At its height in the early 16th century the priory consisted of twelve brother priests led by a prior, who was often a secular nobleman who served as advocate in worldly matters.

Upon their majority they either left the monastery to marry or go to war, join the lay brothers in the hospital, or apply to become knight-monks and enter the priesthood.

Dueholm Priory had a long struggle with the town over Holy Ghost Hospital, which was established by the citizens of the town for the care of the poor and sick, and manned by lay brothers of the Order of the Holy Ghost who lived a religious life of service at the hospital.

The argument with the Hospitallers came when in 1445 Christopher of Bavaria, King of Denmark, recognized the town's rights to the hospital property which they had built.

Bishop Gert stood solidly in Dueholm's corner forbidding laymen or helpers from receiving benefit of donations to the hospital.

The dispute grew so hot that Christian I stepped in to order that the parish priest at St Clemens was not to be prohibited from saying mass in the hospital chapel, thereby giving St Hans Priory, who chose the priest for the parish church, spiritual control over the hospital.

The two books fell into the possession of 'the honorable and well-born lady Elle Krastrup, the widow of Thygge Sandberg of Kvelstrup and were preserved by her and then after 1587 passed on to the local magistrate.

The two surviving Dueholm letters provide glimpses into the everyday life of medieval monks and the surrounding community.

Since the main work of the brothers was to run the town hospitals, citizens had an interest in the continuance of medical services.