Structured reporting contributes to the completeness of radiology reports and improves quality. Both the content and the structure are essential for successful implementation of structured reporting. Contextual structured reporting is tailored to a specific scenario and can contain information retrieved from the context. Critical findings detected by imaging need urgent communication to the referring physician. According to guidelines, the occurrence of this communication should be documented in the radiology reports and should contain when, to whom and how was communicated. In free-text reporting, one or more of these required items might be omitted. We developed a contextual structured reporting template to ensure complete documentation of the communication of critical findings. The WHEN and HOW items were included automatically, and the insertion of the WHO-item was facilitated by the template. A pre- and post-implementation study demonstrated a substantial improvement in guideline adherence. The template usage improved in the long-term post-implementation study compared with the short-term results. The two most often occurring categories of critical findings are “infection / inflammation” and “oncology”, corresponding to the a large part of urgency level 2 (to be reported within 6 h) and level 3 (to be reported within 6 days), respectively. We conclude that contextual structured reporting is feasible for required elements in radiology reporting and for automated insertion of context-dependent data. Contextual structured reporting improves guideline adherence for communication of critical findings.