Shock-wave boundary layer interaction is a commonly found flow phenomenon in transonic and supersonic aerodynamics. However, interactions involving laminar boundary layers have received relatively less interest, due to the complexity of transition. As a result, experiments were performed to study laminar boundary layers and their interaction with shock-waves. The Mach number was 1.65 and the unit Reynolds number was varied between 5.6 and 11 million \(\text {m}^{-1}\) . Pitot probes and hot-wire anemometry were employed for flow measurements. Experiments of the transition process of a natural laminar boundary layer captured the modal growth mechanisms of the primary instability, and a new time scale was found in the latter stages of the transition process. A new multi-sensor hot-wire probe was developed to study this new time scale, which revealed strange physical properties. Experiments of transitional SBLIs were performed on a \(6^{\circ }\) and a \(10^{\circ }\) compression ramp. A new non-dimensional parameter was developed for scaling the strength of the imposed shock, that was able to reconcile the large scatter in a diverse collection of length scales of transitional interactions. Measurements of the boundary layer transitional mechanisms over the interaction showed an accelerated growth over the separated shear layer, but surprisingly the growth of sub-harmonic instabilities was bypassed at reattachment. Finally, low-frequency unsteadiness at separation was found at Strouhal number of 0.05, similar to other studies on transitional interactions. A possible link between the presence of non-linearities over the separated shear layer and the low-frequency unsteadiness was found.