So I’ve been working professionally with Linux-based systems for a few years, and while I’m not the expert I would like to be, I have got a pretty good feeling for the way those systems work. You have the bootloader, the initramfs, the boot procedure, systemd, PID 1, you can check the logs, you have all those little things that make the system work. Everything is a file, you have file permissions and selinux contexts, you have networkmanager, systemd units, you have (system) users, some just for some services, it’s all dandy… if I have a problem with a program I can usually debug it, check its logs, and get it to run.
Now for work I suddenly need to do lots of administration of Windows systems, Win11 and server, and troubleshoot deep, weird issues…
And I’ve started reading up on it, trying to use PowerShell as much as I can, but I’m just not getting the same high level overview feeling of understanding of how the system works, of how the parts work together. Or even what parts there are, and what they do.
(Especially within an Azure context.)
Books on Windows tend to be very surface level, just instructions on what menus to click through to get a working configuration.
But what’s going on underneath the hood? What do I do when I get a weird VPN issue? I mean, there’s Get-EventLog to check for things in the logs, but… nothing feels connected.
Do you know what I mean?
(Also, how cumbersome is PowerShell? No proper paging like with less in bash, I mean, you can’t go back a page, not with windows more or that powershell pager command, and you have to type sooo many words… and yeah, everything is an object, and I see how that can be a nice idea, but man, does that force you to select properties of those objects like crazy. Is this really a good thing, once you have it figured out?)
Are there one-to-one equivalents between Windows and Linux distros that could help me understand? Or is there a really good book that spells it all out, that sets me on a path where I can someday debug ANY issue and understand what I am seeing and doing?
…and I mean, where do I even start out debugging and understanding things like Entra ID issues in Windows365 machines, and hybrid Azure domains… the Microsoft help usually just seems to be steps on how to configure the stuff, but not understanding how it works…
Sorry, this is all over the place, but I’m just lost right now 🤷♂️ maybe someone has felt those same things before and has something wise to tell me?
I’m the opposite of this. Windows SME but trying to get into linux
If the OS is a space shuttle then a Linux sysadmin is an engineer while a windows sysadmin is a pilot.
As a powershell first guy its really nice and simple to parse an object for the information you need vs using jq/grep/awk. It’s also much faster.
I find myself struggling to get the information I want out of bash sometimes and use LMM tools to assist me. In powershell it’s sort of similar to jq with stepping into an object to get what I need.
As far as the so many words, there’s lots of short hand that’s not really documented. You can also just use a few letters instead of the whole word. What’s a pain is you can’t combine switches. You have to do-thing -a -b -c instead of do-thing -abc
I think it’s the same as with Linux, solving problems slowly gives you familiarity with the system and you start knowing where to look for things. Generally speaking, Windows is way more centralized than Linux.
Half of the things you listed for Linux are optional (selinux, networkmanager, systemd,…) and different distros (or different programs) use different solutions. I still remember moving from sysV init to systemd or from /var/log to journal, to give a few examples. To this day I can’t stand storing coredumps in the journal, although I understand the rationale behind it. You get the idea.
Same as with Linux, I started Windows admin with NT 4.0 so over time you learn things (and re-learn as needed) as you solve problems. There are sysadmin trainings that go a bit deeper. I like Mark Russinovich and his tools and books, you can look into them but it’s subjective.
I have used all windows versions since xp, and I have used windows systems for 15-20 years, starting from when I was a little kid that couldn’t even read. I am relatively very familiar with the system.
I’ve been using linuxes mostly just for the past 7 years, only 3 of which was on graphical environments, and I think understand linux a lot more. here it’s not the location of the menu that I remember (sure, there’s often not a menu for it) but what do I want to achieve, and which component deals with that. all the while windows is still just a thing to me that I know on the surface, but under that it is all held together by black magic.
someone said that a major reason it’s very hard to understand windows like you do with linux is that it’s intentionally obfuscated. there’s also strange decisions and very strange components, and strange things we just got used to, like why does a troubleshooter or the windows update search take ages to complete while not using the cpu, the disk and not even the network.
I can’t say if it’s intentional or not, but there’s a lot of “don’t ask” in many guides (and even in first level responses here, just telling with button to press but not what happens under the hood).
There’s a bunch of windows internals books from Mark either as main author or co-author, here’s a good place to start: https://learn.microsoft.com/en-us/sysinternals/resources/
It’s \ instead of /
Most stuff you can find answers on YouTube.
Windows key + R to run a command easily. (cmd for example is a bit like terminal.)
Eventvwr.msc is like your syslog I think. Most problems will show up there, even if they’re not problems at all. (common place to send scam targets as it looks scary.)
Services.msc to see what’s running in the background. (like systemctl I think, not sure.)
Task manager - Startup tab to turn off rubbish.
Msconfig as an easy way to see services, hiding Microsoft services, or to select safe mode etc.
Rstrui to bring up system restore - works sometimes if a machine is kaput.
Regedit in rare cases - a chonky place where most app and system settings live.
File sharing - need to share the files through the usual file sharing option, but also need to change folder permissions. If only one is changed, it won’t let you. Also ‘control panel’ network and sharing centre, advanced sharing settings, you can turn off password protected sharing for ease, but Microsoft periodically turns it back on.
Hope that helps a bit. Source: residential IT support for 20 years on Windows / Mac. Debian dabbler.
\ instead of / is really annoying.
I recently had to do a template variable replace is batch, resulting in a JSON config file for another program.
A bunch of paths and stuff. And the variables I was substituting in were also used in batch cmds.
It was a pain figuring out when and where to escape or not-escape backslashes.The worst part is it’s inconsistent! Sometimes it likes / sometimes it needs to be \ and every once in a while it needs to be /
please let me be the first facetious reply to your post. i’d say you should probably find God and start to pray.
if it serves the community, let’s please put all the jokes under here. it’s gonna be a long night
I always enjoyed Mark Russinovich’s the case of the unexplained series:
https://learn.microsoft.com/en-us/sysinternals/resources/webcasts
Another commenter here mentioned Russinovich’s books, which I just started reading, and those webcasts are really fun, thanks a lot! I think he is the guy to follow to properly understand this stuff. Let’s see how far I can get :)
You have the bootloader, the initramfs, the boot procedure, systemd, PID 1, you can check the logs, you have all those little things that make the system work
Windows has pretty much the same concepts. These two books talk about all that in deep:
https://www.microsoftpressstore.com/store/windows-internals-part-2-9780135462409
Also check out this one: https://leanpub.com/perfbook
https://learn.microsoft.com/en-us/credentials/browse/
This might help you but I doubt you’ll ever achieve the understanding you seek from windows. Windows is closed source and the inner workings will be guarded by microsoft. Microsoft seems to be all in on security through obscurity.
So short of getting a job a microsoft and gaining access to the source code I doubt there is anywhere that truly will satisfy this curiosity, unfortunately.
Work with Windows professionally for a few years.
and yeah, everything is an object, and I see how that can be a nice idea, but man, does that force you to select properties of those objects like crazy. Is this really a good thing, once you have it figured out
This is like the only thing I actually like about PowerShell.
I am an IT technician, mainly focused on Windows, but I have also several years as a Linux sysadmin on my CV.
Now, you need to remember that Linux and Wondows have vastly different stratergies for how they work.
Linux, as you say, will allow you to view and service every part of it, as long as you know how, Windows on the other hand is more like a black box, you need to use special tools to get through the cover and access the information you may need.
Powershell is your friend, I have only written batchfiles, bash scripts and Powershell scripts for managing systems, and out of these I find Poweshell the easiest.
365… Microsoft loves to hide settings in the web UI, there are plenty of settings you can only set through Powershell.
VSCode is the best editor for Powershell as far as I am concerned, I highly recommend that you use it.
I get you on everything being either disconnected or surface level, unfortunately it just comes with experience mostly (same way as on linux). There are some deeper courses and books into specific windows services like exchange and AD that willgive you deeper understanding of everything.
I’m kinda on the opposite side of the fence. Windows/Dos stuff is pretty easy for me to grasp and understand but I’ve been working away at Linux for decades.
I found this training supplement to be quite helpful.
https://www.cbtnuggets.com/it-training/microsoft-windows-server
Also a useful resource.
https://learn.microsoft.com/en-us/dotnet/desktop/wpf/overview/?view=netdesktop-9.0
This is what Heath Ledger did to get into his role as the Joker. Proceed with extreme caution
Hahaha I lol’ed… and I’m afraid 😳


