This qualitative study investigated seven teachers participating in a professional development (PD) series on translanguaging pedagogies. The purpose was to better understand how teachers adapted translanguaging strategies into their classroom practice and how they perceived challenges and benefits of these approaches. Analysis of PD videos, interviews, and artifacts revealed teachers enacted a range of strategies from spontaneous to meticulously planned translingual scaffolding. The researchers explore two strategies in detail--multilingual word walls and literature discussion groups--with implications for teacher learning of translanguaging pedagogies. Reported benefits included student engagement and collaboration, and expansion of teachers' knowledge about students. Reported challenges included integrating translanguaging strategies into established routines, responding to a range of languages and language proficiencies, and negotiating administrative pressure to focus on other priorities. The study builds on these findings to develop notions of entry points and trajectories. Entry point strategies not only create opportunities for students to use their full linguistic repertoires during instruction, but help teachers think more deeply about students' multilingualism and the relationships between academic English and students' specific home and community languages. Trajectories describe how translanguaging practice develops from early attempts at enacting specific strategies to robust commitments to translanguaging praxis.