arXiv:2611.09260v1 Announce Type: cross Abstract: In the age of digital transformation, companies are increasingly relying on specialized software to manage the complexity of projects. However, when selecting tools, features and costs often take precedence over user experience (UX), leading to low adoption rates, user frustration, and project delays. This study empirically evaluates the user experience of leading project management tools (Jira, Trello, Monday.com, Asana, and Microsoft Project) across various project scales using a mixed methods approach. The System Usability Scale (SUS) was used as the primary quantitative instrument, with data collected from 141 experienced professionals via online questionnaires. The results reveal a significant trade-off between functionality and usability. Trello achieved the highest SUS score (77.5), indicating a superior user experience for small projects and agile teams, while Microsoft Project scored the lowest (51.2), suggesting significant usability challenges despite its robust features. Jira demonstrated a balanced profile, offering powerful features with manageable complexity. Statistical analyses confirmed that the choice of the optimal tool is highly context dependent, with team size and project complexity influencing UX outcomes. The findings underscore that UX is not a secondary feature but a critical success factor for software acceptance and project effectiveness. This study provides an evidence-based framework for aligning tool selection with the project context, offers practitioners actionable insights, and identifies design opportunities for software developers.