I worked a job where to get something scanned you had to go the neighborhood mailbox place and FAX it to the fax number this org had so it would show up electronically.
I kid you not - obviously they had a deal on faxing for like 50% off, but it was still SUPER timeconsuming and pretty expensive.
Anyways, I configured one of their state of the art copiers to allow them to securely scan to users local folders. I set permissions dropbox style (upload, list but no read / download / delete). It was like I was a god briefly. Then someone in IT found out and the party ended big time.
Realize this isn't that long ago - we are talking some orgs / IT departments are SERIOUSLY retro. I could tell many funny stories (and some sad ones) about folks working around the IT department.
Another common IT workaround was that if a device was not on approved list (basically everything except some junky low bid stuff and definitely no no macs / no ipads) and you had a need (ie marketing / media department wanted to do something with kids shooting and editing video as a feel good, and ipads were great for that and the offical machines sucked) is they would hire a consultant to help them edit, and then put a procurement for the equipment through the consulting bill. Consultant got to mark it all up, but it didn't have to go through the IT purchasing process where ipad's were banned. Was time consuming but I saw it work.
Anyways, I know EXACTLY the type of org who buys these expensive video conferencing systems that fall over when you need them!