A level-shifting output buffer has cascode transistors with varying rather than fixed gate bias voltages. An adaptive regulator bypasses the I/O pad voltage to a regulator output when the I/O begins switching, but later clamps the regulator output to a middle bias voltage. The regulator output can be applied to a supply terminal of a buffer that drives the gate of the cascode transistor. Since the adaptive regulator follows the I/O pad voltage as switching begins, a voltage boost is provided to the gates of the cascode transistors, allowing for higher currents or smaller cascode transistors and preventing over-voltage stress. The adaptive regulator has an n-channel bypass transistor between the I/O pad and the regulator output, and an n-channel clamp transistor between the regulator output and the middle bias, with a gate driven from the I/O pad by either a p-channel gate-biasing transistor or an n-channel gate-biasing transistor.