Connecticut's DSS Uniform Policy Manual, section 3029.05, sets the transfer look-back date at 60 months before the first date on which two things are both true: the person is institutionalized, and the person is applying for or already receiving Medicaid. The policy's definition of "institutionalized" is broad, covering long-term-care-facility services, equivalent medical-institution care, and Medicaid HCBS-waiver services alike. In everyday conversation this gets shortened to the "five-year look-back," but the exact triggering dates in the policy are what actually matter.
What the rule targets is any asset given away or sold for less than fair market value by the applicant or their spouse. DSS frames the consequence as a penalty period — a stretch of ineligibility for certain Medicaid services — rather than a tax on the gift itself. Whether a specific payment, deed, family transfer, trust contribution, or below-value sale counts as uncompensated depends on the state's policy exceptions and the evidence of fair market value on hand; it isn't something a family can safely decide just from how they've labeled the transaction.