Business Administrators And Software Licensing

Gorbie asks: "It seems that there is a never ending battle between me and my company over software licensing. Whether I agree with the current laws pertaining to licenses, I adhere to them. My company is often unwilling to spend the necessary capital for the proper amount of licenses, and I get put in the position to either do what I am asked or risk major friction with my boss and the ownership of the company. Are there some licenses that I should worry less about? Client access licenses? Fonts? What are my risks?" When placed between the licensing and your boss, how do you handle your software?