There are some valid reasons for asking for a discount, such as plans to buy a large quantity of licenses, pay for a year in advance, the company is a charity,

There are some valid reasons for asking for a discount, such as plans to buy a large quantity of licenses, pay for a year in advance, the company is a charity, non-profit, school, etc. If the request for a discount didn't have some sort of justification like this then I still wouldn't write them off, but I would probably make a mental note. Regardless of the size of their company, some customers will never be content unless they bend you over backwards so far that you're losing money on their business. They want to get more value than they paid for. Whether that's because they don't appreciate the value of resources they consume, or it's intentional, I can never tell. On the flip-side, the weird thing is that these difficult customers can also wind up being your hugest fan. It can be a real love/hate relationship!