As a part of the ongoing H i survey by the consortium for Galactic studies with the Arecibo L-band Feed Array (GALFA-HI), we have recently imaged the tip of the MS and found several long filamentary structures. This demonstrates that the northern portion of the MS, which has been interacting with the Galactic halo for a long time, is more extended than previously thought and in the form of highly organized H i structures. The observed filaments, and especially the kinematic dichotomy of H i clouds observed for the first time, agree with predictions by the Connors, Kawata & Gibson (2006) tidal model. However, specific time-stamps in the history of the Magellanic System are required to explain these phenomena. The 20-degree long filaments are accompanied by a large population of small H i clouds. We investigate the observed properties of these clouds and explore various instabilities that affect a warm tail of gas trailing through the Galactic halo. Interestingly, if the observed H i structure is mainly due to thermal instability, then the tip of the MS is at a distance of ~70 kpc.