Social workers are at the forefront of hospital discharge planning, facilitating timely access to medical care through improved patient flow and promoting continuity of care through service coordination. Older adults, as consumers of the hospital system, are often referred to social workers to assist with a smooth transition back to the community. However, concerns about access to support, home environment, and other social factors may pose barriers to hospital-to-community transition. This study explored the experiences of hospital social workers discharge planning for older patients in Queensland at the time the Home Care Package was in operation. Qualitative semi-structured interviews were conducted with seventeen social work practitioners from metropolitan, regional, and rural Queensland hospitals. Challenges to discharge planning were identified during data analysis, particularly regarding return-to-home arrangements and social situations. The findings identified that inadequate and delayed access to Home Care Package-funded services, complex social situations, and geographical location could affect decisions about returning to or changing from the usual living arrangements. Participants supported patients and their families through difficult decisions to balance patient safety and autonomy. These compelled participants to adopt innovative practices, upending norms to manage organisational expectations, ethical dilemmas and moral distress. This study highlights the intricacies involved in discharge planning and substantiates individual drivers to discharge destinations post-hospital admission. Despite its focus on the previous aged care system, this research illustrates the relevance of its findings to the new aged care system and could assist practitioners with the transition from the Home Care Package to the new Support at Home program.