On a global basis, the usage of information technology in childhood pedagogy has been controversial. However, the trend of utilizing computers in preschool education is likely to gain momentum regardless of this controversy. This is particularly so for Singapore, a tiny country ranked only second to the United States in IT penetration and usage in the latest ranking by the World Economic Forum. In this regard, the attitudes of the various stakeholders (principals/administrators, teachers, and parents/guardians) are of utmost concern to both researchers and practitioners as such attitudes may shape the styles and methods of IT usage. Based on symbolic interactionism as the informing theoretical perspective, this study examines their perceptions toward IT usage in childhood pedagogy at seven preschool educational centers in Singapore. As part of our findings, we identify the existence of an “invisible” chasm and highlight factors that may be critical in crossing this chasm. In particular, we suggest possible extensions to Surry’s RIPPLES model, originally based on higher education, with accompanying implications for future research. We conclude with a proposed PIECES framework to guide effective IT usage in early childhood pedagogy.