An important institutional and societal dilemma is how to notify people when they are not meeting performance standards, such as in placing people on a probationary status at school or work. A critical and underappreciated aspect of this dilemma, this dissertation suggests, is that people commonly understand themselves to be in relation with valued institutions that structure their lives. Notification that one is not meeting standards, especially when the notification comes from a valued institution itself, may place this relationship at risk. Insofar as the relationship is valued and experienced as a sense of belonging, notification may lead people to feel ashamed, be concerned that they are stigmatized, and ultimately withdraw from the context, even when that is not adaptive and not what institutional actors intend. Across nine studies, I examine these processes within the context of college students being placed on academic probation. College administrators overwhelmingly reported that they intend probation to both inform students of unsatisfactory performance and support them in remedying it. Students readily identified the first intention from typical probation notification letters but not the second. Consistent with the theory that placement on probation functions a threat to a valued relationship, students who had previously been placed on probation described the probation process as characterized by feelings of shame and stigma. They articulated experiencing worries about belonging and devaluation and identified the probation notification letter as a salient aspect of their experience. Is it inevitable that probation notification letters elicit high levels of shame and stigma? No. Across diverse student samples, "psychologically attuned" probation notification letters designed to explicitly address concerns about belonging and devaluation reduced students' feelings of shame, concerns about stigmatization, and intentions to withdraw from college relative to typical probation notification letters. Can psychologically attuned probation letters to also improve students' academic outcomes in addition to their psychological outcomes? A randomized field intervention with five cohorts of students being placed on probation yielded some, but inconsistent, evidence that they may. A design process to develop contextually specific psychologically attuned probation letters is discussed. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]