Sometimes users need to be asked if they need help. This is difficult with online users, because in-person cues cannot be used to engage when the users need assistance. Proactive chat widgets help to solve this problem as the chat box slides out onto the screen and prompts the user for help. The need for the proactive chat widget was also seen as EZproxy data revealed only 1% of online students who accessed the library's resources reached out for help through chat. This article will cover the successes and challenges of implementing a proactive chat widget on the library's Web site, catalog and databases; the review of proactive chat software; the collaboration of departments within the library to test and launch the widget; chat transcript analysis for coverage and training; and roles of the different departments staffing the chat service.