With red supergiants (RSGs) predicted to end their lives as Type IIP core collapse supernova (CCSN), their behaviour before explosion needs to be fully understood. Mass loss rates govern RSG evolution towards SN and have strong implications on the appearance of the resulting explosion. To study how the mass-loss rates change with the evolution of the star, we have measured the amount of circumstellar material around 19 RSGs in a coeval cluster. Our study has shown that mass loss rates ramp up throughout the lifetime of an RSG, with more evolved stars having mass loss rates a factor of 40 higher than early stage RSGs. Interestingly, we have also found evidence for an increase in circumstellar extinction throughout the RSG lifetime, meaning the most evolved stars are most severely affected. We find that, were the most evolved RSGs in NGC2100 to go SN, this extra extinction would cause the progenitors initial mass to be underestimated by up to 9M$_odot$.