Despite the potential positive effects of usingtechnology with students who have difficulties in mathematics inthe Kingdom of Saudi Arabia and the great efforts made by theSaudi Government to improve the education system of thenation, which has included a continuous rise in the educationalbudget, there still remain some obstacles for some teachers whenusing technology, and while some of these teachers overcomethese barriers, others do not succeed in this the challenge. Thispaper will investigate the barriers that teachers face when usingtechnology in their classroom in primary schools, and why someovercame obstacles while others did not. Semi-structuredinterviews and observations were used for the purpose of thisresearch, which were undertaken with three mathematicsteachers from school A which used technology, and the otherthree from school B, which did not use technology. I found thatthe major obstacle teachers face when using technology includedaspects of the teachers’ negative attitudes and beliefs aboutteaching mathematics using technology, the lack of training inusing technology, and the lack of technical support. The headteacher’s attitude was also an important influence on managingthe challenges teachers faced, which affected teachers’ decisionsto use or not use technology in school