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Openai·Software Engineer·Technical Phone Screen·Intermediate

IntermediatePrefer not to say
Apr 2026Remote

Summary

Coding interview at OpenAI for a software engineer role. The environment itself caused more trouble than the actual problem, and I left wishing I'd figured out the tooling quirks before the clock started.

Questions Asked (1)

Q1

Solve the IP address parsing problem, including implementing CIDR block notation support.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

Made it to the third part (CIDR blocks) but the output was wrong and I didn't catch why until after the call ended.

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AI HintsAI Generated

Suggested Approach

Start by clarifying requirements: IPv4 vs IPv6, strictness of validation, and expected output for CIDR. Then outline a modular design: a parser for base IP addresses and a separate CIDR handler that computes network and broadcast addresses. Implement with clear error handling and discuss trade-offs like regex vs manual parsing.

Pro tip: Mention that you would write comprehensive unit tests covering edge cases like leading zeros, out-of-range octets, and CIDR prefixes at boundaries (0 and 32 for IPv4). This shows attention to detail and production readiness.

1. Clarify Requirements

Ask about supported IP versions, validation strictness, and expected output format for CIDR (e.g., network address, broadcast, or just validation).

2. Design the Parser

Decide between regex and manual parsing. For IPv4, split by dots and validate each octet; for IPv6, handle groups and compression. For CIDR, split on '/' and validate prefix length.

3. Implement Core Logic

Write functions to parse and validate IP addresses, then extend to CIDR by computing network and broadcast addresses using bitwise operations.

4. Handle Edge Cases

Cover invalid inputs, leading zeros, IPv4-mapped IPv6, and CIDR prefixes at boundaries. Ensure proper error messages.

5. Discuss Trade-offs and Testing

Compare regex vs manual parsing for performance and readability. Outline a testing strategy with unit tests for all edge cases.

Key Points to Mention

  • IPv4 vs IPv6 parsing differences and validation rules
  • CIDR notation: prefix length, network address calculation, broadcast address
  • Bitwise operations for subnet masking
  • Error handling and input validation
  • Performance considerations: regex vs manual parsing
  • Testing strategy: unit tests for edge cases

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