But, overall, we can say that tattoos covering scar tissues do hurt. Some would say they hurt even more than the regular tattoos done on unscarred skin. Moreover, depending on where the scar is located, the tattoo can produce mild to mind-numbing pain. It is also believed that deeper and bigger scars hurt the most, especially if they are located in places where the nerve damage is pretty serious. Smaller and more superficial scars don’t hurt as much because the skin is flat and the nerve damage is little.