Gifting can be joyful and generous—but it also comes with important tax and legal considerations.

In this episode of Into the Woods, attorney Hannah Cannon joins host Dave Shaffer to demystify the rules around gifting: when it’s reportable, how it affects your estate and Medicaid eligibility, and why timing can be everything. They explore the gift tax annual exclusion, how gifting fits into your broader estate plan, and how even Oprah’s legendary car giveaway would raise legal questions.

^{Disclaimer: Episode recorded before passage of the One Big Beautiful Bill Act and the extension of the current federal estate tax exemption to $15M in 2026.}