A large body of research exists which examines the advising of international students, but little work has been done to understand the ongoing difficulties that an individual student may face over time, during his or her stay in Japan. In order to better understand the way the situation of an international student may change over time, the author examined records of international students who had visited his advisory office 30 times or more, over a period of one year or longer. In total, 37 students met these conditions, with records dating from 1999 to 2014. These students may be informally divided into three types: 1) students who experienced a series of serious problems for the duration of their contact with the advisory office; 2) students who experienced a single serious problem, and who thereafter became leaders of their Student Union and supported the activities of the advisory office in that capacity; 3) students who visited the advising office without a serious problem. The greatest number of visits from a single student was 163, and the longest-running record for a single student lasted 12 years. The most representative cases had the following features: the students involved were candidates for doctoral qualifications who had problems with their supervisors; the students had arrived from China, Africa, or the Middle East; they had received a scholarship from the Japanese Government, and were undertaking a major in the natural sciences.