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Anthropic·Software Engineer·Onsite - Coding / Algorithms·Senior

Senior
Jul 2026

Summary

Coding round at Anthropic for a software engineer role. The main question was a file deduplication problem with a solid chunk of follow-up discussion that pushed into system design territory pretty quickly.

Questions Asked (5)

Q1

Given a list of file paths or a directory, implement a function to find duplicate files. You should first group files by size, then confirm duplicates within each group using a content hash like SHA-256.

Algorithms & Data StructuresSystem Design
Author's notes

The two-stage approach is pretty natural once you think about it: size check is basically free, so you filter down before doing any expensive I/O.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the input format (list of paths vs. directory) and whether to recurse into subdirectories. Then outline a two-phase algorithm: first group files by size to cheaply eliminate non-duplicates, then within each size group compute a cryptographic hash (e.g., SHA-256) to confirm identical content. Finally, discuss trade-offs like memory usage, I/O cost, and handling edge cases such as empty files or symlinks.

Pro tip: Mention that you can further optimize by hashing only the first few KB of each file before computing the full hash, and that you should handle race conditions if files can change during the scan.

1. Clarify requirements and constraints

Ask about input format (list vs. directory), recursion, file size limits, and whether files can be modified during the scan. Confirm the definition of 'duplicate' (byte-identical vs. same content ignoring metadata).

2. Group by size

Iterate over all files, retrieve their sizes, and build a map from size to list of file paths. This cheaply filters out files that cannot be duplicates.

3. Hash within size groups

For each size group with more than one file, compute a strong hash (e.g., SHA-256) of each file's content. Group files by their hash value to identify duplicates.

4. Handle edge cases and optimize

Consider empty files (all have same hash), symlinks (avoid infinite loops), and large files (stream hashing). Optionally, use a partial hash (first few KB) as a pre-filter before full hashing.

5. Analyze complexity and trade-offs

Discuss time complexity (O(n) file stats + O(m * average file size) for hashing) and space complexity (O(n) for maps). Mention alternatives like using a database or external sort for very large datasets.

Key Points to Mention

  • Two-phase approach: size grouping then content hashing to minimize expensive I/O.
  • Use of cryptographic hash (SHA-256) for collision resistance, but note that non-cryptographic hashes (e.g., MD5) may be faster if collisions are acceptable.
  • Streaming file reads to handle large files without loading entire content into memory.
  • Handling of edge cases: empty files, symlinks, permission errors, and files changing during scan.
  • Trade-offs between memory usage and I/O: storing all hashes in memory vs. external sorting.
  • Potential optimizations: partial hashing, parallel processing, and using file metadata (e.g., inode) to skip hard links.

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

Q2

Is file deduplication I/O-bound or CPU-bound, and how does that affect your choice between threads and processes?

Technical Trade-offsSystem Design
Author's notes

I said I/O-bound and jumped to threads, which is the right answer in Python given the GIL situation.

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AI HintsAI Generated

Suggested Approach

Start by clarifying that deduplication is a pipeline with distinct stages, each having different bottlenecks: chunking and hashing are CPU-bound, while reading and writing data are I/O-bound. Then explain that the optimal concurrency model depends on the dominant bottleneck: use processes for CPU-bound stages to bypass the GIL, and threads or async I/O for I/O-bound stages to overlap waits. Finally, discuss how a hybrid approach or pipeline parallelism can maximize throughput.

Pro tip: Mention that in practice, deduplication is often I/O-bound due to slow storage, but the hashing step can become CPU-bound with large chunks or weak hardware; therefore, profile before choosing. Also, note that using threads for I/O and processes for CPU in a pipeline can yield the best results, but beware of inter-process communication overhead.

1. Decompose the deduplication pipeline

Break deduplication into stages: reading data, chunking, hashing, comparing hashes, and writing unique data. Identify which stages are CPU-intensive (e.g., hashing) and which are I/O-intensive (e.g., reading/writing).

2. Determine the dominant bottleneck

Explain that the overall bound depends on the slowest stage. For example, if storage is slow, the process is I/O-bound; if hashing is slow, it's CPU-bound. Mention that this can vary with data size, hardware, and algorithm.

3. Map concurrency models to bottlenecks

For I/O-bound stages, threads or async I/O are efficient because they overlap waiting. For CPU-bound stages, processes are better because they bypass the GIL and utilize multiple cores.

4. Consider a hybrid or pipeline approach

Propose using a pipeline where I/O stages use threads and CPU stages use processes, or use a process pool for hashing and a thread pool for I/O. Discuss trade-offs like complexity and communication overhead.

5. Conclude with a recommendation

Summarize that the choice depends on profiling the specific workload, but a common pattern is to use processes for hashing and threads for I/O, or to use async I/O with a process pool for CPU work.

Key Points to Mention

  • The Global Interpreter Lock (GIL) in Python prevents true parallelism with threads for CPU-bound tasks.
  • I/O-bound tasks benefit from concurrency because threads release the GIL during I/O operations.
  • CPU-bound tasks benefit from parallelism using multiple processes to utilize multiple cores.
  • Deduplication involves both I/O (reading/writing) and CPU (hashing, comparing) operations.
  • Profiling is essential to identify the actual bottleneck in a given environment.
  • Hybrid approaches (e.g., threads for I/O, processes for CPU) can optimize performance but add complexity.

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

Q3

How would you handle hashing very large files efficiently? What about short-circuiting the comparison early?

Technical Trade-offsAlgorithms & Data Structures
Author's notes

Chunked reading came to me immediately.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the constraints: file size, memory limits, and whether the hash is for integrity or comparison. Then describe a streaming approach using a cryptographic hash (e.g., SHA-256) with a fixed-size buffer, and explain how to short-circuit comparisons by hashing in chunks and comparing incrementally, or by comparing file sizes and metadata first.

Pro tip: Mention that for pure equality checks, you can avoid hashing entirely by comparing files byte-by-byte with early exit on mismatch, which is often faster than hashing both files. Also note that cryptographic hashes are overkill for non-adversarial scenarios; a fast non-cryptographic hash like xxHash or BLAKE3 may suffice.

1. Clarify requirements and constraints

Ask about file size, available memory, whether the hash is for integrity, deduplication, or comparison, and if adversarial resistance is needed. This determines the choice of hash algorithm and approach.

2. Choose a streaming hash algorithm

Select a hash function that supports incremental updates (e.g., SHA-256, BLAKE3, xxHash) and read the file in fixed-size chunks (e.g., 1 MB) to keep memory usage constant.

3. Implement chunked hashing with early exit

For comparison, hash both files chunk-by-chunk and compare hashes after each chunk; if they differ, stop immediately. Alternatively, compare byte-by-byte with early exit, which can be faster for equality checks.

4. Optimize with metadata and parallelization

First compare file sizes and modification times to quickly rule out equality. For very large files, consider parallelizing hashing across multiple threads or using memory-mapped I/O for speed.

5. Discuss trade-offs and edge cases

Explain the trade-off between cryptographic security and speed, the risk of hash collisions, and how to handle files that change during hashing (e.g., using file locks or checksums).

Key Points to Mention

  • Streaming/chunked hashing to handle files larger than memory
  • Choice of hash algorithm: cryptographic (SHA-256) vs non-cryptographic (xxHash, BLAKE3) based on use case
  • Short-circuiting by comparing chunk hashes or bytes incrementally and exiting on first mismatch
  • Pre-comparison of file size and metadata to avoid unnecessary hashing
  • Parallelization and memory-mapped I/O for performance
  • Trade-offs: collision resistance, speed, and suitability for adversarial vs non-adversarial scenarios

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

Q4

If you had to scan millions of files, what are the memory and performance concerns, and how would you address them?

System DesignTechnical Trade-offs
Author's notes

Talked about not loading all paths into memory at once, batching, and parallel scanning.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements: file sizes, types, storage location, and what 'scan' entails (e.g., reading metadata vs. full content). Then discuss memory and performance concerns in terms of I/O, CPU, and memory, and propose a streaming, parallelized approach with bounded memory and backpressure.

Pro tip: Mention that you would first measure and profile to identify bottlenecks, and consider using memory-mapped files or asynchronous I/O to overlap computation and I/O. Also, discuss trade-offs between throughput and latency, and how you would handle failures and retries.

1. Clarify Requirements

Ask about file sizes, types, storage (local, distributed, cloud), and what scanning involves (metadata, content, pattern matching). Determine if the scan is one-time or continuous.

2. Identify Memory and Performance Concerns

Memory: loading all files or metadata into memory can cause OOM; large files can exceed memory. Performance: I/O bottlenecks (disk, network), CPU for processing, and concurrency overhead.

3. Design a Streaming and Parallel Architecture

Process files in a streaming fashion with bounded buffers, use a producer-consumer model with a thread/process pool, and parallelize across files or chunks. Use asynchronous I/O to avoid blocking.

4. Address Memory Management

Use memory-mapped files for large files, process data in chunks, and avoid retaining unnecessary data. Implement backpressure to prevent overwhelming the system.

5. Optimize and Handle Failures

Profile to find bottlenecks, tune concurrency levels, and use efficient data structures. Implement retries, checkpointing, and monitoring for robustness.

Key Points to Mention

  • Streaming and chunking to avoid loading entire files into memory
  • Parallelism and concurrency (threads, processes, async I/O) with bounded resource usage
  • I/O optimization: memory-mapped files, sequential reads, and avoiding random access
  • Backpressure and flow control to prevent memory exhaustion
  • Trade-offs between throughput, latency, and resource utilization
  • Failure handling: retries, idempotency, and checkpointing

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

Q5

How would you extend this system to support real-time or continuous duplicate detection as files are added or changed?

System DesignAPI & Integrations
Author's notes

This is where it got interesting.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the current system's architecture and duplicate detection method, then propose an event-driven pipeline that processes file changes in real-time. Focus on incremental detection using efficient data structures and discuss trade-offs between latency, accuracy, and resource usage.

Pro tip: Emphasize idempotency and exactly-once processing to avoid duplicate alerts, and mention how you'd handle backpressure and failures gracefully. Also, consider discussing how to bootstrap the system with existing files without downtime.

1. Clarify requirements and constraints

Ask about the expected scale, latency requirements, and whether detection should be synchronous or asynchronous. Understand the current system's duplicate detection logic and storage.

2. Design an event-driven architecture

Propose using file system watchers or change data capture to emit events on file creation/modification. Route events to a processing pipeline that performs duplicate checks.

3. Implement incremental duplicate detection

Use efficient indexing structures like hash tables or Bloom filters to quickly check for duplicates. For content-based detection, compute and compare hashes or fingerprints incrementally.

4. Ensure scalability and fault tolerance

Discuss partitioning, load balancing, and handling of failures with retries and dead-letter queues. Consider using a message broker like Kafka for durability and backpressure.

5. Address consistency and bootstrapping

Explain how to initialize the index with existing files and keep it consistent with real-time updates. Discuss strategies for handling race conditions and ensuring idempotency.

Key Points to Mention

  • Event-driven architecture with file system watchers (e.g., inotify) or CDC
  • Incremental hashing or fingerprinting for content-based duplicate detection
  • Use of efficient data structures like Bloom filters or hash tables for low-latency lookups
  • Message queues (e.g., Kafka) for decoupling, scalability, and fault tolerance
  • Idempotency and exactly-once processing to avoid duplicate alerts
  • Trade-offs between latency, accuracy, and resource consumption

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