Little is known about how rural men experience and enact informal caregiving, despite growing caregiving demands and substantial male participation. This qualitative study used constructivist grounded theory to explore caregiving among 12 rural male caregivers in frontier areas of Montana and Oregon. Analysis revealed that caregiving stress was shaped by rurality and rural masculinity, with limited resources pushing caregivers toward crisis. Men negotiated conflicts between caregiving demands and constructed gender through preservation, compromise, or reconstruction, the latter fostering resiliency and appreciation of caregiving’s emotional value. A theoretical model is proposed, highlighting the need for gender- and culture-sensitive caregiver support services.