March 2020 changed the world of learning. Ever since, students have been relying on remote lecturers, virtual fellow students, and electronic learning material. For many, this greatly differs from how they used to learn before and even though technology is incremental to students' everyday life, many are not familiar with using technology for their learning. The purpose of this study was to investigate if first-year college students are prepared for learning with technology and to empirically document possible gaps. To assess this, two successive first year cohorts completed a 32-items questionnaire that was based on standardized scales to assess time management, collaboration, and self-directedness, as the three core competencies for higher education learners to successfully engage in learning with technology. The answers were related to students' prior experiences and their motivation to learn online. First results indicated that time management is a major challenge for first-year students with and without work experience. Results also suggest that the motivation to learn has a positive relationship with the concept variables chosen to assess first-year students' expectation and readiness for online learning. The findings may support the need for higher education institutions to understand students' expectations and self-assessed readiness and to identify areas for improvement.