I have 6+ years in Windows/VMware infrastructure (L2 Admin) and am learning into Azure, Terraform, PowerShell, Bash, Docker and CI/CD; with my infrastructure background, should I target DevOps/Cloud first and later move into Cloud Security, or pursue Cloud Security directly?
DevOps vs Cloud Security — what would you choose in my situation?
I’m looking for real-world advice from people currently working in DevOps/Cloud/Cloud Security, especially seniors who have seen people transition between these fields.
My background
I have 6+ years of IT infrastructure experience at service MNC currently working as an L2 Windows/VMware Administrator.
Core: Windows Server, VMware/vCenter, AD, DNS/DHCP, patching, troubleshooting, ServiceNow, ITIL/BAU operations.
Transitioning into cloud: Azure, Terraform, PowerShell, Bash, Docker, Git/GitHub Actions, basic networking/Linux. AZ-104 theory largely completed.
I’m infrastructure-oriented, not a heavy-coding person, and want to move away from traditional L1/L2 support toward engineering.
My current project ends in ~1 week, so I need to decide what role to target next.
The actual dilemma
I see far more DevOps/Cloud openings than Cloud Security openings, particularly for someone transitioning from infrastructure.
DevOps seems like the more realistic immediate entry path because:
More jobs and clearer entry-level requirements
My infrastructure background transfers well
More visible roadmaps and learning resources
But I’m concerned about the long-term reality:
Constantly changing tools
Kubernetes/Terraform/Docker/CI-CD/cloud/monitoring/security, etc.
Increasingly broad SDLC responsibilities
Production pressure/on-call/rotational work in many companies
Continuous upskilling and potential tool churn
Cloud Security looks attractive long-term, but I’m struggling to reconcile that with the actual market.
I see far fewer junior Cloud Security roles, and many JDs seem to prefer people who already come from cybersecurity, IAM, SOC, network security, or experienced cloud backgrounds.
AI/research keeps suggesting Cloud Security can provide strong long-term specialization, demand, compensation and potentially better WLB — but is that actually true in the job market?
What I need help deciding
If you were in my exact position, what would you choose for the next 5–10 years?
DevOps → DevSecOps/Cloud Security
Azure Cloud/Infrastructure → Cloud Security
Cloud Operations → IAM → Cloud Security
Another route
And since I need a role now, what would you target first if Cloud Security were the eventual goal?
Would an Azure Cloud/Infrastructure, Cloud Operations, IAM, or monitoring-focused role be the smartest bridge from my current Windows/VMware background?
I’m specifically looking for answers to these:
Is Cloud Security genuinely a realistic career destination from Windows/Infrastructure → Azure, or is the entry barrier too high?
Have you personally seen someone make this transition successfully? What was their path?
Does entering DevOps first genuinely make Cloud Security easier later, or can it become a detour?
What skills actually mattered when you/people you know got their first Cloud Security role?
What does the real day-to-day work and career progression look like versus what online roadmaps suggest?
If you were restarting your career with my background, which path would you choose and what would you do in the next 12 months?
I’m not looking for generic “learn both / cloud is the future / security has demand” advice.
I want the kind of advice you would give to a younger sibling who has to make this decision now, based on actual hiring, work pressure, career progression and long-term reality.
Especially interested in perspectives from Cloud Security Engineers, DevSecOps Engineers, DevOps Engineers, Cloud Architects, Security Architects and hiring managers.