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r/sysadmin · u/bishoptfAug 1, 2026, 3:03 PM

The dreaded documentation question....sigh

I have supported part time a small non-profit company and while I know how important documentation is there just always was something else pressing that was more important. Well I am getting to the point where in the future I am probably going to be moving on and have started to work on trying at least for me document what they have at a high level. I assume and I know what happens when you do that but they have enough technical stuff that if the person actually knows what they are doing then they should be able based on a overview of the systems function dig into it and figure things out. I am not doing anything esoteric but I also have been doing this kind of stuff for *cough* many years. While small they have a lot of technology, just migrated the virtual environment to proxmox, they have AD environment with ADFS connected to m365, etc...

I just captured the inventory for everything they have and was about to start writing up a word document that gives a high level for each server etc, layout of the network, vlans etc. I then started to think that maybe I should do something like a wiki or use something else. Although at a high level kind of leaning towards not having it online since it would pretty much give you a working layout of their environment and if compromised would be pretty nice to have.

Just thought I would ask what are folks using for documentation, thanks.

110

Comments

u/BrorBlixen1Aug 1, 2026, 3:17 PM
We use Hudu which may or may not be the best fit for you. It's really easy to get bogged down in analysis paralysis trying to find or customize the perfect tool. If I were in your position I would just start with what I have available which would most likely be OneNote. Once you have the important stuff recorded you will have a better idea if a wiki or other tool would be beneficial.
- u/bishoptf1Aug 1, 2026, 3:29 PM
  Yeah, I think I am just going to pound out a word document (actually libreoffice writer) and call it a day. I do think if I had stood up a wiki site or something like it way back when that maybe I would have been better at keeping something up to date. Being part time support doesn't lend itself to being able to spend much of any time with so much work to get done. The other thing that I have decided to do is to keep it at a high level, document what they have but not go into the details since that would just take to much time. Been around the block and \*cough\* older and I am not doing anything esoteric but when I start to look at the environment there is a lot going on. Virtual servers, AV servers, wireless controller stuff, AD, File shares, backup...oh and voip infra. I was going to just lay out at a high level each item and what its doing service wise etc, all of the passwords are stored in a password manager with hardware key MFA access for access but if whoever takes over has no idea about how vlans work and this other stuff its not going to go well. I am kind of a dinosaur at this point where I worked in lots of areas and was able to do just about whatever was needed. I guess maybe AI will help them figure it out, lol....
u/wowsomuchempty1Aug 1, 2026, 3:29 PM
Git, caddy server, mkdocs.
u/tehwallace1Aug 1, 2026, 3:30 PM
get it written down anywhere first. organizing and sorting it is the easy part.
u/plump-lamp1Aug 1, 2026, 3:35 PM
Microsoft shop? Just start with loop
- u/Random_Effecks1Aug 1, 2026, 6:46 PM
  Wild call
  - u/plump-lamp1Aug 1, 2026, 6:50 PM
u/Junior-Tourist34801Aug 1, 2026, 3:37 PM
Yep. They should hire a low level to document person. But I do like how AI can really help here. If it knows what you did, it can document til the cowa come home. Try it.
u/richie-wales1Aug 1, 2026, 4:28 PM
I use Mind Maps to make diagrams of where everything else, how it links together, where backups go etc etc, then number them and then number the boxes and then write up details notes if needed on each one. Mind Maps are quick to capture main points and links, and infinitely flexible, and easy for other people to follow. Or sometimes, if I need something with a more specific layout I'll use something like OmniGraffle to create flow charts and diagrams. Diagrams and something visual are usually worth more than words alone.
u/pdp101Aug 1, 2026, 4:51 PM
I don't care for the "word processor as a documentation platform" model, but frankly you should not overthink this. Just start writing and don't hold yourself back, until you find that you're repeating yourself.

We use plaintext files in Git. In practice, we're very forgiving about the format and content of documentation, even though we're technically standardized on ReStructuredText format and not markdown or .txt.

just migrated the virtual environment to proxmox,

Good job, getting that monkey off their back. You're a credit to the profession.
- u/bishoptf1Aug 1, 2026, 6:33 PM
  Yeah it was kind of funny since I have been doing this for so long, when I originally was looking at virtualization many years ago for them I looked at proxmox. I am a linux guy so very comfortable with anything Linux but VMware was very generous for non-profits and the base essentials license (non vmotion etc) was basically free, cost like $30/year. I decided to go with VMware since I felt like it was solid and everyone knew it so if I was no longer around anyone would have been able to come in and manage it for them. Fast forward to Broadcom just going scorched earth with pricing, was an easy decision to move them to proxmox, much more popular now and lots more folks supporting it so I feel like finding someone to manage it will be an easier task now. I also took the opportunity to move their existing veeam instance from the winblows server to the new linux software appliance, so lots of work has been done.
u/strikesbac1Aug 1, 2026, 5:13 PM
I’d get ITGlue or if no budget, use Obsidian along with Diagrams.net
u/FatBook-Air1Aug 1, 2026, 6:17 PM
We use a web platform called Outline. It's open source, but we just use the hosted version, which costs $100/year for 10 users. Well worth it IMO.
u/doglar_6661Aug 1, 2026, 6:46 PM
I would personally use Markdown to write up documentation. In your case, perhaps a Word doc for high level and a spreadsheet to list the core FWDNs, IPs and VLANS. You don't need to write out a low level design, just make it clear what exists. That plus the credentials should be enough for a clean handover.
- u/bishoptf1Aug 1, 2026, 6:57 PM
  Yeah kind of what I am hammering out, I have a high level network diagram, an inventory spreadsheet with all of the vlans and devices and a working on a word document that gives high level information about most of the service devices.