Visual communication is an integral aspect of Design and Technology (D&T) education. Students can learn a variety of skills by being exposed to the fundamentals of visual design by means of practicing colour theory, symbolism, layout, etc. In our attempt to provide engaging and rich D&T resources for schools, we design and develop design problem-solving activities for teachers and students. Said resources are open-source design activities available on our institute’s website. An outreach workshop focusing on a visual design task conducted on an open day was the basis of one such resource. This paper describes the insights gained from the said workshop, where sixty-nine students from the primary and middle schools participated in groups and worked on a visual design task involving designing flags for fictitious countries. Social science classrooms (Schramm-Pate and Lussier, 2003) use flag-based activities to introduce students about topics from history, culture, etc. Research (Dolinko, 1996; Kim and Simms, 2002) also shows that flags are a rich source of teaching mathematical concepts such as symmetry, geometry, proportions and fractions. In our design workshop, the groups of students had to work within a set of constraints such as fixed size and shape of the flag, using a limited number of colours without using any text. The analysis criteria were based on the flag drawings as designed by the students along with the brief write-ups in their assigned worksheets. The flags were examined on the basis of symbolic representations, design elements, colour selection, and stances of a dominant element. The preliminary analysis suggests that although a few of the student groups were able to create some abstractions, and symbolically represent the design brief; their flag designs had prominent visual influences such as presence of stripes or a central element that appear to stem from their knowledge of existing flags.