratch. Pretty deep dive, they wanted to talk through everything from OS primitives to complexity analysis.

Questions Asked (5)

Q1

Design a command-line tool that finds duplicate files in a directory tree. Walk through how you'd enumerate files, filter candidates, and confirm duplicates efficiently.

System DesignAlgorithms & Data StructuresTechnical Trade-offs
Author's notes

I started with the naive approach (hash everything) and they immediately pushed back on memory.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements (e.g., file types, symlinks, performance constraints) and then walk through a multi-stage pipeline: enumerate files, group by size, hash candidates, and compare hashes. Emphasize efficiency by using size as a cheap filter and hashing only when necessary, and discuss trade-offs like hashing algorithm choice and memory usage.

Pro tip: Mention that you can use a two-level hashing approach: first hash a small portion of the file (e.g., first 4KB) to quickly eliminate non-duplicates, then hash the full file only for those that match. This shows practical optimization skills.

1. Clarify Requirements and Constraints

Ask about expected directory size, file types, symlink handling, and performance requirements. This ensures the design meets the actual needs.

2. Enumerate Files Efficiently

Use a recursive directory walk (e.g., os.walk in Python) to list all files, skipping directories or symlinks as needed. Consider using a generator to avoid loading all paths into memory.

3. Group by File Size

Group files by their size; files with unique sizes cannot be duplicates. This cheap filter drastically reduces the number of files to compare.

4. Hash and Compare Candidates

For each size group with more than one file, compute a hash (e.g., SHA-256) of the file contents. Group files by hash to identify duplicates. Optionally, use a partial hash first to reduce I/O.

5. Report and Handle Edge Cases

Output duplicate groups, and discuss handling of empty files, hard links, and permission errors. Mention potential optimizations like parallel hashing.

Key Points to Mention

  • Use file size as a cheap first-pass filter to avoid unnecessary hashing.
  • Choose a cryptographic hash (e.g., SHA-256) for low collision probability, or a faster non-cryptographic hash (e.g., xxHash) if collisions are acceptable.
  • Consider memory usage: avoid storing all file contents; process files in a streaming fashion.
  • Handle edge cases: empty files, symlinks, hard links, and files that change during the scan.
  • Discuss trade-offs: time vs. space, hashing algorithm speed vs. collision resistance, and single-threaded vs. parallel processing.
  • Mention that the tool should be robust: handle permission errors gracefully and provide clear output.

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

Q2

What are the memory and I/O trade-offs when handling very large files in this tool?

Technical Trade-offsSystem Design
Author's notes

They kept pulling on this thread.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the tool's context and the scale of 'very large' files, then systematically compare in-memory vs. streaming approaches across memory usage, I/O patterns, and performance. Conclude with a recommendation that balances trade-offs based on the tool's constraints and use cases.

Pro tip: Demonstrate awareness that the optimal solution often involves a hybrid approach, such as memory-mapping for random access or chunked processing with backpressure, and mention how you'd measure and validate the trade-offs with benchmarks.

1. Clarify requirements and constraints

Ask about file size ranges, access patterns (sequential vs. random), latency/throughput needs, and available memory. This ensures your answer is tailored to the actual problem.

2. Analyze memory trade-offs

Compare loading entire file into memory (fast but high memory, risk of OOM) vs. streaming/chunking (low memory but more complex, potential overhead). Mention memory-mapped files as a middle ground.

3. Analyze I/O trade-offs

Discuss sequential vs. random I/O, buffering strategies, and the impact of disk vs. network I/O. Highlight how chunk size affects throughput and latency.

4. Evaluate performance and scalability

Consider CPU overhead, parallelism, and how the approach scales with file size and concurrent users. Mention profiling and benchmarking to validate choices.

5. Recommend a balanced solution

Propose a hybrid or adaptive strategy (e.g., streaming with configurable buffer, memory-mapping for random access) and explain how it addresses the trade-offs for this tool.

Key Points to Mention

  • In-memory processing: fast but memory-bound; risk of OutOfMemory errors for very large files.
  • Streaming/chunked processing: constant memory usage but may increase I/O operations and complexity.
  • Memory-mapped files: leverage OS page cache, good for random access, but can cause page faults and unpredictable performance.
  • I/O patterns: sequential vs. random access, buffering, and the impact of read/write sizes on throughput.
  • Backpressure and flow control: essential when streaming to avoid overwhelming consumers or producers.
  • Benchmarking and profiling: measure memory footprint, throughput, and latency to make data-driven decisions.

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

Q3

How would you handle symlinks and permission errors when recursively walking the directory tree?

System DesignTechnical Trade-offs
Author's notes

Blanked for a second.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements: what should happen when a symlink is encountered (follow, skip, or detect cycles) and how to handle permission errors (fail fast, log and continue, or collect and report). Then describe a robust implementation using os.walk with followlinks=False, onerror callback, and cycle detection via visited inodes, and discuss trade-offs between resilience and correctness.

Pro tip: Mention that you would make the behavior configurable (e.g., follow_symlinks flag, error handling policy) because different use cases demand different trade-offs, and that you'd log errors with enough context to debug without crashing the entire walk.

1. Clarify requirements and constraints

Ask whether symlinks should be followed, how to handle cycles, and whether permission errors should abort or be collected. Also consider performance and security implications.

2. Choose the right traversal API

Use os.walk with followlinks=False by default, and provide an onerror callback to handle permission errors gracefully. For more control, consider os.scandir for manual recursion.

3. Implement symlink handling and cycle detection

If following symlinks, track visited (device, inode) pairs to avoid infinite loops. Use os.path.realpath or os.stat with follow_symlinks=False to detect symlinks.

4. Handle permission errors robustly

Catch PermissionError in the onerror callback, log the path and error, and decide whether to continue or abort based on policy. Optionally collect errors for later reporting.

5. Discuss trade-offs and edge cases

Explain the trade-offs between following symlinks (convenience vs. cycles/security) and error handling (resilience vs. silent failures). Mention edge cases like broken symlinks, special files, and network filesystems.

Key Points to Mention

  • Use os.walk with followlinks=False by default to avoid symlink cycles.
  • Implement cycle detection with a set of visited (st_dev, st_ino) pairs when following symlinks.
  • Provide an onerror callback to os.walk to handle PermissionError and other OSErrors without crashing.
  • Consider using os.scandir for more efficient and fine-grained control over traversal.
  • Log errors with full path and error details, and make error handling policy configurable.
  • Be aware of security risks like symlink attacks and TOCTOU issues when following symlinks.

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

Q4

Once you've identified groups of duplicate files, what options would you expose to the user for resolving them, and what are the risks of each?

System DesignAPI & Integrations
Author's notes

Hard-link, move, delete.

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AI HintsAI Generated

Suggested Approach

Start by framing the problem: duplicate resolution is a destructive operation, so the design must prioritize safety and user control. Then enumerate resolution options from least to most destructive, explaining the risks and mitigations for each. Finally, tie it back to system design principles like idempotency, auditability, and user experience.

Pro tip: Emphasize that the safest default is to never auto-delete; instead, offer reversible actions like quarantine or hard-linking, and always provide a dry-run preview. This shows you think about real-world failure modes and user trust.

1. Clarify the goal and constraints

Restate the problem: the user wants to reclaim space or organize files without losing important data. Mention constraints like irreversibility, performance, and cross-platform differences.

2. Enumerate resolution options

List options such as: keep one copy and delete others, move duplicates to a quarantine folder, replace duplicates with hard links or symlinks, merge metadata, or do nothing. Order them from safest to most destructive.

3. Analyze risks and mitigations for each option

For each option, describe the risk (e.g., accidental deletion of unique data, broken links, permission issues) and propose mitigations (e.g., dry-run, undo, backup, confirmation dialogs).

4. Recommend a safe default and user experience

Suggest a default action that is reversible and transparent, such as moving to a quarantine folder with a retention period. Explain how to present choices to the user with clear warnings.

5. Connect to system design principles

Tie the discussion to broader engineering concerns: idempotency, audit logging, concurrency, and API design for exposing these options programmatically.

Key Points to Mention

  • Reversibility and undo mechanisms (e.g., quarantine, trash, versioning)
  • Hard links vs. symlinks vs. copies: trade-offs in space, portability, and risk
  • Dry-run and preview capabilities to avoid accidental data loss
  • User confirmation and clear warnings for destructive actions
  • Audit logging and idempotency for API-driven operations
  • Cross-platform filesystem differences (e.g., NTFS vs. APFS vs. ext4) affecting link support and permissions

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

Q5

What is the time and space complexity of your duplicate detection approach?

Algorithms & Data Structures
Author's notes

Standard closer.

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AI HintsAI Generated

Suggested Approach

Start by clearly stating the time and space complexity of your duplicate detection approach, using Big-O notation. Then, briefly explain how you arrived at these complexities by walking through the algorithm's steps and the data structures used. Finally, discuss any trade-offs between time and space and mention possible optimizations or alternative approaches.

Pro tip: Always relate the complexity to the specific constraints of the problem, such as input size or memory limits, and mention if your solution is optimal or if there's room for improvement. This shows you consider practical engineering trade-offs, not just theoretical analysis.

1. State the complexities

Clearly state the time and space complexity of your approach in Big-O notation, e.g., O(n) time and O(n) space.

2. Explain the reasoning

Walk through the algorithm step by step, identifying the dominant operations and how they scale with input size. Mention the data structures used and their impact on complexity.

3. Discuss trade-offs

Explain any trade-offs between time and space, such as using extra space to achieve faster time, and whether this is acceptable given typical constraints.

4. Mention alternatives

Briefly describe alternative approaches and their complexities, highlighting why you chose your approach.

5. Conclude with optimization

If applicable, mention potential optimizations or edge cases that could affect complexity, showing depth of analysis.

Key Points to Mention

  • Time complexity analysis (e.g., O(n) for hash set approach)
  • Space complexity analysis (e.g., O(n) for storing seen elements)
  • Data structures used (e.g., hash set, sorting) and their impact
  • Trade-offs between time and space (e.g., sorting in-place vs. using extra memory)
  • Edge cases (e.g., empty input, all duplicates) and their effect on complexity
  • Comparison with alternative approaches (e.g., brute force O(n^2), sorting O(n log n))

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