Acquisition or upgrading of technology has become as routine as purchase of consumables ever since the computer became indispensable to commerce. If the choice of hardware to buy is challenging, it is even more so for software. Although no data are available as evidence, it is safe to say that hundreds of billions of dollars have been wasted on unnecessary, inadequate or incompatible software by governments and economic entities all over the world. As there is yet no empirical research on this subject, this paper is an attempt to document common pitfalls in the acquisition of technology, especially software. The paper covers potential mistakes along the fairly common process starting from Request For Proposal (RFP) to Terms of Reference (TOR), then Proof of Concept (POC) and eventually System Integration Test (SIT) plus User Acceptance Test (UAT). It is the aim of this paper to provide some guidance for businesses trying to avoid errors that are often costly.