Becoming an experienced heritage specialist depends on your interests and on the opportunities that arise. Sometimes it also depends on the stubbornness you tackle the challenges that arise, and the gumption you set out on new paths. The boundary is a thin one: to propose oneself for new activities, to look for solutions to new problems, but also to guarantee the quality of produced results, adherence to set time constraints, and sustainability of undertaken projects. Technological advancements increase automation and speed of heritage documentation, but there are always complex scenarios in which experience and human-input play a fundamental role. Therefore, it is necessary to recall problems faced in similar situations, to invent new ways of proceeding, and, why not, to know whom to ask for help.

In these times, we have become accustomed to remote simulations of historical sites, heritage architecture, museums, and other places of cultural interest. However, we are just starting to learn how to benefit from them and how to use them for didactical purposes—especially for teaching new generations of documentation professionals. The proposed Tutorial will function as a teaching workshop collecting “behind the scenes” experiences and lessons learned from campaigns of large, monumental complexes, and other instances of significantly difficult heritage recording. The moderators would like to invite professional and academic teams which have taken part in such endeavors to showcase the strategies and solutions adopted to overcome certain challenges and to illustrate their way of thinking in doing so, but also how the decision making affected obtained results, from a didactical perspective. We believe that it may be of interest to the Emerging Professionals, and in general to the younger CIPA audience also to know the problems, the difficulties, the more practical aspects of work in the field – and in the office.