Poor social connection or loneliness is a prominent feature of schizotypy and may exacerbate psychosis risk. Previous studies have examined the inter-relationships between loneliness and psychosis risk, but critically, they have largely been conducted in non-clinical samples or exclusively used laboratory questionnaires with limited consideration of the heterogeneity within schizotypy (i.e., positive, negative, disorganized factors). The present study examined links between loneliness and psychotic-like symptoms across the dimensions of schizotypy through cross-sectional, laboratory-based questionnaires (Study 1; N = 160), ambulatory assessment (Study 2; N = 118) in undergraduates, and ambulatory assessment in inpatients in a substance abuse treatment program (Study 3; N = 48). Trait positive schizotypy consistently predicted cross-sectional and state psychotic-like symptoms. Loneliness, assessed via cross-sectional and ambulatory means, was largely linked with psychotic-like symptoms. Importantly, psychotic-like symptoms were dynamic: psychotic-like symptoms largely increased with loneliness in individuals with elevated positive and disorganized schizotypal traits, though there were some inconsistency related to disorganized schizotypy and state psychotic-like symptoms. Negative schizotypy and loneliness did not significantly interact to predict psychotic-like symptoms, suggesting specificity to positive schizotypy. Ambulatory approaches provide the opportunity for ecologically valid identification of risk states across psychopathology, thus informing early intervention.