This study explored informal caregivers’ experiences of transitioning an older adult into long-term care (LTC). Qualitative description guided our analysis of semi-structured interviews with 13 informal caregivers of older adults from three LTC homes in southern Ontario. Our findings illustrate that caregivers experience chronic worry and burden before deciding on, or requiring to apply for, LTC. A sense of lack of control was a prominent theme, especially when caregivers were applying for LTC beds. Participants perceived pushing, pressure, and punishment from the health care system and felt relieved and fortunate after they accepted a bed offer. This tumultuous experience stimulated caregivers to anticipate future transitions. It is recommended that caregivers receive preparation and targeted support to manage transition experiences. Improved communication among health professionals is essential. Penalties for declining an offer for a bed in LTC should be re-examined in relation to its negative influence on caregivers’ experiences.