The prize (so far) goes to one of my colleagues, who used to work for a software company that once sold a financial package to a customer on the basis that it had a particular module. The only problem was that it did not exist. He was asked to set up a "demo" of the software to the customer which sounds like something out of "The Office". In one room sat the customer at a screen, who typed in various data to the system and requested a report from an (entirely fictiitious) pick list of reports that the vendor was supposed to have built but had not. In the next room was a programmer. When the customer pressed "enter" the data would appear in a table, and they quickly manually edited a report format using the customer data, which was "off to the printer". A couple of minutes later the report was brought in to the customer, who could they see the new reporting module in action. The slow response time was explained by an "old server". Lest you think this was some fly by night operation, this major provider of financial software had over USD 100 million revenue back in the early 1990s, which was when this particular scam was perpetrated. And yes, they closed the deal.
As if to prove that enterprise software companies are still amateurs when its comes to dubious behavior, Sony has just made all the wrong headlines by placing what is essentially a clever virus on its CDs, purportedly to avoid digital copyright violations. The software installs itself into the root directory of your PC and, quite apart from preventing unathorised copying of music, also broadcasts back to Sony what music you have been listening to. Apparently million of PCs may have been infected, and only after several refusals have Sony now agreed to stop producing the spyware. Just what corporate manager at Sony thought this was a really bright idea that no-one would figure out is yet to emerge. However it is safe to say that Sony's PR agency are not having a quiet run-up to Christmas right now.
I'd be interested to hear about any reader's experiences of outrageous software company behavior.