This work presents an imaging testing system (software and hardware) that can generate repeatable images through a stabilized port in the soil for processes known to change with time. The system includes (i) a stabilized port in the ground made of standard PVC pipe, with sections lined with a borosilicate glass tube, and (ii) a digital imaging instrument to survey the optically transparent portion of the stabilized port. The instrument uses a probe containing a digital camera and two light sources, one using white lights and one using ultraviolet (UV) lights (365 nm). The main instrument controls the probe using a cable within the stabilized port to take overlapping pictures of the soil under the different light sources. Two examples are provided, one to document the distribution of soil and groundwater contaminants known as non-aqueous phase liquids (NAPL, which include petroleum) at variable water saturation levels and a second one to monitor the growth of a plant over a 2-week interval. In both examples, the system successfully identified critical changes in soil processes and showed a resolution of approximately 15 µm (in the order of the thickness of a human hair), demonstrating the potential for repeated imaging of soil processes known to experience temporal changes. Both examples are illustrative, as additional applications might be possible. The novelty of this system lies in its ability to generate repeated measurements at larger depths than the current shallow systems installed by hand.