A struggling liberal‑arts college in Western Massachusetts reported enrolling roughly half its recruitment target, amplifying concerns about financial sustainability at small private colleges. Hampshire College enrolled about 150 first‑years against a 300‑student target, leaving total full‑time enrollment under 800. The president cited intensified competition, shifting waitlist practices at peer schools, and demographic pressures. Sector analysts point to standard warning signs—declining yield, persistent operating deficits, and governance strain—and offer a checklist of death‑spiral indicators that include rising tuition dependence, program cuts, and accreditation stress. Trustees and state policymakers are examining contingency measures like teach‑outs, mergers, and mission realignment. Regional leaders should accelerate collaborative transfer pathways, shared services, and targeted recruitment to stabilize enrollment. Boards must run scenario planning and contingency budgets now to avoid abrupt closures that leave students stranded.