The hospitality industry is currently navigating a profound digital transformation, where the integration of advanced systems into daily operations is no longer optional but imperative for survival. This study investigates the concept of Task–Technology Fit (TTF) within the specific context of hotel front office operations. The primary objective is to determine whether current technological tools—ranging from Property Management Systems (PMS) to mobile check-in applications—effectively support the multifaceted responsibilities of front office staff or if they introduce new operational friction. Adopting a qualitative research design, this paper analyzes primary data collected from 10 front office employees via open-ended questionnaires. The findings reveal a complex dichotomy: while digital tools significantly enhance speed and accuracy when functioning optimally, their benefits are frequently mitigated by system instability, poor integration, and inadequate training. The study concludes that for technology to truly fit the task, hotels must move beyond mere adoption and invest in holistic support systems, including continuous training and infrastructure upgrades.