This article capitalizes on the notion of linguistic risk-taking by focusing on a new pedagogical initiative at the University of Ottawa, an institution where courses, programs, and services in both English and French are available. In this bilingual context, we define linguistic risks as authentic communicative acts in learners' second official language (French/English) which may be "risky" due to factors such as making mistakes, being misunderstood, misunderstanding others, being judged, taking on a different identity, and changing previously established language-choice patterns. This may cause learners to miss campus-wide opportunities for authentic and meaningful second language engagement. To encourage risk-taking, we designed an initiative offering a Linguistic Risk-Taking Passport (a 26-page booklet with over 70 risks) distributed to over 500 French/English learners. The risks represent authentic activities available outside the language classroom (e.g., speak the second language at the library, approach a passer-by for directions, order food at the cafeteria, interact with professors/administrators, attend events, etc.). Learners autonomously check off risks in their passports, comment on difficulty levels, propose additional risks, and can submit passports for prizes. We survey theoretical constructs related to linguistic risk-taking, detail the development of the initiative, and conclude with future directions, including technology use.