As collaboration among teams that are distributed in time and space is becoming increasingly important, there is a need to understand the efficacy of tools available to support that collaboration. This study employs a combination of the Technology Acceptance Model (TAM) and the Task-Technology Fit (TTF) model to compare four different technologies used to support the task of collaboratively creating and editing a report. The characteristics of the four technologies operationalize different collaborative processes and quality of the editor enabling the examination of how well each addresses previously identified challenges to electronic collaboration. The study compared the use of MS Word combined with emailing the document among collaborators, Twiki, Google Docs, and Office Live by university students to collaboratively write a research paper. The study measured Task-Technology Fit, Perceived Ease of Use, and Perceived Usefulness of the technologies. The findings suggest that certain technological factors associated with the collaborative tool can impact effective use of the tool. A powerful interface with which the user has some experience is necessary, and support for distributed collaboration can be the distinguishing factor in making a tool an effective collaborative writing and editing technology. Our study suggests that Word/email and Google Docs outperform Twiki and Office Live due to tool experience and superior Task-Technology Fit that may be due to the sophistication of the writing and editing tool, support for collaboration, and the clarity of the collaboration process.We speculate that the surprisingly poor showing for Office Live is due to mixing a familiar editing interface with a collaborative model that is different from students' mental model of collaboration, leading to a phenomenon similar to the 'Uncanny Valley,' which is the experience of many people when interacting with humanoid robots and animations that have very good, but not perfect, realism.