Helpdesk to Sysadmin — looking for honest advice from people who've made the jump

Posted by Throttle8996@reddit | sysadmin | View on Reddit | 17 comments

Hi everyone,

I'm a helpdesk tech in Canada with about 3 years of experience split between an MSP and retail IT. Day-to-day I've handled ticket queues, user provisioning in Active Directory and Entra ID, basic M365 troubleshooting (Exchange, SharePoint, OneDrive), and some networking like DNS, DHCP, and Wi-Fi issues. On the field side I've done workstation imaging, cabling, and physical security installs.

I have an ITIL 4 Foundation cert. My A+ has lapsed and I haven't done much scripting — I know that's likely a gap.

I want to move into a System Administrator role but I'm being realistic: most of my experience is reactive support, not owning infrastructure. I'm trying to figure out what I actually need to bridge that gap rather than just applying and hoping.

What skills or certs made the biggest difference when you (or someone you hired) moved from helpdesk to sysadmin?
How big of a red flag is limited scripting experience, and what's the fastest realistic way to address it?
I've heard home lab projects help — which ones have the most impact, and how should I document them to show value on a resume?
How do you get a sysadmin job without sysadmin experience on your resume — what did your first role actually look like?
What does a junior sysadmin's first 6 months actually look like — are you still doing helpdesk tasks or do you get real infrastructure ownership early on?

For context, I'm currently between roles and actively job searching, so any advice on what to prioritize first would be especially helpful. Open to honest feedback, including if you think I'm not ready yet and what I should do about it. Thanks.

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cakeBoss9000@reddit

I know this is pretty standard advise but I cannot overstate how beneficial having a homelab is at this state of your career. You mention you don’t “owe” any infra. Set up your own infra!

You don’t need much to get started: A few raspberry pi’s or mini PCs and a small network switch. 1. Start by setting up a hypervisor in these machines, proxmox is free and it’s picking up a lot of traction in the industry since VMWare was brought out by Broadcom. Learn how to create VMs, backups, etc. 2. Set up a firewall: use opnsense or pfsense. This firewall should be used to allow things in different vlans in your network to talk to each other. All communication should be denied by default. Only allow specific endpoints to talk to each other. You can also set up a VPN server so you can access your infra while away from home. 3. Set up an identity provider: if you hate yourself I guess you could create a windows server VM and set up an active directory. I personally prefer using something more modern: keycloak or Athentik are good, lightweight options you can easily set up. The idea is that your users you create here can access your apps in your homelab. My personal user in Authentik has access to proxmox, pfsense, gitlab and more apps… this eliminates needing to create users in each app and is actually considered more secure since you can (and should) set up MFA for the SSO. 4. Basic Linux + Docker. You need basic Linux to work with docker. If you’re not too familiar with it, you now have a hypervisor which allows you to set up linux VMs and fool around. Docker allows you set up services in a standardized way. I can get an app that I didn’t even know existed up and running and servicing users in a matter of minutes just by briefly reading the DockerHub docs. 5. Set up (useful) services. Your homelab should be treated like a corporate environment: it should add value beyond just being and IT environment for the sake of being an IT environment. There are a ton of cool projects you could set up (specially knowing docker) - NextCloud for storing your photos and sync your phone with them - jellyfin for streaming your legally purchased tv shows and movies - Actual Budget for managing your finances - Home assistant for managing your smart devices within your house (think anything IoT, this deserves it own vlan in your network btw) 6. Learn automation tools. So far you’ve built everything by hand. This is the “base” but if you really wanna step your game up, you need to learn tools to aid with deployments and systems administration. Think Ansible or terraform. These are NOT programing languages. They are fairly easy to start to use but difficult to master. 7. Version Control. You need to learn git. You can learn the basic commands in an hour. 5 git commands will allow you to do 99% of what you’ll ever need. Having your terraform or ansible in git repos will not only backup your code but also open the door for the next step. 8. Continuous delivery. You are now stepping into the realm of DevOps. You’d want to set up a service like Jenkins or GitLab. If your hardware is limited I’d say to go with Jenkins and store your code in GitHub. The idea is to set up a system that will automatically changes in terraform or ansible whenever you deploy code on a specific branch on git. There’s a lot of debate and different strategies about how to do all of this. Keep it very simple. One git repository per app.

You could realistically learn how to do all of this in perhaps… a few months. All depending on how much time and effort you put into it. Regardless of what anybody in this sub says, AI is your friend. Use it to get started and ask questions when you get stuck.

Document your journey and put it out there somehow. Throw all of it on GitHub. If I saw anyone doing all of this I would have no problem hiring them as a sysadmin.

sudo_rmtackrf@reddit

Hey mate, im one a few who got a admin job with out experience or help desk.

What i did was look at job ads and see what skills they are looking for. I set up VMs and practice what skills I sawcin ads. I'll break things, fix it. I'll take notes etc.

On my resume cover letter ill put down no commercial experience but say what I did in my virtual machines. Like patching etc. Ill taught my self basic scripting to automate some things and out that in my resume. In the interviews I mentioned my cover letter stated but said if I was to do for you ill do this, this and that.

My first boss love it and hire me as I show potential.

Now im a linux dev ops engineer on over 200k a year and can code in 3 languages. I still havnt got formal training or certs. Just experience on my side now.

Constant-K@reddit

I made the jump from help desk to sys admin around 2015 entirely by learning PowerShell scripting. As a hiring manager today, that is no longer enough. I expect candidates to have some familiarity with the Graph API too.

Help desk are generalists responsible for break/fix at the user level. If you’re serious about advancement, you need to be able to manage requests and incidents at scale. Sys admins support the org.

I rely on my administrators to manage dynamic security and distribution groups, identity management, transport rules, MDM policies, reporting, post-mortems, and org-wide changes as directed. If you can reliably demonstrate these qualities, and your company has the budget and need, a promotion will happen.

kachubey@reddit

I did all this as an IT Specialist, but now I can't find a job

I'm sorry to hear that. I don't want to make any assumptions, but selling yourself is equally as important as your experience and skillset.

littlebearz@reddit

Helpdesk -> Junior Linux System Admin by learning RHEL and linux, basic scripting in bash (nowdays much easier with AI) Then with any sort of Cloud Cert (AWS).

Fastest way I'd say is try automating your reactive support, example: using python script to read your inbox for new message and then action those email into action by subject keywords + from.

First 6 month is basically learning the ropes in 1 week or less by shadowing others , then taking on small project and customer work and ramp up as you get familiar with the environment.

I took on 2 project within the first 6 mth, first wrote a customer support ticketing system from SMS shortcode, back you can text 21212 and it goes to twitter.

The 2nd project was when app crashes etc, it will output a link to stackoverflow with ?query=$error_message

apples_r_4_weak@reddit

Act like you know how server works until they gave you access to it.

I remember taking ownership of some old Linux with very old attendance system and a wsus since no one wants it to the point that they entrusted it to me. I learned a few things and add it to my resume.

As help desk, learn the basics of account CRUD.

Certs help

RansomStark78@reddit

My aws saa has lapsed, i couldnt care less

Dumpster fire in it atm

Look at jobs in your area, pick key skills and focus linux admin always a win

przemekkuczynski@reddit

Helpdesk --> sysadmin. I worked on-site as 1 person with 3rd party . In free time I took party in different forums about Microsoft solutions, online/local meetings Microsoft enjoyers, prepare and took MS exams especially as chapter Member. This give me knowledge that my boss see and I became sysadmin

xVenlarsSx@reddit

For me it was asking question, being interested and being able to change perspective. You have to look at the bigger picture when doing sysadm work, and that can be hard when you are in the ticket trenches. Be interested, show initiative, and ask questions.

Your best path right now is to look for ways to prevent future issues from happening, and documenting that. Show your work and what is gained from it. If it's out of scope, be open about being interested in that project long term.

A homelab can be a lot of things, but nobody will take it seriously on your resume. What they will care about is your knowledge of systems and tools, that you honed in your lab.

You build a lab to experiment and learn about stuff hands on, like backups, managing VM deployment, storage, advanced networking. You build things you want to work on, and then you break it, ans repair it or rebuild it. It won't add a line on your resume, but when you get a technical interview you will know how to answer, from experience.

Also, you should build a lab because you are passionnate about tech and don't mind doing it at home too. It's not for everyone, and burnout can be real. So focus on projects that interest you, and you will never lack motivation.

You also have to realise that not every workplace will give you mobility, even if they promise it.

Be open to opportunity outside, and never stop applying. I got a job asking for 5+ years of experience in system ownership with just 2 years of helpdesk, cus I was direct, transparent about what I had to cover for, and hungry for the opportunity. I was lucky, and the job market can be hard, but you gotta make your own luck too.

Best of luck!

SuboptimalSupport@reddit

I made the jump from helpdesk to what was supposed to be a junior "get taught the ropes" sysadmin role with a mac focus at the same place, and instead got a two week crash course before getting launched into the deep end on my own as the windows guy. Fun times.

Going from troubleshooting endpoints to managing the backend wasn't too bad; a little bit of poking around, and a few generic "here's how this tool works" videos bridged the "Keep things from falling apart" stage long enough to get familiar and really learn by doing.

Scripting is definitely the skill I wish I'd already had. Lot of scripting to do, and at least for me, the early scripts are barely functional, so in addition to figuring out what my predecessors where thinking (as is tradition), I was also constantly having to go back and figure out what I was thinking, too.

Another good skill to have, that isn't always built up as a helpdesker is documentation. Detailed, navigatable, and commented with thought processes. It's usually billed as "good for continuity" but it really helps you as much as anyone; keeps your processes organized, gives you a reference to pull from for similar future projects, and helps you work through challenges and develop your skills if you're also including comments on intention and thought process.

And as always, you gotta be curious. "Why...?" will bring you no end of pain and suffering, but it will also avoid so, so much more.

andecase@reddit

Our Junior admins basically operate as half Tier 2 help desk half admin. They do escalations, smaller implementations, app maintenance, scripting, and fill in for tier 1 when needed. We generally start you off heavier on the help desk side while you learn the environment and give you some less disruptive admin tasks. Depending when your how you handle things we will give you bigger tasks as time goes on. A lot of times we will give ownership of services like, cameras, printers, mdm. Things that aren't as critical when mistakes happen, and have more breathing room for you to learn.

For things to learn, the obvious basic windows and Linux server admin stuff CLI, network configuration, storage management, logs, etc.

Get familiar with a few hypervisors or just virtualization in general even if it's just theoretical via reading docs, or courses. I recommend proxmox, hyper-v, or VMware. Also, containers, you will eventually have to learn them. Start with docker or podman, if you feel adventurous learn kunernetes. Some cloud is always good as well.

Networking is an oft forgotten skill in my experience. Make sure you are familiar with vlans, routing, and the common protocols.

As for scripting, for us it's not a deal breaker, but it definitely is high on the list. Do Powershell in a month of lunches, whatever the bash equivalent is, maybe some python.

Most importantly in my opinion, work on your troubleshooting skills. The second most common reason we pass on people in interviews is their troubleshooting skills are terrible. You need to be comfortable getting into an application or tech you've never seen before and diagnosing issues. Its way easier to teach someone scripting or proxmox than troubleshooting skills.

You don't need to be an expert or even know all of these to get a job. With your current experience, and one or two of them you should be able to get started. My work would higher you as you are.

Also, don't worry about doing specific apps or projects to much. Knowing specifically docker isn't as important as understanding containers in general for example. Look for something that interests you and build it out, within reason build it as if it's a production environment.

MoodZestyclose6813@reddit

Can't you ask to slowly start adding responsibilitys to your position? Like setting up the needed firewall configs, vlans, tunnel ACLs, migrating domain controllers, working on the running hypervisors and docker stacks and so on.

I am or was in a similar situation, I got hired into Helpdesk after working 10 years as QA in a software dev comp and I am working my way into the higher tasks and doing less and less 1st level.

Started off maintenance tasks on running servers and doing switch documentations and things like port forwarding, vlan, firewall changes first month. Started on working different deployment scripts month two, e.g. learning to roll out RMM, Software Installations silently. Month 3 was a lot of exchange stuff, like migrating a existing one into o365 and learning how to control rights with Powershell.

Month 4 was a big first project in which I needed to deploy 5 hardware firewalls, which needed to be preconfigured for the local sites network and be connected via Headscale and some IPSec Tunnels. The Hypervisors on 3 of that locations and some machines running on AWS had to be backuped and restored on a new single Hypervisor with minimal downtime (48h) Which was really close because the transfer of data and restore of backups took a loooooong time for those fileservers and amount of SQL databases. Also, while doing that, UPDs had to be converted to FSLogix and some GPOs had to be rebuild, because of new print servers and some software deployment changes.

At around 6 months in I'm the person doing first troubleshooting If a client side goes down, Hypervisor problems occur, switches act up, doing the nightly maintenance work if needed and I'm send out to customers if specific network installations like switches, medical/security devices are needed on site.

But I'm also still a person fixing printers, word add-ins, SharePoint rights, setting up outlooks and OneDrive (....) :)

This was a hard switch for me and a lot to learn, I also have to work closely together with a co-worker who's more experienced. This new skillset didn't change the money I earn a cent, it's still quite low for the stuff I'm working on but as I still often need a hand it's worth it for me. After 2-3 years I want to hunt for a new full sysadmin position.

allthegoodtimes80@reddit

Take on more than your comfortable with. Do the job people think you can't handle and do it well. Prove yourself.

Pale-Price-7156@reddit

> How do you get a sysadmin job without sysadmin experience on your resume — what did your first role actually look like?

For a help desk to sysadmin transition, i listed my help desk job as a systems analyst role. Very generic. If you have the bullets they are looking for, such as stack specific experience; You will stick out. That's what I did.

For scripting, even though its 10+ years old, month of powershell lunches book is everything you need to know to get started, then focus on stack specific snapins.

Finding projects to automate, then even leveraging AI to help you nail some of these concepts, is a great way to move forward. It forces you to learn it, and you are creating an efficiency for the org.

GullibleDetective@reddit

Scripting can help but isn't strictly necessary. Though it can set you apart

Working my way up the ranks at msp, doing onboardings and setting up servers, Infra whole going from t2 to t3 got me into sysadmin

I've also never left the msp world and do alright for myself and work with datacenters and private cloud now

progenyofeniac@reddit

I got hired into a role at a small org where I was intended to be helpdesk but had room to grow into a sysadmin. Looking at what can be improved and learning from those improving it is a step in the right direction.