Reciprocal parent-child interactions are theorized to play a crucial role in child anxiety development and maintenance. The current study tested whether toddler-solicited maternal comforting behavior in low-threat (mildly challenging and novel) situations may be a unique, early indicator of anxiety-relevant interactions. Controlling for other types of maternal comforting behavior, a path model tested solicited comforting behavior in a low-threat context in relation to both family accommodation (FA) and child anxiety symptoms, which may subsequently continue to predict each other over time. Identifying the emergence of this cycle in early childhood could bolster anxiety development theory and preventative interventions. Mother-child dyads (n = 166) of predominantly non-Hispanic/Latinx European American and socioeconomically diverse backgrounds were assessed at child ages 2, 4, and school-age via laboratory observation and maternal report. A longitudinal path model showed that solicited comforting observed in a low-threat situation at age 2 predicted mother-reported FA and child anxiety symptoms at age 4, above and beyond unsolicited comforting behavior and comforting behavior in a high-threat context. Furthermore, FA and child anxiety were bidirectionally related between age 4 and school-age assessments. Results suggest that toddler-solicited comforting in low-threat situations may be a unique indicator of child-directed anxiogenic family processes. The current study also expands the FA literature by providing empirical evidence for a bi-directional relation between anxiety and accommodation in young children.