NSF
If anyone invented the internet, it was the National Science Foundation. But the organization has ended up with a web-based system for submitting proposals (called Fastlane) that is so bad it is mindboggling. I tried over and over again to update the information they had in their system on me, and it kept telling me that email addresses with blank spaces weren't allowed. Finally our grant specialist cracked the problem, she hit delete several times before typing in my email address. Apparently the form was prefilled with several of the forbidden blank spaces. I don't know if the problem is that NSF developed its system too early and now is stuck with a system with older and less forgiving technology or the issue is that described by the astronaut who said that it wasn't encouraging to realize he was sitting on top of a rocket built by the lowest bidder. (The quote is variously attributed to Michael Collins and Alan Shepard.)