Central to the Learning Sciences is an interest in promoting cross-setting learning, including early workplace settings. This study conceptualizes ‘brokering pre-professional learning opportunities’ as a practice that goes beyond facilitating access across settings to include concerns about when, exactly, an opportunity is ‘safe enough’ when supporting connections for minoritized youth populations. Utilizing a design-based research approach, we report results of an organizational ‘vetting’ routine used to assess whether companies being considered for work-placement sites were appropriate for minoritized youth of color. Our findings confirm that characteristics of staff diversity and equity orientation of work-placement organizations can support or hinder positive learning outcomes. However, we also found that both strengths and limitations in terms of diversity and equity, in concert with other supportive factors, can be productive resources within the context of future goal setting for youth of color. We close with implications for those interested in promoting equity-oriented cross-setting learning.