The Australian bail system routinely permits most individuals accused of a crime to remain in the community while awaiting a court date under a range of conditions. However, statistics have indicated that a high number of bailees breach the orders placed on them, increasing police and court interactions, and resulting in additional charges. This project utilised the Drug Use Monitoring in Australia – Western Australia (DUMA-WA) collection to survey 230 police detainees about their orders and reasons for breaching recent orders. The results indicated that most understood their orders but disclosed a range of complexities which interfered with compliance. Qualitative responses revealed the themes of life complexities including homelessness and family responsibilities, and procedural challenges which served as barriers to adhering to order requirements. No significant differences were found based on Indigeneity; however, allowances for cultural obligations are essential to reduce breached conditions. General Strain Theory is used to examine the structural elements that arguably contribute to charge pile-ups and criminalisation for those on orders. While this paper utilised WA participants, given the similarities of detained persons in Australia, the issues identified provide suggestions to address the high levels of breaching conditions in other jurisdictions. There urgently needs to be a concerted effort to remove some of the procedural roadblocks to compliance which would reduce additional charges, reduce the workload of police and court staff, and assist with delays in the administration of justice.