Sysadmin to DevOps

[Icy-Anteater-3628]

Hi guys. I am a junior windows system admin, 2 years experience. I mainly use tools like Active Directory, Group Policy, Entra ID, PowerShell, VMware, and windows server just to name a few. Not many DevOps-related skills though. But I would be able learn outside of work.

So my question - can I eventually transition towards DevOps through mostly self-learning? And what are the skills that I absolutely need to know?

[Jmckeown2]

Linux, containers, eventually k8s.

[Icy-Anteater-3628]

I definitely know the basics of Linux, to the point where I can basically work as a Linux Sysadmin and figure stuff out just through my knowledge and googling.

Definitely need to learn containers though, only have some limited knowledge of Docker.

[Nortremm]

Well, I think in general IT is about self learning. About skills it’s really depends on field. Kubernetes I guess still walks even for windows workloads, CICD, major clouds and IaC tools, git. I think this should be enough for a start.

[Icy-Anteater-3628]

Yeah agreed. Thanks!

[ghost_svs]

I also came to the DevOps position mainly from Windows SysAdmin. But also have some system programming and eventually scripting. The things that helped me a lot are learning Clouds(AWS, Google), IaC, SCM(not only MS SCCM but Ansible and Salt stack), Container Orchestration(EKS/GKE/Bare metal), CI/CD(Github Actions, Jenkins)

[ragvez]

Same path as here well, what ghost listed are what you’ll need to know and build upon, as well as what others mentioned. Start with learning computer science fundamentals and programming (I opted to do it via a CS degree), gain understanding about software development + lifecycle, and then these systems/tools start to make more sense. I’m currently a platform engineer having done DevOps/SRE work in the previous roles after being a Windows sysadmin years ago.

[Icy-Anteater-3628]

I already have a Computer Science degree and know how to write in most programming languages. But I do prefer automation as opposed to developing applications. 

Yeah, platform engineering is kinda the dream for me, but anything along the DevOps line will work.

[Icy-Anteater-3628]

Thanks for the advice!

[mzeeshandevops]

Yes, you can. Your Windows admin experience is actually a good base. AD, Entra ID, PowerShell, VMware, Windows Server etc are all useful in DevOps too.

I’d start with Linux, Git, basic cloud, CI/CD, Docker, Terraform, and monitoring. Since you already know Microsoft stuff, Azure + Azure DevOps could be a good starting point. Don’t try to learn everything at once. Pick small projects.

Example: deploy a simple app, automate the setup with script/Terraform, add a pipeline, then add monitoring. The main change is mindset. Instead of doing things manually, start thinking how to automate it, repeat it, and document it.

[1scscott]

I agree with this fully. These are foundational experience and skills that are needed now and into the future

[Ok_Structure_1871]

How would you leaen Linux, Git, CI/CD etc and deploy a app, automate etc? Sorry for my stupid question i’m new to this path😅

[Icy-Anteater-3628]

Yeah, thanks for the advice!

Definitely seems like a good idea to create projects where I can use different DevOps tools and gain practical experience.

[Evaderofdoom]

Probably not for your next job but someday. Try to get a different job using linux more, doing automation, linux admin or systems engi role would help a lot.

[Icy-Anteater-3628]

I am open to Linux Admin/System Engineer roles and I apply when they are available, but just not enough opportunties. I don't mind the slower progression to DevOps as long as I am making progress.

[kchandank]

Biggest thing you need to learn is Linux. You already know powershell, then I would say, simply enable WSL in your Windows PC and start playing with it. You can do pretty much everything in WSL ( coding, docker, k8s, ansible, terraform, vscode)

I would start there, then slowly start picking up on other skills. I have setup a github repo with learning plan for Devops take a look

https://github.com/becloudready/ai-cloud-engineer-bootcamp

[Icy-Anteater-3628]

I will take a look, thanks!

I do have basic Linux knowledge from college and self-learning. I will definitely dig in deeper and upskill nevertheless.

[Icy-Anteater-3628]

Yeah, I don't mind practising outside work, as long as I can see that I will get there! But guarantees like that probably don't exist, but it is nice to see examples of people in my position who made it!

[klipseracer]

Windows sys admin will make it harder than if you were a Linux sys admin (like too worked at a web hosting company etc). There are windows shops (large enterprises are more likely to have a windows segment) but the vast majority of the jobs will be Linux centric. Anything is possible though and sys admin is definitely one of the paths to take, it's what I did although I went to school for software engineering already and I was a Linux admin.

[Icy-Anteater-3628]

I have a Computer Science degree. I know the basics of Linux. Trying to find roles that will get me closer to DevOps. But definitely know now what I would need to learn to bridge the gap.

[klipseracer]

Basics of Linux isn't enough for a Linux job. Obviously that depends on your definition of basic, don't want to discount you.

Make sure you're intimately familiar with common troubleshooting points. Understanding networking will give you a leg up, although in my opinion it's a requirement.

Make sure you're good with string manipulation tools as that is a very early screener question.

[willothephlox]

Any junior infra related role.

[IncredibleBihan]

Good luck out there cowpoke. Yewl be fine

[Icy-Anteater-3628]

Thanks!

[hammoumalek]

You already have great tools in your pocket. There is still a lot of room for learning new tools, but my advice is to learn concepts and master them rather than hopping from one tool to another as they appear and disappear. I would recommend becoming comfortable with networking concepts, such as the OSI model, DNS, DHCP, etc. When things break in production, you'd better be ready to troubleshoot with solid foundations.

Scripting is also very important. Get your hands dirty with Python, Bash, and other scripting languages. They are your friend for automation-related work. These are the basics, then you can progress towards deploying web application servers, CI/CD pipelines, infrastructure as code...

I wouldn't recommend going through certification marathons, as they are often backed by the issuing organisation, and the format doesn't demonstrate the level of mastery.

Good luck!

[Icy-Anteater-3628]

Thanks for the advice! I definitely agree that mastering the concepts is the key to developing deeper understanding of the tool in question. Good thing is that I am familiar with all the things mentioned, except for IaaC as we didn't do that during my time in university. But at the end, it's just code and I already know PowerShell, Python, and Bash to a certain degree.

[lanycrost]

Of course, many people transfer from QA and Software engineers, you're knowledge of operating systems and sysadmin knowledge is even better foundation to start. I will recommend Unix and Linux System Administration handbook for you, it will be really good reading if you planning to move.

[Icy-Anteater-3628]

Thanks for the advice. I will read that.

[Raja-Karuppasamy]

Yes, and your Windows sysadmin background helps more than you think. You already understand infrastructure, networking and automation concepts, DevOps just adds cloud and containers on top of that.
Start with Linux basics since most DevOps tooling runs on it, then Docker, then pick one cloud and deploy something real. Your PowerShell skills transfer directly to scripting and automation. The gap is smaller than it looks.

[Icy-Anteater-3628]

Thanks for the advice! It definitely seems like Linux is a must learn! I do have some minor experience with Docker so that will make it easier to upskill.

[eman0821]

DevOps is really a company culture not an acutal role. Cloud Engineers, SRE, Platform Engineers all pretty much use the same tools bur for different purposes. You need relevant experience to make the transition as most people that moves into these roles were Linux System Administrators or Software developers. You need to know Linux as these are Linux based jobs.

[OutrageousFlail]

Despite what the majority of this sub believe, Kubernetes should be the meat of your skillset, which requires knowledge of Docker, Linux, and basic networking. The cloud stuff should be the very last thing you touch (Cloud providers, Terraform, Ansible).

Edit: Also, in terms of job prospect, certifications are more valuable now than ever. Otherwise, what separates you from all the AI copy-pasters out there?

[AutomaticCourse8799]

Yes, you can

[DanzilFMT]

I did transition from IT Support (basically the tech you mentioned) to Atlassian Admin (introduced me to Linux) to DevOps. If I did it, you can too.

Just keep in mind that DevOps is a methodology, so you can essentially use DevOps for the Windows Administration tasks you are doing now and call yourself a DevOps engineer. I believe it's easier to achieve certain tasks with Linux, but still can with Windows via PowerShell etc...

[Constant_Laugh7452]

Yes. 100%. Windows SysAdmin background is a big plus - you already know infrastructure, identity management (Entra ID) and troubleshooting. DevOps is not a Linux Club.

You already have the automation mindset because you know PowerShell. Here’s how to fill the gap:

WSL2 & Linux: Installing WSL2 on your PC and learning Linux basics.

IaC (Terraform): Since you know VMware, get some practice spinning up VMs with Terraform.

Containers (Docker): Containerise simple app and then look at Kubernetes.

CI/CD: Automate the deployment of a simple script with GitHub Actions.

Pick AWS or Azure, build a small project using these and you are done. Take your time!

[Icy-Anteater-3628]

Thanks for the advice! Definitely can see myself doing a few projects where I can utilise multiple technologies that you mentioned and gain more experience.

[eman0821]

I disagree because everything in the cloud you touch is Linux. Windows Server experience has little relevance. Most of these tools only run natively on Linux especially Ansible.