What it means in practice
The federal Medicaid lookback is 60 months for most asset transfers (California is 30 months, and was supposed to phase out the lookback entirely, but implementation is incomplete). When a person applies for Medicaid long-term care, the state reviews every asset transfer in the lookback window. Each disqualifying transfer (gift, sale for under fair value, transfer to a non-qualified trust) creates a penalty period of Medicaid ineligibility.
The math: the disqualifying transfer dollar amount is divided by the state's "penalty divisor" (the average monthly nursing-home cost — varies by state, typically $8,000-$13,000) to determine months of ineligibility. Gifting $100,000 to your children in a state with a $10,000 divisor creates a 10-month ineligibility period — Medicaid won't pay for nursing care for those 10 months, even though the patient is now medically and financially eligible.
The ineligibility period starts when the patient applies for Medicaid AND would otherwise be eligible. So the brutal math: a family gifts $100,000 in year 3 of a parent's decline. In year 5, the parent enters nursing care. The family applies for Medicaid. They're inside the 5-year lookback. The 10-month ineligibility period starts THEN — at the worst possible moment, with the parent in nursing care costing $10,000/month, family has to come up with the next $100,000 from somewhere.
What does NOT trigger the lookback: transfers to a spouse (no penalty), transfers to a disabled child (no penalty), transfers to a special-needs trust for a disabled child, certain caregiver-child transfers (when an adult child has lived with and provided care for the parent for 2+ years preventing institutionalization), payments for legitimate goods and services at fair market value.
Proper Medicaid planning works WITH the lookback, not against it. Strategies that have a chance of succeeding: irrevocable Medicaid trusts (must be set up 5+ years before need), Medicaid-compliant annuities (in some states, for the community spouse), proper spend-down on exempt categories, life-estate deeds (in some states). All require an experienced elder-law attorney.