Development of two-digit place value understanding in the elementary grades has been the subject of some study; however, research at the pre-kindergarten (Pre-K) level is limited. This two-part paper begins by providing an overview of two-digit place value instruction in Pre-K and describes the component parts of a research-based math curriculum, "MyTeachingPartner Math" ("MTP Math"). Part two presents the results of a video analysis of classroom interactions across four "MTP Math" place value activities facilitated by two high quality teachers. Particular attention is given to the primary conceptual hurdles faced by students, as well as the scaffolding strategies employed by teachers. Results indicate that students possess a conceptual understanding of the ones place prior to the tens place and initially struggle the concept of unitizing groups of ten. Considerations are discussed for improving the quality of teacher-child interactions in pre-kindergarten that can best support children's thinking and learning.