Sassoon arrived at Craiglockhart on 23 July 1917, roughly one month after Wilfred Owen. He judged it to be 'a gloomy cavernous place even on a fine July afternoon', and nicknamed it 'Dottyville'. Although his initial impression was not too favourable, Craiglockhart provided Sassoon with an environment in which he could find respite from the anxieties of war. He would spend hours going for walks on the nearby Pentland Hills and playing golf on the local courses. There was little discipline within the hospital and the Director of Medical Services was said to have been shocked that officers were seen walking around the hospital in their slippers. Sassoon also found a friend in the distinguished psychologist Dr W H R Rivers who worked at this time at Craiglockhart and who was charged with 'curing' Sassoon.
Within a week of arriving at Craiglockhart, Rivers decided that Sassoon did not need to be 'cured'. Despite this assessment he continued to see his patient three times a week. It was his belief that as an officer in the Royal Army Medical Corps he had to return all healthy men to duty, yet the time he spent with Sassoon ensured that his own beliefs on the war and the effect it had had on his patients radically altered. Sassoon and Rivers were to become great friends and remained so until Rivers' death in 1922.