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Anthropic·Software Engineer·Technical Phone Screen·Senior

SeniorPrefer not to say
Jun 2026Remote

Summary

Anthropic software engineer interview with a systems-flavored coding problem. The main question was a file deduplication tool, followed by a pretty deep follow-up discussion on scaling and parallelism. Nothing behavioral, just technical the whole way through.

Questions Asked (5)

Q1

Implement a file deduplication tool that recursively scans a directory, groups files by size, uses content hashing to find duplicates, and returns only groups with at least two matching files. Must handle large files without loading them fully into memory and deal gracefully with permission errors or files changing mid-scan.

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

This one took me a minute to get into the right headspace.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements and constraints, then outline a multi-pass algorithm: first collect file metadata (size, path) while handling errors, then group by size, and finally hash only files within size groups using streaming to avoid memory issues. Discuss trade-offs like hash choice, concurrency, and handling files that change mid-scan, and consider edge cases like empty files and symlinks.

Pro tip: Mention that you would use a fast non-cryptographic hash (e.g., xxHash or BLAKE3) for initial grouping and optionally verify with a cryptographic hash only for final confirmation, balancing speed and collision risk. Also, emphasize the importance of logging and metrics for observability in production.

1. Clarify Requirements and Constraints

Ask about expected directory sizes, file types, performance requirements, and whether symlinks or special files should be followed. Confirm that the tool should return groups of duplicates and handle errors gracefully.

2. Design the Multi-Pass Algorithm

Outline a three-pass approach: 1) Recursively walk the directory, collecting file paths and sizes, skipping files that cause permission errors. 2) Group files by size, discarding groups with only one file. 3) For each size group, compute a hash of each file's content using streaming, then group by hash.

3. Address Large Files and Memory Efficiency

Explain that files are read in chunks (e.g., 64KB) to compute the hash without loading the entire file into memory. Mention that you might use a rolling hash or sample the beginning and end for very large files as an optimization, but be cautious about false positives.

4. Handle Errors and Race Conditions

Describe how to catch and log permission errors, file-not-found errors, and other I/O exceptions during traversal and hashing. For files that change mid-scan, detect by comparing size and modification time before and after hashing, and either skip or retry.

5. Discuss Trade-offs and Optimizations

Talk about hash algorithm choice (speed vs. collision resistance), concurrency (parallel hashing with a thread pool), and memory usage. Consider whether to store hashes in memory or use an external sort for very large datasets.

Key Points to Mention

  • Use streaming I/O to hash files in chunks, avoiding loading entire files into memory.
  • Group by size first to reduce the number of files that need hashing.
  • Handle permission errors and other I/O exceptions gracefully, logging them and continuing.
  • Detect files changing mid-scan by checking metadata (size, mtime) before and after hashing.
  • Choose an appropriate hash function (e.g., BLAKE3, xxHash) balancing speed and collision resistance.
  • Consider concurrency and memory trade-offs, and possibly use an external sort for scalability.

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

Q2

Is this workload I/O-bound or CPU-bound, and how would you figure out which one it is?

Technical Trade-offsSystem Design
Author's notes

Said I/O-bound pretty quickly since you're reading from disk constantly, and hashing is relatively cheap.

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AI HintsAI Generated

Suggested Approach

Start by clarifying that the answer depends on the specific workload and that you would measure rather than guess. Then walk through a systematic process: profile the workload, interpret the results, and use that to guide optimization decisions. Emphasize that the distinction matters because it determines whether you focus on reducing I/O latency/throughput or optimizing CPU efficiency.

Pro tip: Mention that many real-world workloads are mixed, so the goal is to identify the dominant bottleneck and its impact on overall performance. Also, note that the answer can change with scale, data size, or hardware, so re-evaluate after changes.

1. Define the workload and success metrics

Clarify what the workload does and what performance metric matters (e.g., latency, throughput, resource utilization). This sets the context for interpreting profiling data.

2. Measure with profiling tools

Use system-level tools (top, iostat, vmstat, perf) and application-level profilers to collect CPU usage, disk I/O, network I/O, and memory metrics. Look for signs like high CPU utilization vs. high I/O wait.

3. Analyze the bottleneck

Determine if the workload is spending most time waiting on I/O (e.g., high iowait, low CPU) or actively computing (e.g., high CPU, low I/O). Consider Amdahl's Law and the critical path.

4. Validate with controlled experiments

Run experiments: e.g., increase CPU speed or add more cores to see if performance improves (CPU-bound), or use faster storage/network to see if that helps (I/O-bound).

5. Optimize accordingly and re-evaluate

Based on the findings, apply targeted optimizations (e.g., caching, async I/O, parallelization, algorithm improvements) and re-measure to confirm the bottleneck has shifted.

Key Points to Mention

  • CPU-bound: workload spends most time executing instructions; performance improves with faster CPU or more cores.
  • I/O-bound: workload spends most time waiting for data from disk, network, or other external sources; performance improves with faster I/O or concurrency.
  • Tools: top/htop, iostat, vmstat, perf, strace, application profilers (e.g., cProfile, JProfiler).
  • Metrics: CPU utilization, iowait, disk queue length, network throughput, latency percentiles.
  • Amdahl's Law: speedup limited by the non-optimized portion; helps prioritize.
  • Real-world workloads are often mixed; identify the dominant bottleneck and consider pipelining or overlapping I/O with computation.

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

Q3

How would you handle deduplication across millions or billions of files?

System DesignTechnical Trade-offs
Author's notes

This is where it got interesting.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: scale, file types, acceptable false positive rate, and performance constraints. Then propose a multi-stage deduplication pipeline using cryptographic hashing for exact duplicates and locality-sensitive hashing for near-duplicates, discussing trade-offs between accuracy, cost, and latency. Finally, address scalability with distributed processing and storage optimizations.

Pro tip: Mention that deduplication is often a trade-off between recall and precision; in practice, you might use a two-tier approach where a fast, approximate filter (e.g., Bloom filter) reduces the candidate set before exact verification. Also, consider the cost of false positives in the context of the application.

1. Clarify Requirements

Ask about scale (number of files, total size), file types (text, binary, media), definition of duplicate (exact vs. near), and performance goals (throughput, latency, cost).

2. Choose Hashing Strategy

For exact duplicates, use cryptographic hashes like SHA-256; for near-duplicates, use locality-sensitive hashing (e.g., MinHash, SimHash) or perceptual hashes for media. Discuss collision probabilities and trade-offs.

3. Design Scalable Pipeline

Propose a distributed architecture: parallel hashing, sharding by hash prefix, and using a distributed key-value store (e.g., Cassandra, Bigtable) to track hashes. Consider batch vs. stream processing.

4. Optimize Storage and Lookup

Use Bloom filters to quickly skip non-duplicates, and store only hashes (not full files) for comparison. Discuss memory vs. disk trade-offs and potential for false positives.

5. Address Trade-offs and Edge Cases

Discuss handling hash collisions, security (e.g., salted hashes), incremental updates, and deletion. Mention monitoring and metrics for deduplication rate and false positives.

Key Points to Mention

  • Cryptographic hashing (SHA-256) for exact duplicates and its collision resistance.
  • Locality-sensitive hashing (MinHash, SimHash) for near-duplicate detection.
  • Distributed processing frameworks (MapReduce, Spark) for scalability.
  • Bloom filters for efficient pre-filtering of non-duplicates.
  • Trade-offs between false positives and false negatives, and their impact.
  • Storage optimization: storing hashes instead of full files, and using distributed databases.

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

Q4

How would you parallelize the directory scan and the hashing stages?

System DesignTechnical Trade-offs
Author's notes

Went with a producer-consumer setup, separate thread pools for scanning vs hashing since they have different bottlenecks.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and constraints, such as the scale of the directory tree, file sizes, and I/O characteristics. Then propose a pipeline architecture where directory scanning and hashing are decoupled using concurrent workers and bounded queues, and discuss trade-offs like backpressure, resource contention, and error handling.

Pro tip: Emphasize that the optimal design depends on the workload: for many small files, parallelize scanning and hashing across multiple threads; for few large files, overlap I/O and CPU with asynchronous I/O or a thread pool. Also mention that you'd measure and iterate rather than assume.

1. Clarify requirements and constraints

Ask about the expected scale (number of files, directory depth), file size distribution, storage type (SSD/HDD/network), and performance goals. This determines whether the bottleneck is I/O, CPU, or both.

2. Design a pipelined architecture

Propose a producer-consumer model: a scanner thread (or pool) traverses directories and enqueues file paths; a pool of hashing workers dequeues paths and computes hashes. Use a bounded queue to manage memory and apply backpressure.

3. Choose concurrency primitives and tune

Select thread pools, async I/O, or processes based on language and workload. Tune the number of workers and queue size to balance CPU utilization and I/O throughput, avoiding excessive context switching or memory blowup.

4. Address trade-offs and failure modes

Discuss trade-offs: parallelism vs. complexity, ordering guarantees, error handling (e.g., permission errors, missing files), and resource contention. Consider using a work-stealing scheduler or dynamic load balancing.

5. Propose monitoring and iteration

Suggest instrumenting the pipeline with metrics (throughput, latency, queue depth) and iterating based on profiling. Mention that the design should be adaptable to different workloads.

Key Points to Mention

  • Producer-consumer pattern with bounded queues for backpressure
  • Thread pool sizing based on I/O vs. CPU-bound nature of hashing
  • Asynchronous I/O or non-blocking I/O for overlapping scanning and hashing
  • Trade-offs between parallelism, complexity, and resource usage
  • Error handling and fault tolerance in concurrent environments
  • Performance measurement and iterative tuning

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

Q5

How would you support near-realtime duplicate detection as files are created or modified?

System DesignAdaptability & Ambiguity
Author's notes

Honestly the follow-up i was least prepared for.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: what 'near-realtime' means (latency target), scale (files per second, total corpus size), and what constitutes a duplicate (exact byte match, content similarity, or semantic). Then propose a pipeline that extracts content fingerprints (e.g., cryptographic hashes for exact duplicates, MinHash/SimHash for near-duplicates) and indexes them in a low-latency store (e.g., Redis, Elasticsearch) with incremental updates triggered by file events. Finally, discuss trade-offs between accuracy, latency, and cost, and how to handle updates/deletes.

Pro tip: Mention that you'd start with a simple exact-hash approach and only add fuzzy matching if needed, because premature complexity is a common failure mode in duplicate detection systems. Also, highlight the importance of idempotent processing and backpressure to handle bursts.

1. Clarify requirements and constraints

Ask about latency expectations, scale (files/sec, total files), duplicate definition (exact vs. near), and whether detection should be synchronous or asynchronous. This ensures you design the right solution.

2. Design the fingerprinting strategy

Choose an appropriate fingerprinting method: cryptographic hashes (e.g., SHA-256) for exact duplicates, or locality-sensitive hashing (e.g., MinHash, SimHash) for near-duplicates. Consider chunking for large files to enable partial matching.

3. Build the indexing and lookup layer

Select a low-latency store (e.g., Redis, Elasticsearch) that supports fast approximate nearest neighbor search if needed. Design the index schema to map fingerprints to file metadata and support efficient duplicate queries.

4. Integrate with file events and pipeline

Use a file system watcher (e.g., inotify, FSEvents) or a message queue to trigger fingerprinting and indexing as files are created/modified. Ensure the pipeline is scalable, fault-tolerant, and handles updates/deletes.

5. Address trade-offs and operational concerns

Discuss trade-offs between accuracy, latency, and cost; handle false positives/negatives; and plan for monitoring, backpressure, and idempotency. Consider how to evolve the system as scale grows.

Key Points to Mention

  • Latency targets and scale requirements (e.g., sub-second detection, thousands of files per second)
  • Fingerprinting techniques: exact hashes vs. locality-sensitive hashing (MinHash, SimHash)
  • Indexing and storage: Redis, Elasticsearch, or specialized vector databases for fast lookup
  • Event-driven architecture: file watchers, message queues (Kafka, RabbitMQ), and stream processing
  • Handling updates and deletes: versioning, tombstoning, and re-indexing strategies
  • Trade-offs: accuracy vs. speed, cost of false positives, and scalability considerations

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