This study examined how the Medical Orders for Life-sustaining Treatment (MOLST) is implemented in two nursing homes in Massachusetts; one had primarily long-term care residents and high hospice utilization, the other had low hospice utilization and a high proportion of post-acute care residents. Qualitative in-person interviews with 21 staff members who had a role implementing the MOLST explored their experiences using the form in their daily work routines. Staff at both nursing homes described benefits of the MOLST such as providing guidance for staff and family. Yet, they also gave detailed accounts of challenges they face in implementing the form. They reported problems with the form itself such as confusing language and conflicting categories as well as a set of procedural challenges that undermined the timely completion of the form. The nursing home with more post-acute care residents faced more challenges with transferability of the MOLST to and from hospitals.