For enlisted men entertainment on the isolated post was less picturesque than for the officers, but far more colorful.  As with most military bases of the time, a string of gin mills and bordellos grew up just the other side of the fort boundary near a site today called Black Butte.  The little community of Cypress, as it was known then, is said to have consisted of 32 saloons and two bordellos.

It was not a mixture that boded well for the lonely and bored soldiers stationed at Fort Assinniboine.  Trouble was sure to follow and often did.  Boredom and tedium at such an isolated site forced many to seek comfort in a bottle of red eye or the arms of a woman of easy virtue.   It also combined to promote an extraordinarily high rate of desertion and other disciplinary problems.  To deal with the problem a guardhouse capable of housing up to two dozen prisoners at a time was constructed on the south end of Fort Assinniboine next to the firehouse.

Efforts to combat boredom, desertion and drunkenness included such things as boxing matches and the construction of a post library. Located on the south end of the parade grounds.  It's not known how much the library was used or whether it was successful in diverting the soldiers’ attention away from the gin mills.  It was, however, a unique feature for a western military post of that time.