Learning in the current 2013 curriculum is based on contextual issues based on questions that can encourage students to think broadly. HOTS is a real-life based assessment of everyday life, but in practice, the students are having trouble completing the HOTS issue. Learning difficulty is also influenced by personality type Based on the fact that the real difference one can see from a person is behavior. Kersey classifies the personality into 4 types, namely Idealist, Rational, Artisan, and Guardian. The researcher focuses on the type of guardian personality that is the type of personality that does not like the picture. This study aims to describe the difficulty of learning mathematics in students with a type of guardian personality in the completion of Geometry materials especially in solving HOTS. This research type is descriptive qualitative research. Instruments used in this study were the researchers themselves, personality class test sheets, learning difficulty test sheets in the form of HOTS Geometry test, and interview guides. The results showed that students with guardian personality it was found that a total of 3.37 % difficulties of number fact skill, 4.49 % difficulties of arithmetics skill, 37.08 % difficulties of information skill, 31.46% difficulties of language skill, 23.60 % difficulties of visual-spatial skill.