These are the casings from 4 rounds I shot recently, in an old remington single shot, bolt action rifle.
They fired fine. The bolt would lift, but couldn’t be pulled back.
#1-2 had to tapped out with a ram. #3 was able to be extracted with a hard pull on the bolt.
#4, the short, extracted easily.
There is no visible damage in the barrel or anywhere else I can see, that causes/allows this to happen.