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Openai·Machine Learning Engineer·Technical Phone Screen·Senior

SeniorPrefer not to say
Apr 2026

Summary

Coding round for an ML Engineer role at OpenAI. One meaty implementation question that looked straightforward until the edge cases started piling up.

Questions Asked (1)

Q1

Write a function that checks whether an installed version string satisfies one or more version constraint specifiers. It should handle pre-release suffixes, missing patch/minor components, and raise errors for invalid inputs. Also discuss test cases for boundary conditions and how you'd extend the solution to support PEP 440 syntax.

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

Started confident, got humbled fast.

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AI HintsAI Generated

Suggested Approach

Start by clarifying the requirements and defining the scope, then outline a robust parsing and comparison strategy that handles version normalization and constraint checking. Emphasize edge cases and error handling, and discuss how to extend to full PEP 440 compliance with a modular design.

Pro tip: Mention that you would use a well-tested library like packaging for production, but implement a simplified version to demonstrate understanding of the underlying algorithms and trade-offs.

1. Clarify Requirements and Scope

Ask about the expected input formats, constraint operators (e.g., ==, >=, <), and whether pre-release versions should be included by default. Confirm error handling expectations for invalid inputs.

2. Design Version Parsing and Normalization

Outline a function to parse a version string into a tuple of integers and optional pre-release identifier, handling missing minor/patch by defaulting to zero. Normalize pre-release suffixes (e.g., 'a', 'b', 'rc') for comparison.

3. Implement Constraint Checking

For each constraint specifier, parse the operator and version, then compare the normalized installed version. Combine multiple constraints with logical AND, and raise ValueError for invalid specifiers.

4. Discuss Test Cases and Edge Conditions

Enumerate boundary cases: equal versions, pre-release vs release, missing components, invalid strings, and multiple constraints. Explain how to test each systematically.

5. Extend to PEP 440 and Trade-offs

Describe how to support full PEP 440 syntax (e.g., ~=, ===, wildcards, local versions) by extending the parser and comparator. Discuss trade-offs between custom implementation and using libraries like packaging.

Key Points to Mention

  • Version normalization: padding missing components with zeros and handling pre-release identifiers (e.g., '1.0a1' < '1.0').
  • Constraint operators: ==, !=, <, <=, >, >=, and their semantics with pre-releases (e.g., '>=1.0' includes pre-releases unless excluded).
  • Error handling: raising ValueError for malformed version strings or invalid operators, with clear messages.
  • Test cases: boundary conditions like '1.0' vs '1.0.0', pre-release ordering, multiple constraints, and invalid inputs.
  • PEP 440 features: compatible release (~=), wildcards (*), local version labels, and epoch segments.
  • Trade-offs: custom implementation for control vs. using packaging library for correctness and maintenance.

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