Animated GIFs are increasingly popular in text-based communication. Finding the perfect GIF can make conversations funny, interesting, and engaging, but GIFs also introduce potentials for miscommunication. Through 24 in-depth qualitative interviews, this empirical, exploratory study examines the nuances of communication practices with animated GIFs to better understand why and how GIFs can send unintentional messages. We find participants leverage contexts like source material and interpersonal relationship to find the perfect GIFs for different communication scenarios, while these contexts are also the primary reason for miscommunication and some technical usability issues. This paper concludes with a discussion of the important role that different types of context play in the use and interpretations of GIFs, and argues that nonverbal communication tools should account for complex contexts and common ground that communication media rely on.