2017 marked a century since the development and administration of the first large-scale group administered standardized test. Since that time, both the importance of testing and the technology of testing have advanced significantly. This paper traces the technological advances that have led to the large-scale administration of educational tests in a digital format. Through this historical review, a drive to develop and apply new technologies to increase efficiency is revealed. In addition, this review reveals a pattern in which each new advance unveils a new drag on efficiency that becomes the focus of future innovation. The interplay between a drive for efficiency and interest in improved validity is also explored. Upon reaching the recent introduction of technology-enhanced items, the paper suggests that it may be advantageous to relax the drive for efficiency with hopes of realizing gains in validity.