This study continues a long running effort to examine collaborative writing and editing tools and the factors that impact Task-Technology Fit and Technology Acceptance. Previous studies found that MS Word/email performed better than technologies such as Twiki, Google Docs, and Office Live. The current study seeks to examine specifically the impact of experience on these outcomes. Fortuitously, during the course of the study, Office Live was redesigned and renamed as Office 365, thus also allowing the examination of tool characteristics. In contrast to previous studies, Google Docs and Office 365 now performed significantly better than MS Word/email on the outcome measures despite users having significantly more experience with the latter. We speculate that as users gain experience with tools that perform the collaborative writing and editing task differently than did past tools, they perceive that the old technology no longer fits the task as well and thus it performs lower on outcome measures. We also observed that even though the Word/email technology did not change during the time of the study, its scores went down, possibly due to users' experience with newer technologies more suited to the task.