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OpenAI·Software Engineer·Technical Phone Screen·Intermediate

IntermediatePrefer not to say
Jul 2026

Summary

Interviewed for a software engineering role at OpenAI and got a problem set built around IPv4 address iteration. Four parts, each building on the last, ending with an open-ended optimization discussion. Felt pretty solid on the first two but the CIDR bitmasking tripped me up more than I expected.

Questions Asked (4)

Q1

Implement a Python class that iterates forward through IPv4 addresses starting from a given IP up to 255.255.255.255, using the iterator protocol.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

This part was fine.

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AI HintsAI Generated

Suggested Approach

Implement a class that converts the starting IP to a 32-bit integer, then uses __iter__ to return self and __next__ to increment and yield the next IP until 255.255.255.255, raising StopIteration. Convert back to dotted string format for each yield.

Pro tip: Mention that using integer arithmetic avoids string parsing overhead and edge cases, and explicitly handle the terminal condition to prevent infinite loops. Also, note that the iterator is stateful and not reentrant, which is typical for iterators.

1. Clarify requirements and constraints

Confirm that the iterator should start at the given IP inclusive and stop after yielding 255.255.255.255. Ask if the input is guaranteed valid or if validation is needed.

2. Design the internal representation

Convert the starting IP to a 32-bit integer to simplify incrementing and boundary checks. Store this integer as the current state.

3. Implement the iterator protocol

Define __iter__ to return self and __next__ to check if the current integer exceeds 0xFFFFFFFF; if so, raise StopIteration. Otherwise, convert the current integer to dotted string, increment the integer, and return the string.

4. Handle edge cases and validation

Ensure the starting IP is valid and not greater than 255.255.255.255. Consider what happens if the start IP is already 255.255.255.255 (should yield once then stop).

5. Test and discuss trade-offs

Walk through examples, test boundaries, and discuss time/space complexity (O(1) per iteration, O(1) space). Mention alternative string-based approaches and why integer is better.

Key Points to Mention

  • Iterator protocol: __iter__ returns self, __next__ raises StopIteration when exhausted.
  • Integer representation of IP addresses for efficient increment and comparison.
  • Conversion between dotted string and integer using bit shifts and masking.
  • Boundary condition: stop after yielding 255.255.255.255 (0xFFFFFFFF).
  • Input validation: ensure starting IP is a valid IPv4 address and not beyond the limit.
  • Time and space complexity: O(1) per iteration, O(1) extra space.

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

Q2

Now implement a reverse iterator that starts from a given IP and counts down to 0.0.0.0.

Algorithms & Data Structures
Author's notes

Basically the same structure flipped.

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AI HintsAI Generated

Suggested Approach

Clarify the IP representation (e.g., IPv4 as a 32-bit integer) and the iterator protocol expected (e.g., Python's __iter__/__next__). Then implement the iterator by converting the IP to an integer, decrementing until 0.0.0.0, and converting back to dotted-decimal format.

Pro tip: Mention edge cases like starting at 0.0.0.0 (should yield nothing or just 0.0.0.0?) and ensure the iterator is memory-efficient by not precomputing all IPs. Also, discuss thread safety if relevant.

1. Clarify requirements

Ask whether the IP is IPv4 or IPv6, and confirm the iterator protocol (e.g., Python's iterator protocol). Clarify if the starting IP is inclusive and if 0.0.0.0 should be yielded.

2. Choose representation

Decide to represent the IP as a 32-bit integer for easy arithmetic. Explain conversion from dotted-decimal to integer and back.

3. Implement iterator

Create a class with __iter__ returning self and __next__ that decrements the integer until it reaches -1 (or 0 if inclusive) and raises StopIteration. Convert the integer to dotted-decimal string for each yield.

4. Handle edge cases

Consider starting IP 0.0.0.0: if inclusive, yield it once then stop; if exclusive, yield nothing. Also handle invalid IPs and ensure no overflow/underflow.

5. Test and optimize

Write tests for typical and edge cases. Discuss time complexity O(n) where n is number of IPs, and space O(1). Mention potential optimizations like using generators.

Key Points to Mention

  • IP address as 32-bit integer for arithmetic
  • Iterator protocol: __iter__ and __next__ (or generator)
  • Conversion between dotted-decimal and integer
  • Edge cases: start at 0.0.0.0, inclusive/exclusive bounds
  • Time and space complexity: O(n) time, O(1) space
  • Thread safety and reusability considerations

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

Q3

Given a CIDR string like '192.168.1.0/24', use bitwise operations to compute the start and end IP of the range, then iterate through all addresses in it.

Algorithms & Data StructuresTechnical Trade-offs
Author's notes

This is where I slowed down.

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AI HintsAI Generated

Suggested Approach

Start by explaining the bitwise operations to compute the network address and broadcast address from the CIDR. Then describe how to iterate through the range, converting between integer and IP string representations. Emphasize efficiency and handling edge cases like /0 and /32.

Pro tip: Mention that using 32-bit unsigned integers avoids sign issues and that iterating with a simple loop is fine for small ranges, but for large ranges consider using a generator to avoid memory issues.

1. Parse CIDR and compute mask

Split the CIDR into IP and prefix length. Convert IP to a 32-bit integer and compute the subnet mask by shifting 1 left by (32 - prefix) and subtracting 1, then complementing.

2. Calculate network and broadcast addresses

Perform bitwise AND between IP and mask to get the network address (start). Perform bitwise OR between network address and the inverse mask to get the broadcast address (end).

3. Iterate through addresses

Loop from start to end inclusive, converting each integer back to dotted-decimal format. Optionally, use a generator to yield addresses lazily.

4. Handle edge cases and efficiency

Discuss handling /0 (entire IPv4 space) and /32 (single address). Mention that iterating over huge ranges (e.g., /8) may be impractical, so consider using a generator or discussing trade-offs.

Key Points to Mention

  • Bitwise operations: AND for network address, OR with inverted mask for broadcast address.
  • Conversion between IP string and 32-bit integer (e.g., using struct or manual shifting).
  • Subnet mask calculation: mask = (1 << (32 - prefix)) - 1, then invert.
  • Iteration: simple loop from start to end, converting each integer to IP string.
  • Edge cases: /0, /32, and large ranges; use of generators for memory efficiency.
  • Time complexity: O(2^(32-prefix)) for iteration, which is exponential in prefix length.

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

Q4

How would you optimize the time and space complexity of these iterators for very large CIDR ranges, like /8 or /0?

Technical Trade-offsSystem Design
Author's notes

I talked about lazy evaluation being the whole point of an iterator so memory is already O(1).

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AI HintsAI Generated

Suggested Approach

Start by clarifying the iterator's contract (lazy vs eager, ordering, mutation) and the actual bottleneck for huge ranges. Then propose a lazy, streaming design that avoids materializing the full range, using arithmetic/bitwise operations to compute the next address in O(1) time and O(1) space, and discuss trade-offs like skipping, parallelism, and memory-mapped or chunked processing.

Pro tip: Emphasize that for /0 or /8, the number of addresses can exceed 2^32, so any eager collection is infeasible; show you'd benchmark with realistic access patterns (sequential, random, skip) and consider external iteration or generator-based APIs to keep memory flat.

1. Clarify requirements and constraints

Ask about iterator semantics: must it be lazy, ordered, support multiple passes, or handle concurrent modification? Confirm the expected range sizes and whether the consumer can process addresses in chunks.

2. Identify the complexity bottleneck

Explain that naive implementations often materialize the range (O(n) space) or recompute prefixes (O(n) time). For /0, n = 2^32, so both time and space must be O(1) per iteration step.

3. Design a lazy, arithmetic iterator

Propose representing the CIDR as a start address and a count, then using integer increment and bitwise masking to yield the next address in O(1) time and O(1) space, with no precomputed list.

4. Optimize for large ranges and access patterns

Discuss chunking (e.g., process 2^20 addresses at a time), skipping via arithmetic jumps, and parallelizing by splitting the range into sub-ranges, while keeping memory bounded.

5. Validate and discuss trade-offs

Mention benchmarking with realistic workloads, handling edge cases (overflow, endianness), and trade-offs between simplicity, speed, and memory for different use cases (e.g., streaming vs random access).

Key Points to Mention

  • Lazy evaluation and generators to avoid materializing the entire range
  • O(1) time and space per iteration using arithmetic and bitwise operations
  • Chunking or batching to reduce per-item overhead and improve cache locality
  • Parallelization by partitioning the CIDR range into independent sub-ranges
  • Handling integer overflow and using appropriate integer types (e.g., 128-bit for IPv6)
  • Trade-offs between sequential streaming and random access, and when to use external iteration

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