This paper will discuss the Welsh Monastic Skyscape Study, initiated by the Sophia Centre at the University of Wales, Trinity Saint David. Seventeen sites were surveyed during this pilot project which covered over 1200 miles of travel, from northern Anglesey, to mountainous Snowdonia, down to the Beacon Beacons and then on to the southern lowlands. Cathedrals, abbeys, priories, churches and monasteries were measured for their orientation and possible archaeoastronomic intent. The survey team was made up of Dr Bernadette Brady, Dr Fabio Silva, Dr Darrelyn Gunzburg and Pamela Armstrong MA and this paper explores the fieldwork issues they faced at sites as disparate as majestic St David’s Cathedral, remote Llanthony Priory and ruinous Cymhir Abbey amongst many others. The buildings were in various states of decay which presented challenging on site demands as compass, clinometer, survey poles and tape were deployed in order to establish the relationship that the earliest Cistercians, Augustinians, Benedictines and Carmelites made with their skyscape. Medieval religious architects laid down the foundations of their belief systems, not just in the communities they established, but also in the architecture they designed. They will have had liturgies that were both written and spoken, but there may have been a third form of liturgy, one that found itself embedded in the relationship these architects forged with their local horizon. Our fieldwork was designed to measure that relationship to the sky, site by site, location by location and this paper looks at the fieldwork problems which emerged and the solutions put in place to complete this study.