Damon only escapes after finally submitting to his pain and expressing genuine remorse to a vision of his dying mother.
Each time the loop resets, the situation grows darker. Damon initially believes he can "solve" the loop by being a hero, but the Stone reveals that his true torment is his repressed guilt regarding his mother, Lily. [S7E10] Hell Is Other People
"The Vampire Diaries" Hell Is Other People (TV Episode 2016) Damon only escapes after finally submitting to his
Damon is repeatedly sent back to a traumatic day during the Civil War in 1863, where he was tasked with capturing a group of deserters. [S7E10] Hell Is Other People