During the last decades, educational contexts have transformed into complex technological and social ecologies, with mobile devices expanding the scope of education beyond the traditional classroom, creating so-called Ubiquitous Learning Environments (ULEs). However, these new technological opportunities entail an additional burden for teachers, who need to manage and coordinate the resources involved in such complex educational scenarios in a process known as “orchestration”. This paper presents the evaluation of the orchestration support provided by GLUEPS-AR, a system aimed to help teachers in the coordination of across-spaces learning situations carried out in ULEs. The evaluation, following an interpretive research perspective, relied on a study where a pre-service teacher designed and enacted an authentic across-spaces learning situation in a primary school. The situation, which illustrates the orchestration challenges of ULEs, was aimed at fostering orienteering skills. It spanned five sessions taking place in the classroom, in the school’s playground and at a nearby park, using multiple technologies and devices. The evaluation showed that GLUEPS-AR helped the teacher in the multiple aspects of orchestration, including implementation of his pedagogical ideas, adaptation in runtime, and sharing of orchestration load with students. Teacher awareness during outdoor activities was the main aspect to improve upon.