Simple intuition
Classically, not enough energy means no crossing. Quantum mechanically, the wavefunction does not stop sharply at the barrier, so there can still be a small probability of transmission.
Precise explanation
Solving the Schrödinger equation for a barrier gives a wavefunction that decays inside the barrier but is not exactly zero there. Matching the wavefunction across regions leads to a nonzero transmission probability.
Example or analogy
Analogy: imagine sound leaking through a wall even though it is strongly blocked. The analogy captures strong suppression, not absolute zero, but the real calculation comes from the wavefunction and boundary conditions.
Common misconception
Tunneling is not a particle borrowing energy and paying it back later. That is a popular phrase, not the actual explanation.