Any form of flexible learning necessitates an assessment of technological preparedness of the stakeholders. This study aimed to assess the technological preparedness of Pangasinan State University (PSU) as it implements flexible learning modality (FLM). Participated in by nearly 20,000 students through a survey conducted during the School Year 2020-2021, findings showed a general technological preparedness of the students for online learning. Main challenges found included intermittent power interruptions in various municipalities in the Pangasinan, Philippines during the early phase of FLM, as well as the poor internet connection. Issues found included costly purchase of mobile data, stress on multiple online submissions of requirements, preference of printed study guides, no learning spaces at home, and technical difficulties on the use of the online learning platform used by PSU. Recommendations include re-alignment of unused funds on printing services for the purchase of mobile data for qualified students, synchronous submissions of requirements online per college, and task-based orientation on the use of the platform. These findings were even micro-analyzed in one of its campuses, the Lingayen Campus to provide a campus-view on the implementation of the online modality. This book will help in answering the question - are we prepared for online learning?