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Openai·Software Engineer·Technical Phone Screen·Senior

Senior
Apr 2026

Summary

Coding round at OpenAI for a software engineering role. The problem was an IP address iterator with CIDR support, which sounds manageable until you're actually in it and realize there are a dozen edge cases waiting to bite you.

Questions Asked (2)

Q1

Extend an IPv4 iterator class to support next() and prev() traversal over the full 32-bit address space, returning addresses as strings with wrap-around at both ends.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

The base version felt fine.

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AI HintsAI Generated

Suggested Approach

Clarify the requirements and constraints, then design the iterator using a 64-bit integer to represent the current address, with modular arithmetic for wrap-around. Implement next() and prev() by incrementing or decrementing the integer and converting to the dotted-decimal string format, ensuring proper handling of the boundaries.

Pro tip: Mention that using a 64-bit integer avoids overflow issues and simplifies wrap-around logic, and discuss the trade-offs between storing the address as an integer versus storing it as a string for performance and memory.

1. Clarify Requirements

Ask about the expected input/output format, whether the iterator should be bidirectional, and if wrap-around is required at both ends. Confirm that the full 32-bit address space (0.0.0.0 to 255.255.255.255) must be supported.

2. Choose Internal Representation

Decide to store the current address as a 64-bit unsigned integer to avoid overflow when incrementing or decrementing. Explain that this simplifies modular arithmetic for wrap-around.

3. Implement next() and prev()

For next(), increment the integer by 1 and take modulo 2^32. For prev(), decrement by 1 and if negative, add 2^32. Convert the integer to dotted-decimal string for return.

4. Handle Conversion and Edge Cases

Write helper functions to convert between integer and string representations. Ensure that 0.0.0.0 and 255.255.255.255 wrap correctly. Test with edge cases like starting at boundaries.

5. Discuss Trade-offs and Optimizations

Mention alternative representations (e.g., storing four bytes) and compare performance. Discuss thread safety if needed, and whether to precompute strings for caching.

Key Points to Mention

  • Use of 64-bit integer to prevent overflow and simplify wrap-around.
  • Modular arithmetic: (current + 1) % 2^32 for next, (current - 1 + 2^32) % 2^32 for prev.
  • Conversion between integer and dotted-decimal string format.
  • Edge cases: wrap-around at 0.0.0.0 and 255.255.255.255.
  • Trade-offs: integer vs. byte array vs. string storage; performance and memory considerations.
  • Thread safety and iterator state management if multiple threads access.

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

Q2

Extend the same iterator to accept a CIDR block at construction (like '192.168.0.0/24') and constrain both forward and backward traversal strictly within that address range.

Algorithms & Data StructuresTechnical Trade-offsAPI & Integrations
Author's notes

This is where things got messier for me.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the iterator's current design and the requirements for CIDR support, then outline a strategy to parse the CIDR block into a network address and prefix length, and use bitwise operations to compute the start and end addresses. Explain how you would modify the iterator's next() and previous() methods to check bounds and stop traversal when reaching the limits, and discuss trade-offs between precomputing bounds versus computing on the fly.

Pro tip: Mention that you would handle edge cases like /0 and /32 (or /128 for IPv6) and ensure the iterator is inclusive of the network and broadcast addresses, as this shows attention to detail and real-world networking knowledge.

1. Clarify requirements and existing iterator

Ask whether the iterator currently supports forward and backward traversal and what the expected behavior is when reaching the CIDR boundaries (e.g., stop, throw exception, or wrap). Confirm if IPv6 support is needed.

2. Parse CIDR and compute bounds

Explain how to parse the CIDR string into an IP address and prefix length, then compute the network address (start) and broadcast address (end) using bitwise operations. For IPv4, mask the IP with the prefix mask to get the start, and set the host bits to 1 to get the end.

3. Integrate bounds into iterator logic

Modify the iterator's constructor to accept the CIDR block and store the start and end addresses. In next() and previous(), check if the next address would exceed the bounds; if so, signal exhaustion (e.g., return null or throw StopIteration).

4. Handle edge cases and efficiency

Discuss handling /0 (entire address space) and /32 (single address), and ensure the iterator works correctly for both. Consider precomputing bounds to avoid recalculating on each call, and mention potential overflow issues when incrementing addresses.

5. Test and validate

Outline a testing strategy: verify forward and backward traversal within a CIDR, check boundary conditions (first and last addresses), and test with different prefix lengths. Also consider concurrency if the iterator is shared.

Key Points to Mention

  • CIDR parsing: splitting into IP and prefix, converting IP to integer for bitwise operations.
  • Computing network and broadcast addresses: using bitwise AND with mask for start, and OR with inverted mask for end.
  • Iterator design: maintaining current position, checking bounds in next() and previous(), and defining exhaustion behavior.
  • Edge cases: /0, /32 (or /128), and handling of network and broadcast addresses inclusively.
  • Performance considerations: precomputing bounds, avoiding repeated parsing, and efficient increment/decrement.
  • API consistency: ensuring the extended iterator remains compatible with existing usage and follows the same interface.

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