This thesis investigates the dynamics of electrons ionized by strong low frequency laser fields, from a semiclassical perspective, developing a trajectory-based formalism to describe the interactions of the outgoing electron with the remaining ion. Trajectory models for photoionization generally arise in the regime known as optical tunnelling, where the atom is subjected to a strong, slow field, which tilts the potential landscape around the ion, forming a potential energy barrier that electrons can then tunnel through. There are multiple approaches that enable the description of the ionized electron, but they are generally limited or models derived by analogy, and the status of the trajectories is unclear. This thesis analyses this trajectory language in the context of the Analytical R-Matrix theory of photoionization, deriving a trajectory model from the fundamentals, and showing that this requires both the time and the position of the trajectory to be complex. I analyse this complex component of the position and I show that it requires careful handling: of the potentials where it appears, and of the paths in the complex plane that the trajectory is taken through. In this connection, I show that the Coulomb potential of the ion induces branch cuts in the complex time plane that the integration path needs to avoid, and I show how to navigate these branch cuts. I then use this formalism to uncover a kinematic mechanism for the recently discovered (Near-)Zero Energy Structures of above-threshold ionization. In addition, I analyse the generation of high-order harmonics of the driving laser that are emitted when the photoelectron recollides with the ion, using a pair of counter-rotating circularly polarized pulses to drive the emission, both in the context of the conservation of spin angular momentum and as a probe of the long-wavelength breakdown of the dipole approximation.