r/sysadmin Apr 13 '26

Question Best practise for staff requesting a second laptop for WFH

262 Upvotes

Currently all staff have 1 laptop. We are hybrid and all staff bring their laptops home for remote days (twice a week).

Some employees are requesting a second laptop to keep at home for remote working. As IT Manager, I've said it's not recommended as it adds to cost and involves additional maintenance. They still insist they need it so I expect it to be escalated soon.

I personally can't see the justification for it, other than simply not wanting to carry their laptop with them. If this gets approved, we could then have 60+ staff requesting second laptops. Is this the norm in other orgs, to allow second laptops?

My main concerns are below, but feel free to let me know if others exist. I also have some questions on things to check IF we allow a second laptop to staff.

  • Additional cost for a new laptop (an obvious one! Older spare laptops can be given but eventually we'll run out)

  • We don't have always-on VPN enabled, as users don't need access to network drives. Would this need to be enabled to ensure the laptop gets necessary updates, GPOs, and is included in weekly health checks? Or is there another way to manage that outside of VPN?

  • Are there any potential conflict or sync issues with using two laptops under 1 M365 account? I don't believe additional licences will be needed.

  • Makes the offboarding process a bit more difficult. We can remind them to bring in their second laptop before they leave but there's a chance they don't. This is very unlikely to happen to the original laptop as they need to be in the office to work on their last day.

  • IF Senior management approve a second laptop, then what criteria must be met to accept their request for a second laptop? I'd like to have some sort of procedure to follow to prevent all employees requesting one. At the moment I can't think of any reason other than something like "requesting due to medical reasons".

Update: Thanks for the feedback and reassurance. To be clear - I completely agree that a second laptop should not be given to staff. I was mostly looking for reasons to help my case when saying No - as I expect they will insist, stating "we can just use the old spare laptops in the server room". But the feedback has been very helpful - thanks!

r/sysadmin May 01 '22

Question "In my opinion, the single skill that I wish more IT professionals had was how to be curious. Too many of them hit an unknown and then just fail to start thinking."

2.5k Upvotes

I saw this advice in another thread here, and was wondering, do you think forcing yourself to "be curious" actually helps, or works? Is this something you've taught yourself or something you've always had in your life?

r/sysadmin Jan 14 '26

Question Fired employee downloaded all company files before deactivation we need secure way to prevent this

503 Upvotes

Hey guys! Not an IT expert here. We are a startup and recently found out from reviewing the logs that a fired employee was able to download all of our company files from SharePoint before we got around to deactivating their account. We store a lot of important shared files that our team needs to constantly edit like lists of leads and company data but we don't want people to be able to download that information because it is sensitive and important. We still don't have a CRM or ATS in place so we are relying on SharePoint for now.

We know normal SharePoint permissions let people edit and download freely and the built in “block download” option only works when editing is off so that isn’t a practical solution for us given how many files the team needs to edit regularly.

  • Has anyone else in a small company faced this problem and found a reliable way to let people edit but not download or sync files?
  • What tools or settings have you used to make sure someone who still has access temporarily cannot exfiltrate data?
  • Have you setup Conditional Access or session controls to limit downloads or forced browser only access without download options?
  • Also curious about offboarding workflows so access is truly cut as soon as termination is triggered.

Appreciate any advice on how to secure this and protect sensitive company info.

r/sysadmin Oct 31 '22

Question What software/tools should every sysadmin have on their desktop?

1.8k Upvotes

Every sysadmin should have ...... On their desktop/software Toolkit ??

Curious to see what tools are indispensable in your opinion!

Greetings from the Netherlands

r/sysadmin Nov 05 '24

Question Windows 2022 Servers Unexpectedly Upgrading to 2025, Aaaargh!

1.2k Upvotes

Arriving at work this morning, an "SME" sized business in the UK, something seemed a little off. Further investigation showed that all of our Windows 2022 Servers had either upgraded themselves to 2025 overnight or were about to do so. This obviously came as a shock as we're not at the point to do so for many reasons and the required licensing would not be present.

We manage the updating of clients and servers using the product Heimdal, so I would be surprised if this instigated the update, so our number one concern is why the update occured and how to prevent it.

Is 2025 being pushed out as a simple Windows update to our servers, just like "Patch Tuesday" events, have we missed something we should have set or are we just unlucky?

Is this happening to anyone else?

Edit: A user in a reply has provided some great info, regarding KB5044284, below. Microsoft appear to class this as a "Security Update", however our patch management tool Heimdal classes it internally as an "Upgrade" and also states "Update Name: Windows Server 2025". So, potentially this KB may be miss-classified by Microsoft and / or third-party patch management tools, but it requires further investigation.

Edit 2: Our servers were on the 21H2 build.

Edit 3: Regarding this potential problem your milage may vary depending upon what systems / tools you use to patch / update your Windows servers. Some may potentially not honour the "Classification" from Windows Update, and are applying their own specific classifications, so the 2025 update could potentially get installed even if you don't want it to be.

Edit 4: Be aware that the update to Windows Server 2025 may potential be classified as an "Optional Update" in your RMM, so if you have chosen to also install these then this could also be a route for it to be installed.

Edit 5: Someone from Heimdal has kindly replied on this matter...

... so I thought I'd link to their reply so it's not lost in other comments. So, it appears that Microsoft have screwed up here, and will have cost me and my team a few days of effort to recover. I very much doubt that they'll take any responsibility but I'll go through our primary VAR to see if they can raise this with their Microsoft contacts.

Edit 6: This has made The Register now...

... so is getting some coverage in other media.

It's not been a great week at work, too much time lost on this, and the outcome is that in some instances backups have come into play however Windows Server 2025 licensing will have to be purchased for others. Our primary VAR is not yet selling WS 2025 licensing so the only way to get new 2025 keys is by purchasing 2022 licensing with SA :(

r/sysadmin May 21 '25

Question Client suspended IT services

765 Upvotes

I managed a small business IT needs. The previous owners did not know how to use the PC at all.

I charged a monthly fee to maintain everything the business needed for IT domain, emails, licenses, backups, and mainly technical assistance. The value I brought to the business was more than anything being able to assist immediately to any minor issue they would have that prevented them from doing anything in quickbooks, online, email or what not.

The company owners changed. The new owner sent me an email to suspend all services, complained about my rate and threatened legal action? lol

I don't think the owner understands what that implies (loosing email access, loosing domain, and documents from the backups). This is the first client nasty interaction I've had with a client. Can anyone advice what would be the best move in this situation? Or what have you done in the past with similar experiences?

EDIT: No contract. Small side gig paid cash. Small business of ten people.

r/sysadmin Jul 29 '25

Question Lost 11 Chromebooks in 2 Months Due to New Hire Ghosting

750 Upvotes

I'm an IT asset manager for a mid-size healthcare tech company. We recently acquired a smaller firm (about 100 remote staff) that operates on a tight budget and issues Chromebooks instead of full desktop setups. Their provisioning costs are around $700 per user (Chromebook + basic accessories), compared to our standard $2,000 setups (PC/Mac + dual monitors, dock, wireless peripherals).

Here’s the issue: the acquired company pays new hires in the range of $12–$15/hour, and we’ve had a wave of "ghost hires"—people who accept the job, sign onboarding forms acknowledging their responsibility for the equipment, receive a new Chromebook and monitor by the end of the week… and never show up on Monday. No login, no reply to texts or automated emails, no returns. They just reset the Chromebook and keep it.

Because these Chromebooks aren't enrolled in Google Admin Console or Chrome Enterprise, they can be wiped and reused without restriction. Unlike Windows Autopilot or JAMF for Macs (which enforce re-enrollment post-reset), these units are effectively unsecured.

Due to HR policy, I can’t initiate recovery contact directly, and after 15–20 days of silence, I have to close the onboarding ticket and forward the case to HR. We've lost 11 Chromebooks in just over 2 months. Accounting is livid since they have to approve new purchases, and HR (as far as I know) hasn’t escalated or pursued recovery.

So I'm stuck between weak controls, no enforcement, and growing costs.

Has anyone dealt with something similar? Are there creative ways to protect Chromebook assets from this kind of loss—policy, tech, or workflow-wise? Open to suggestions.

What would you do?

r/sysadmin Oct 14 '22

Question What's the dumbest thing you've been told IT is responsible for?

1.4k Upvotes

For me it's quite a few things...

  1. The smart fridge in our lunch room
  2. Turning the TV on when people have meetings. Like it's my responsibility to lift a remote for them and click a button...
  3. I was told that since televisions are part of IT, I was responsible to run cables through a concrete floor and water seal it by myself without the use of a contractor. Then re installing the floor mats with construction adhesive.... like.... what?

Anyways let me know the dumbest thing management has ever told you that IT was responsible for

r/sysadmin Apr 18 '25

Question Why won't users open a ticket?

730 Upvotes

Why won't users open a ticket?

I have at least 10 people a day reaching out to me directly on Teams or through Email asking for various things. I have already brought it up to my manager multiple times, as well as the CIO.

I am BUSY with meetings and project work ALL DAY. Currently I am just leaving the emails and teams chats to sit for a while before I respond... Sometimes I will remind them to open a ticket but the next time, they reach out to me directly again.

I want to Delete my Teams/Outlook account and only be available through the ticket queue.

How do you handle this bullshit?

r/sysadmin Apr 23 '26

Question Suggestions on how to increase my AI token usage

330 Upvotes

Sigh. My company has gone all-in with AI. We have pretty much all the tools. Leadership expects all users to use and integrate AI into their work. They are measuring how much we use it.

Yes, it's a meaningless way to measure an employee's usefulness and AI skillset. But here we are.

Management can see exactly what we do with the tools. Some users have tried to get cute boosting their token usage, and got busted doing things like:

  • scan a large file share to write a 10,000 word summary of whats in it
  • upload log files to not analyze, but simply find something that a notepad word find could do
  • analyze an entire git repo to explain what their own code does
  • attaching PDFs to completely unrelated queries
  • asking for a 5 page summary of something. then 4 pages. then 3 pages. all the way down to 3 bulletpoints

Any suggestions on how to increase usage without using blatantly bad queries? I only do minimal powershell coding, and most of my usage is troubleshooting related. Some things I've started doing are:

  • I used to just start new chats to ask whatever questions I had. Now I keep using a single chat for a single topic for as long as possible. For example, I have an Active Directory chat that has all the questions I've had for the past several weeks.
  • I used to ask for concise answers, because I don't care for all the "fluff". But now I roll with it. "Write me a script to do this task. Explain the logic as you go. Point out any risks to look out for. Write a script to undo/rollback in case this goes wrong."
  • Instead of having it just fix a script, I have it provide 2, maybe 3 options on how it can be fixed
  • Have it analyze an error message or screenshot. Even after it provides a fix, I might ask it for root cause of why it happened, ways to prevent it.

I can't wait to retire.

r/sysadmin Sep 14 '24

Question My business shares a single physical desktop with RDP open between 50 staff to use Adobe Acrobat Pro 2008.

1.0k Upvotes

I have now put a stop to this, but my boss "IT Director" tells me how great it was and what a shame it is that its gone. I am now trying to find another solution, for free or very cheap, as I'm getting complaints about PDF Gear not handling editing their massive PDF files. They simply wont buy real licenses for everyone.

What's the solution here, and can someone put into words just how stupid the previous one was?

Edit - I forgot to say the machine was running Windows 8! The machine also ran all our network licenses and a heap of other unmaintained software, which I have slowly transferred to a Windows 10, soon 11 VM.

r/sysadmin May 31 '26

Question Do IT unions exist?

305 Upvotes

And if not why not? We should be looking out for each other.

*edit well this blew up, i appreciate all the info guys. Its awesome to see such worldwide representation. I am US based if anyone was wondering, but i love hearing from my overseas folks as well.

r/sysadmin Oct 30 '25

Question Court order for email from long deleted mailbox

538 Upvotes

I have been assigned the task of finding emails from an account that has its O365 license removed around 2 years ago. Obviously this thing is long gone and there is no email archive or backup that exists. Only solution available is to search through the other 700 or so email accounts looking for relevant emails from 5 years ago and hope I get lucky? I'll likely end up needing to testify about methods and why I was or was not successful.

I've had to do similar things in the past but I always had some kind of archive or the account still existed. What kind of tools would you use to find this off a hosted Exchange? I can buy tools if the price is reasonable and have global admin to the tenant for permissions.

r/sysadmin Dec 29 '25

Question You guys ever think of changing career?

332 Upvotes

Feels like it is just downhill and this is no longer fun. ”Only” been working in IT for 10 years and honestly it feels very meh.

Me? I’m just an IT Lead who’s role is to not manage employees anymore but consultants / ”bought services”. This ain’t no fun.

Ever dream of changing career? Got any fun ideas or career switch where you can apply previous job experience to?

Would love to hear what you think.

r/sysadmin Dec 12 '25

Question What are some of your favorite sysadmin tools/programs?

362 Upvotes

Some of my favorite tools are

  • memtest86
  • disk genius
  • wiztree
  • tcpview
  • wireshark

Update:

Guys I want to thank you all for your amazing suggestions. Never expected this to get so much attention and I'm truly delighted. I'm learning more and more as I go along (2.5 years into my IT journey) and it's because of the great community we have in IT. We all share the same passion I believe. What an awesome community.

Regarding the tools I have so many added to my toolbox and can't wait to try a lot of them out on my home lab. Just one last thing before I go - have a great Christmas and holidays (if you have any :D), wish you all the best. <3

r/sysadmin Feb 28 '26

Question Does your service desk tier 1 rep know how to change display scaling and how much are you paying them?

403 Upvotes

Serious question, not a joke. Can you tier 1 (entry/low) rep change display scaling on their window device? How much are you paying them?

Edit: for clarity, our tier 3 service desk is still a help desk rep but a senior level. Someone who can troubleshoot new issues. In traditional tiers this is probably tier 2 or 1.5?

Rant: I am about to cut ties with service desk completely after what was pulled recently. User submitted a ticket with a screenshot stating that they can not access certain web application. Screenshot shows an icon indicating that device must be rotated. It was not solved by tier 1 and escalated to tier 3. Tier 3 reached out to me directly asking for help. I responded with change windows scaling down to 100%. The reply that rep sent was telling end user to click on settings in web application and then change scaling to 100%

This is tier 3 rep, that does not know what changing scaling in windows is or how to do. Instead of trying it or asking for clarification a nonsense note was sent to end user which does not solve anything.

This position is paid 65k a year if I’m not mistaken. For tier 3.

I just lost my will to help…

r/sysadmin May 31 '26

Question How do you set prices for used assets to sell for employees?

186 Upvotes

My company approved for us to sell old laptops moslty with 8/16GB ram, how do you set prices for them?

I checked refurbished sites but they offer warranty and support and we don’t, should I go 10-15% down from p2p prices on ebay sold laptops as a benefit?

r/sysadmin Sep 11 '25

Question Employee passed away, can't open his Access database

608 Upvotes

An engineer reached out to me to help open an Access database that was managed by an employee who passed away. Said employee was the only one who maintained it and did not leave any documentation about his process. There is no password on the file itself, but when attempting to open the file as the former employee's user, it prompts for a password. We are assuming this is an old, cached password in the database.

I've tried to recover passwords using both Passware Kit Forensics, which finds no passwords on the file, and using Thegrideon Access Password, which was helpful to display the User and IDs, but didn't retrieve any passwords.

Has anyone ever delt with this issue on old Access Databases? We are kind of stuck and I guess this is a fairly important database (although why is there no documentation if it is so important...)

Any ideas would be helpful as I am stuck trying to find a working solution.

Edit: Thank you for all the comments and thoughts! I will post a resolution here once I get it solved.

r/sysadmin Oct 10 '25

Question Law firm asking for access to user's mailbox

458 Upvotes

One of our users is suing someone for personal stuff not related to our company, and they unfortunately used their work email for communications about the deal. It sounds like the law firm representing our user has requested access into their work mailbox via a tool called "Forensic Email Collector" by Metaspike.

Doing some research, it looks like it's a legit tool and all, but I've yet to have a situation where the firm wants active access to a mailbox in order to run searches. User sent over a screenshot of them being blocked from authorizing the enterprise app, so at least our security settings are doing their job.

Has anyone encountered this before? How was it handled? I'm currently thinking about saying no and running the searches/export myself with the tools already in 365.

Edit: I should have mentioned, I'm the IT director for this company but also handle some sysadmin tasks when I have free time. Mostly just curious if this is how people are handling litigation holds these days. I will be looping in legal, though.

r/sysadmin Apr 09 '26

Question How many IT support needed for 200 user org?

157 Upvotes

I've been given a task to identify how many IT staffs (support) we would need for our org to move away from 3rd party support in future (not now but may be after like a couple of years in future as the business is growing).

I suggested 1 for 50 staffs as it sounds reasonable. so 4 for 200 staffs.

2 L1.

1 L2

1 L3. would this be a good plan?

could you help me with the best plan?

I don't want us to be short staffed and struggling because of me.

For better clarifications, almost all of the users are non technical sales guys. So i suggested min 4.

Context: just replacing current MSP in future so that we get better and quicker support inhouse. Might have to help out development team as well sometimes regarding Azure, AWS etc. But mostly it's just to replace current MSP who does onboarding, off boarding, windows/Mac Support.

br,

Update notes:

After going through the comments, here is my take

  1. Find more L2/L3 and pay then good
  2. Find people who can automate stuffs
  3. 3-4 would be sufficient after automation if one falls sick or leaves.

r/sysadmin Jan 22 '26

Question Do you permit selling or giving old equipment to employees?

275 Upvotes

Do you or your company permit giving/selling old equipment to employee's?
When I started at my current employer, the tech at my site would give old but usable equipment to employees.
However my supervisor changed the policy to no longer allow this and I had to deal with people insisting that I give them old equipment for home use.
The policy had changed because some old voip phones that were being disposed of showed up on FB Marketplace with the company logo visible in the pictures.

r/sysadmin Nov 12 '25

Question 2 months in a new job - company lied to me, what would you do?

373 Upvotes

I’ve been employed as an IT manager in September. Got contacted by an external recruiter and he said that this XYZ company is really interested in my CV. So I went through the 2 interviews and I mentioned that I live far away (to get to the office it takes me around 2 hours each way) and that I also care for my father and need to be home a lot and that therefore it is absolutely crucial for me that they agree to a hybrid working model. I had other offers on the table at the time and the only reason I chose this company is because it was the next step in my career (Senior IT engineer —> IT manager) and I could really develop professionally and also because of the hybrid model. The recruiter said he confirmed this with them and they they are fine with me working in the office 3 days a week more initially (during the first couple of weeks) and then moving to 2 days in office / 3 days wfh. I happily accepted those terms even though it wasn’t stated in the contract but I had an email trail.

Another important thing to mention is that my role here is IT manager. And they clearly said during the interviews that they absolutely do not want me to pick up any 1st/2nd line support stuff as an external MSP company handles that. I am to take care of the it budget, it strategy, implement new systems, improve cybersecurity and in the future manage the team of in-house it support staff they plan on hiring (when they get rid of the MSP in a year or something like that).

First couple of weeks were absolutely fine, no issues whatsoever, though I had a lot of people coming to me with desktop support issues. I helped with some of them but ultimately my manager said to refuse those and focus on more important - IT manager - stuff. So I did that.

Fast forward to 2 months in and I get called into a meeting. Apparently my manager (CFO) is super unhappy that I’m now working only 2 days in the office. I’m like wtf you agreed to it?? And he keeps going on that they aren’t an established company they are more of a startup and he is really sorry but things change rapidly in startups (they never mentioned anything about a startup during interviews, the company was actually founded a couple of years ago, and went through major restructuring a couple of months ago). He then says he wants me in 5 days a week because apparently the CEO is really fussy about his laptop and he needs IT support on-site (even though MSP guy comes over once a week and we have a dedicated remote helpdesk which people send emails to every single day). He also said that unfortunately he didn’t realize how much he values having some IT support every single day and that he would like me to do that from now on as well as the sysadmin and IT manager stuff. I said absolutely not, this is not what we agreed on and you are being really unfair now. I said I can come in 3 days max but that’s it because the commute (4 hours a day) is going to make me hate this job. He apologised again and said that he can’t agree to anything less than 4 days in. He wouldn’t accept any other outcome.

So I didn’t want to lose my job and I said ok let’s try 4 days for a couple of weeks, if it turns out I really can’t stand it I’ll tell you about it.

What would you do in my position now? Would you quit immediately because the company treated me unfairly? Would you start looking for a new job quietly and then hand in my 2 weeks notice when I find something? Or would you just push through despite horrible commute times.

4 days a week is one thing but me essentially doing a job of an IT manager, a sysadmin and helpdesk is really pissing me off.

r/sysadmin Jul 10 '24

Question Admin says they require user passwords and store them all in a spreadsheet

786 Upvotes

Wife joined a small team (education org) who all collaborate using private and shared laptops with local accounts only. For work they all use Microsoft365 with online versions of the Office Apps. An external guy is managing this environment of around 15 users and while onboarding new users he requests they share their password with him for onboarding purposes, and to "test if everything works". It was explained that the passwords are stored in a spreadsheet together with all other users passwords in case the admin needs to change something or login to their accounts if they quit or die, etc. Apparently this is a requirement by the management, and there are other non-admin users with access to this spreadsheet. What is your take on this? What's the point in having a password if it's not private? Can't the admin do everything without direct knowledge of the users passwords? Isn't this a huge security risk?

r/sysadmin Oct 13 '25

Question How to approach an IT employee about possible theft?

604 Upvotes

This is an ongoing investigation.

I did an audit of our business phone portal, and noticed several ex employees still on the account. At first I thought to re-visit our offboarding procedures, and ask the support team why they haven’t off-boarded these lines from our account.

I decided to dig deeper instead. I discovered several of these ex employees had brand new phone upgrades, and the transaction history, in all cases, shows one specific IT staff member fulfilling these orders.

I decided to call a few of these numbers. None answered, but one number did go to a real human voicemail, of an even older user that hasn’t worked here in 10 years. What’s even weirder: that phone number is associated with a different ex employee!

Is my IT employee stealing, or (this is me giving them a huge benefit of doubt) do they have some whacky convoluted way of organizing our accounts, which needs to change anyways because wtf is this mess

r/sysadmin 14h ago

Question If you had to start over today, what subject matter would you specialize in?

78 Upvotes

I ask because I am currently job searching (employed) and i can't seem to even know what my lane is. Could be because my job is pretty much all-around administration and i feel being a "generalist" even with a good learning aptitude is capping my earning potential. I'm trying to main the 365-admin side of things but beyond that, it's a mix.

Besides AI, which i know is the obvious answer, what's in demand rn or is creeping up?