Even though a first-year writing course remains a near-standard component of the college experience, its "content" and the "path" students take to enroll in it are not so standard. Two recent changes at a public, land-grant institution with a selective admission policy and an undergraduate population of approximately 10,000 spotlight these variables (Indiana University 2015, University of Wyoming 2015a). First, the university revised and refocused its general education program (the new program launched in fall 2015). One change involved shifting away from a university-wide vertical "writing" requirement to a "communication" requirement, which reflects a national trend toward rethinking the role and definition of writing curricula, including the first-year composition course (see, for example, University of Kentucky 2015). "Communication" courses at the university will now feature consolidated instruction in writing, oral communication, and digital communication. Second, in 2013, the university's program for students admitted conditionally and deemed at risk launched a directed self-placement (DSP) process. The DSP enables incoming students to self-determine an appropriate, desired level of academic support for the cohort- based cluster of general education courses they take during their first year, including (but not limited to) the first-year composition course. This article considers the value of linking more explicitly incoming students' experience as digital communicators with their increasingly digital postsecondary communication futures. Doing so can help new students--and, perhaps, at-risk students, in particular--visualize success at a key transitional moment: the directed self-placement test. First, the impact of digital technologies on definitions of college-level writing and literacy practices is explored. Next, directed self-placement and its role as a literacy "barometer" for students are described. Finally, an argument is made as to how--and why--to reimagine directed self-placement in a way that more explicitly accommodates digital literacy as a larger effort to help at-risk students visualize success at a key transitional moment.