Background: Swallowing difficulties are common and complex in children with physical, behavioural, and cognitive needs. This study (i) describes mealtime management and (ii) identifies barriers and facilitators to implementation of a guideline for school-aged children with feeding difficulties in one specialist school. Method: Three data sets were collected: (i) 51 school records, (ii) 48 meal observations, and (iii) seven staff interviews. The model of behaviour COM-B (Capacity Opportunity Motivation and Behaviour) was used to identify barriers and facilitators. Results: 28 school records stated diet modifications and five children were enterally tube fed. Seventy percent of children had mealtime assistance. Only 25% of children had written plans and these did not contain all strategies observed. When feeding plans were vague or disagreements occurred, policy did not support decision-making. Conclusions: A coordinated approach is needed. Target areas for change include staff and family education; defined processes for cross-agency documentation and more detailed plans for all children.