Hi! Yes you should repot. When you have the plant out of the pot, cut off any roots that are brown, squishy or dried out. Heathy roots are green and white and firm. Make sure to repot in orchid bark, preferably fine bark. Don't use landscape bark. Make sure you cut off the roots with a sterile, sharp blade. Cut off the bottom of the central stem of the plant if it is rotted. The bark should come up to the bottom leaf when you repot. These guys like to be watered so that they never completely dry out, yet they cant tolerate being left in standing water.