Proactive chat help has gained attention in academic libraries for increasing the number of questions from online users. Librarians have reported a significant increase in chat traffic, particularly related to research. So far, library websites have been the primary target of proactive chat implementation efforts, leaving subscription databases largely untouched and their users without help. This article describes how librarians at the University of New Mexico collaborated with vendors to embed proactive chat in databases, detailing the process, technical glitches, and use trends. With this project, librarians have pushed the boundary of chat help into territory rich with opportunity to directly support online scholars at their point of need. Insights outlined here would be useful to librarians considering expanding their chat reference service to subscription databases and those interested in connecting help services to online users.