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Oscar Insurance DevOps Engineer Interview Questions

The questions to prepare for a Oscar Insurance DevOps Engineer interview. Questions from real interview reports rank first. Updated weekly.

18questions
~2htotal time
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1
PipelinesStart here. 7 questions · ~56 min
Manage Terraform Infrastructure DriftMedium

Approach for detecting, monitoring, and remediating drift in a Terraform-managed environment.

InfrastructureToolsQualityOscar Insurance
Consistency Across Service PipelinesMedium

Approach for keeping pipeline outputs consistent when multiple microservices publish overlapping, delayed, or duplicate data.

system designdata consistencymicroservicesOscar Insurance
Security Groups vs NACLsMedium

Tests your understanding of AWS network security controls and how you apply them to protect application tiers.

InfrastructureSecurityawsOscar Insurance
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2
Execution3 questions · ~24 min
Design a Production Rollback PlanMedium

Design a rollback plan for a failed production deployment, including triggers, ownership, validation, and safe recovery steps.

Rollback PlanSuccess CriteriaRisk AssessmentOscar Insurance
Set SLIs and SLOs for ClaimsHard

Tests your ability to define measurable reliability targets for critical production services.

Success CriteriaExecutionRisk AssessmentOscar Insurance
Multi-Region AWS High AvailabilityHard

Tests your ability to design resilient, low-latency multi-region AWS architectures for Oscar Insurance.

Trade-offsRoadmappingRisk AssessmentOscar Insurance

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3
Coding3 questions · ~24 min
Parse Logs Into JSON SummaryMedium

Tests your ability to build reliable log parsing and transformation logic for operational insights.

Hash TablesStringsTestingOscar Insurance
API Gateway Rate LimiterMedium

Tests your ability to implement defensive controls to protect APIs from abusive traffic.

Hash TablesAPIsQueueOscar Insurance
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4
Behavioral & Leadership5 questions · ~40 min
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The finish line: interview-readyComplete all 18 questions to finish this plan.