Laboratory trials were carried out in order to clarify the interaction between felt and web structure and its impact on dryness variability. Oriented laboratory sheets of 80gsm and consisting of 100% never dried unbleached softwood kraft were prepared using a dynamic sheet former. The sheets were pressed with two different orientations; aligned with the felt aligned in the machine direction or with web aligned in the cross direction. The wet web samples were immediately transferred after pressing to a hot plate and dried under restraint. A bench-scale method was developed using near infrared (NIR) imaging in order to characterise the interaction between felt and web structure during pressing and drying. It was found that the average press dryness had a low dependence on interactions between web and felt structure. Moisture variability in the interaction layer was found to be highly dependent on the web fibre orientation relative to the press felt. High levels of moisture variability on the web surface were observed with large differences in fibre alignment. It was observed that moisture variations in the web surface after pressing continued through the drying process and further increased the total drying time of the paper web.