Yes and no. This was the IT of a school, most likely low-paid College/University graduates trying to patch together a working system on a shoe-string budget 20 years ago. Maybe they were fully aware of the issues and struggled to get time to deal with them - try convincing an uneducated management that you need to fix something that is currently working.

I remember IT were continuously fixing computers/laptops broken by students, fixing connectivity issues (maybe somebody has pushed crayons into the Ethernet ports), loading up software that teachers suddenly need tomorrow, etc. Maybe they also have to prevent external actors from accessing important information. All the whilst somebody well above your pay grade is entering into software contracts without knowing anything about software.

Things are likely far more plug & play now for IT infrastructure, back then (XP I think) it was more the Wild West. Only five years ago I know that a University login system used to send username and password credentials via plaintext, because that's how the old protocols worked. The same University also gave me sudo to install/run programs, which provided sudo over all network drives.

You would probably be horrified to know how much infrastructure still runs on outdated stuff. Just five years ago the Chinese trains stopped working because Adobe disabled Flash [1]. I know of some important infrastructure that still uses floppy disks. Not so long ago some electrical testing could not be conducted because the machine that performed it got a corrupted floppy disk.

[1] https://arstechnica.com/tech-policy/2021/01/deactivation-of-...