Despite a high score in Test of English as a Foreign Language (TOEFL) and a fluent command of English in non-academic contexts, international graduate students may find themselves struggling to write academic papers, perhaps almost immediately after they begin graduate education. Although graduate faculty can see variations on student papers, they may not realize what creates the variations, how they are created, and how significant they can be in task interpretation. This explorative study examined how three multilingual doctoral students developed an understanding of and negotiated pre-dissertation writing tasks. Interviews, papers with instructor comments, and field notes were collected from two sections of a course at a TESOL graduate program. The findings suggest that even experienced L2 writers engage in guessing and negotiation in order to understand and complete the writing tasks they are assigned. They indicate that from the beginning of defining a writing task, L2 writers engage in a guessing game and that a combination of guessing and self-positioning as a novice is a dominant feature of graduate academic writing. Although students encounter a number of complications while socializing into task expectations, successful socialization comes through the relative positioning of self and the academic community and implicit instruction.