Interview Guides

Oscar Health DevOps Engineer Interview Questions 2026

Oscar HealthDevOps Engineer

Updated Jun 11, 2026

Oscar Health DevOps Engineer interview questions & guide 2026

Every question Oscar Health interviewers actually ask, the frameworks that win the room, and the language hiring managers respond to.

Question bank

What is a DevOps Engineer at Oscar Health?

At Oscar Health, technology is not just a supporting department; it is the core driver of the company's mission to refactor healthcare. As a DevOps Engineer, you play a vital role in building, scaling, and securing the cloud-native infrastructure that powers health insurance for over a million members. This role sits at the intersection of software engineering and systems operations, ensuring that internal developers can ship code rapidly, safely, and in compliance with strict healthcare regulations like HIPAA.

Your work directly impacts the reliability of critical systems, from the member-facing mobile applications and telemedicine platforms to the complex backend claims-processing engines. Oscar Health relies on a modern cloud stack to manage massive datasets and real-time transactions. This means you will design self-healing infrastructure, manage automated deployment pipelines, and build tooling that enables engineering teams to own their services from development to production.

This position is highly collaborative and technically demanding. You are not merely managing servers; you are engineering systems that must remain resilient under load while maintaining absolute data integrity. If you are passionate about treating infrastructure as code, solving complex distributed systems problems, and making a tangible impact on the healthcare industry, this role offers an incredibly rewarding engineering challenge.

Common Interview Questions

To succeed in the Oscar Health hiring process, you must be prepared for a wide range of technical challenges. The interview queries are designed to test your core systems knowledge, software engineering capabilities, and architectural thinking. While questions may vary by team and seniority, the following categories represent the patterns established in real interviews for the DevOps Engineer role.

Systems & Cloud Infrastructure

This category evaluates your fundamental knowledge of operating systems, networking, and cloud platforms. Interviewers want to see that you understand the underlying mechanics of the platforms you build on.

Explain the step-by-step process of what happens when a user requests a secure webpage in their browser, from DNS resolution to rendering.
How do you diagnose a high CPU usage issue on a Linux server when standard monitoring tools do not point to a specific process?

Describe how you would secure a multi-tier web application deployed in AWS using security groups, network ACLs, and private subnets.
What are the differences between hard links and soft links in Linux, and how do they interact with the file system's inode structure?
How does Docker isolate processes, and what are the security implications of running containers with root privileges?

Software Engineering & Algorithms

Oscar Health places a strong emphasis on coding proficiency for its infrastructure roles. You will face algorithmic coding challenges designed to test your ability to write clean, efficient, and maintainable software.

Given an array of integers, write a function to find the contiguous subarray with the largest sum.
How would you write a script in Python or Go to parse a massive application log file, extract specific error metrics, and format them into a JSON payload?
Design a rate-limiter class that can be integrated into an API gateway to prevent denial-of-service attacks.
Explain how you would implement a depth-first search (DFS) algorithm to traverse a dependency graph of microservices.
Write a program that takes an IP address block in CIDR notation and returns the list of all valid host IP addresses within that subnet.

Systems Troubleshooting & Architecture

These questions assess your ability to design scalable systems and debug complex, distributed failures under pressure.

Design a highly available, fault-tolerant deployment pipeline for a microservice architecture that deploys hundreds of times per day.
A critical service is experiencing intermittent 504 Gateway Timeout errors. Walk me through your debugging methodology to locate the root cause.
How would you migrate a legacy, stateful application to a stateless containerized platform on Kubernetes with zero downtime?
Describe your strategy for managing secrets and sensitive configuration data across development, staging, and production environments.
How do you design and implement automated database backups and disaster recovery plans for a highly regulated financial or healthcare application?

Deep Dive into Evaluation Areas

To excel in the Oscar Health interview, you must understand exactly what the interviewers are looking for in each specialized round. The technical loops are structured to evaluate specific core competencies.

Systems Engineering & Cloud Infrastructure

This evaluation area focuses on your ability to design, deploy, and maintain stable, scalable infrastructure. You will be tested on your practical experience with modern cloud platforms and systems administration.

Be ready to go over:

Linux Internals – Process management, memory allocation, system calls, and troubleshooting tools like strace, lsof, and tcpdump.
AWS Architecture – Designing secure, scalable networks, managing IAM policies, and utilizing core services such as VPC, EC2, ECS, and EKS.
Infrastructure as Code – Writing clean, modular Terraform configurations, managing state files in team environments, and implementing CI/CD pipelines.
Advanced concepts (less common) – Multi-region disaster recovery, hybrid cloud networking, and custom Kubernetes controller design.

Example scenarios:

"Design a secure VPC architecture for a microservices application that requires strict compliance isolation."
"Explain how you would troubleshoot a containerized application that is intermittently running out of memory."
"How would you structure a Terraform project to manage infrastructure across multiple environments with minimal code duplication?"

Software Engineering & Algorithms

Unlike traditional systems administration roles, the DevOps Engineer position at Oscar Health requires strong programming capabilities. You will write code in a live environment, often with a software engineer who will evaluate your logic, code structure, and algorithmic efficiency.

Be ready to go over:

Data Structures – Effective use of arrays, hash maps, trees, and graphs to solve computational problems.
Algorithmic Efficiency – Analyzing time and space complexity using Big O notation and optimizing code for performance.
Scripting & Automation – Writing robust, error-tolerant scripts in Python, Go, or Bash to automate complex systems tasks.
Advanced concepts (less common) – Concurrency models, asynchronous programming, and building custom CLI tools.

Example scenarios:

"Write a function to merge overlapping IP address ranges from a list of subnets."
"Implement a log parser that extracts and aggregates response times, outputting the top 5 slowest endpoints."
"Code an algorithm to detect circular dependencies in a system deployment configuration."

Case Study & Take-Home Assignment

The take-home assignment and case study rounds assess your ability to execute a technical project independently. Your submission will be reviewed for code quality, architectural decisions, and operational readiness.

Be ready to go over:

Code Quality & Testing – Writing clean, self-documenting code with comprehensive unit and integration tests.
Operational Best Practices – Including Dockerfiles, README documentation, basic monitoring hooks, and clear instructions for running the code.
Error Handling – Ensuring your code gracefully handles unexpected inputs, network timeouts, and resource constraints.
Advanced concepts (less common) – Integrating linting, static analysis, and automated security scanning into your submission.

Example scenarios:

"Build a lightweight microservice that queries an external API, caches the results, and exposes a health check endpoint."
"Write an automation script that provisions a local development environment using Docker Compose and configures a mock database."
"Refactor a provided, buggy codebase to ensure it handles high-concurrency requests without deadlocking."

Key Responsibilities

As a DevOps Engineer at Oscar Health, your day-to-day activities will span across coding, architectural design, and operational support. You will be embedded within or closely aligned with product engineering teams to help them deliver software safely and efficiently.

Your primary deliverable is the platform itself. You will design and implement the continuous integration and continuous deployment (CI/CD) pipelines that allow developers to ship code to production with confidence. This involves building automated testing frameworks, deployment gates, and rollback mechanisms that minimize downtime and prevent regressions.

Collaboration is a cornerstone of this role. You will work alongside software engineers to architect new services, ensuring they are designed with scalability, observability, and security in mind from day one. You will also partner with security and compliance teams to ensure that all infrastructure meets HIPAA regulations, implementing automated compliance checks and robust audit logging across all environments.

Additionally, you will share operational ownership of the platform. This includes participating in an on-call rotation, defining service level objectives (SLOs), and building comprehensive monitoring and alerting systems using tools like Prometheus, Grafana, and Datadog. When incidents occur, you will lead the troubleshooting efforts and conduct blameless post-mortems to ensure the team learns from every failure.

Role Requirements & Qualifications

To be competitive for the DevOps Engineer position at Oscar Health, you must possess a strong blend of systems engineering expertise and software development skills. The hiring team looks for candidates who can bridge the gap between operations and development.

Technical Skills

Must-have skills – Proficient in at least one major programming language (Python, Go, or Java); deep hands-on experience with AWS; strong knowledge of Linux systems administration; experience managing containerized applications with Docker and Kubernetes; proficiency with Terraform for infrastructure provisioning.
Nice-to-have skills – Experience working in a highly regulated environment (healthcare or finance); familiarity with service mesh technologies like Istio; experience with advanced monitoring and APM tools (Datadog, New Relic); contribution to open-source infrastructure projects.

Experience & Soft Skills

Professional Experience – Typically requires 3+ years of experience in a DevOps, SRE, or Systems Engineering role in a cloud-native environment.
Collaboration – Proven ability to work closely with software developers to improve the software development lifecycle.
Problem-Solving – A methodical approach to troubleshooting complex, distributed systems and a passion for automation over manual intervention.
Communication – Strong written and verbal communication skills, with the ability to explain technical concepts to non-technical stakeholders.

Frequently Asked Questions

Q: How difficult is the DevOps Engineer interview process at Oscar Health? A: The process is highly rigorous and generally rated as difficult. It requires strong software engineering skills in addition to systems administration and cloud architecture knowledge. You will face live coding rounds that are comparable to software engineering interviews.

Q: How much time should I spend on the take-home assignment? A: While recruiters may state that the assignment should take around 3 hours, successful candidates often spend more time to ensure their code is production-grade, thoroughly tested, and well-documented. Do not rush the assignment, as even minor bugs can lead to rejection.

Q: What is the development stack used by the DevOps team at Oscar Health? A: The infrastructure is primarily hosted on AWS, managed using Terraform, and containerized using Docker and Kubernetes. Coding and automation are typically done in Python and Go, with a strong emphasis on modern CI/CD practices.

Q: How long does the entire hiring process take from start to finish? A: The process can be quite long, often taking between 3 to 6 weeks depending on scheduling. It involves multiple stages, including a take-home test and a comprehensive 4.5-hour virtual onsite panel with several interviewers.

Q: What is the hybrid/remote work policy for DevOps Engineers at Oscar Health? A: Oscar Health offers flexible working arrangements, with many engineering roles being remote-friendly within the United States. However, specific team preferences and office-centric hubs (such as New York City, Tempe, or Los Angeles) may influence the requirements for your specific role.

Other General Tips

To maximize your chances of success, keep these practical, insider tips in mind as you navigate the Oscar Health interview process:

Prepare for unexpected interview formats: Be highly adaptable. Candidates have occasionally reported that rounds scheduled as behavioral interviews turned out to be highly technical sessions focusing on Linux commands and AWS architecture. Keep your technical knowledge sharp for every single round.

Note

Do not let guard down during rounds labeled as "non-technical." Always be prepared to discuss technical architecture, system internals, or coding concepts.

Treat the take-home test like production code: When completing the take-home assignment, write comprehensive unit tests, handle edge cases gracefully, and write a detailed README file explaining your architectural choices, assumptions, and instructions on how to run and test your code.

Tip

A clean, well-documented project with tests stands out far more than a complex solution that lacks basic documentation or error handling.

Brush up on your software engineering fundamentals: Do not assume that because this is a DevOps role, the coding rounds will be simple scripting tests. You will likely be interviewed by software engineers who will evaluate your code using the same standards they use for core developers, including data structures and algorithmic efficiency.
Communicate your thought process clearly: During live coding and system design rounds, talk through your reasoning. Interviewers are as interested in how you approach a problem, structure your thoughts, and handle trade-offs as they are in your final solution.
Highlight your experience with automation: Throughout your interviews, emphasize how you have used automation to eliminate manual tasks, improve developer velocity, and increase system reliability in your previous roles.

Summary & Next Steps

The DevOps Engineer position at Oscar Health is an exceptional opportunity for engineers who want to apply their systems and software development skills to make a real-world impact. By ensuring the reliability, security, and scalability of the platform, you will directly support the delivery of high-quality healthcare technology to over a million members.

To succeed in this rigorous interview process, you must dedicate equal preparation time to systems engineering, cloud architecture, and software development. Focus on mastering Linux internals, AWS best practices, and algorithmic coding. Approach the take-home assignment with extreme care, ensuring your submission is robust, tested, and fully documented.

The compensation data above outlines the competitive salary ranges and equity opportunities typical for engineering roles at Oscar Health. Candidates should interpret these figures as a reflection of the high technical bar and strategic importance of the DevOps Engineer role within the organization. Use this information to guide your expectations and negotiations as you progress through the final stages of the hiring process.

Prepare thoroughly, stay adaptable during the interviews, and demonstrate your passion for building resilient systems. For additional community insights, real interview questions, and preparation resources, explore the engineering guides available on Dataford. Good luck with your preparation!

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Interview Guides

Oscar Health DevOps Engineer interview questions & guide 2026

What is a DevOps Engineer at Oscar Health?

Common Interview Questions

Systems & Cloud Infrastructure

Software Engineering & Algorithms

Systems Troubleshooting & Architecture

The questions most likely to come up

See how a strong candidate would approach this

Prioritizing Across Competing Client Projects

Getting Ready for Your Interviews

Tip

Interview Process Overview

The interview process, end to end

Note

Deep Dive into Evaluation Areas

Systems Engineering & Cloud Infrastructure

Software Engineering & Algorithms

Case Study & Take-Home Assignment

What they actually test for

Key Responsibilities

Role Requirements & Qualifications

Technical Skills

Experience & Soft Skills

Frequently Asked Questions

Other General Tips

Note

Tip

Summary & Next Steps

Other roles at Oscar Health