When one is exactly at the critical angle, the light behaves in a way that may be interpreted as "something in between" refraction and reflection: it continues in a direction that is tangent to the boundary of the mediums.
When the angle is smaller than the critical angle, we get refraction. At the critical angle, $\theta_2$ of the refraction becomes 90 degrees, so we get the tangent propagation. At angles larger than the critical ones, there is a discontinuity: the equation for $\theta_2$ (arcsine of something) has no solutions which is why we get a total internal reflection.
There is nothing about these facts that would contradict reversibility or time-reversal symmetry of the laws of physics. If we time reverse the behavior at the critical angle, it indeed looks like the light must "randomly pick" a moment at which it enters the medium with the higher refraction index and there isn't any unique way to pick the preferred moment.
But that's not a problem because the probability that the direction of light is "exactly" tangent to the boundary is zero. In a real-world situation, the light will be a superposition of beams with angles $\theta_2=\pi/2-\epsilon$ for various small values of $\epsilon$, and for any nonzero $\epsilon$, the light will know very well when it hits the boundary. So your problem only occurs at a negligible, "measure zero" portion of the situation, so it is at most a "measure zero" problem. When one adds the appropriate degree of realism and specifies the precise angles and deviations from the "idealized model", the problem goes away.