The lack of strict focus in the minimum-security environment worked to the advantage of some inmates who hoped to make a break for freedom. Most prisoners never made it to the mainland and more commonly turned back to be rescued. Those who were not missed and failed to turn back would eventually tire and drown. The prison did not start to utilize trained military prison guards until 1907, and up to that point inmates were usually guarded by young garrison soldiers, which sometimes provided seasoned prisoners with valuable opportunities. For this reason, there were numerous escapes during the military era.

In August of 1898, four young soldiers serving time for minor crimes escaped from the prison library and stole a rowboat that was tied under the wharf. The inmates ultimately reached the mainland, but not before one of them had been wounded by a garrison soldier who was on guard at the military wharf. The inmates were able to paddle a considerable distance out, but when one of them missed a stroke, the splash attracted the sentry's attention. The soldier opened fire on the inmates and hit one of them, who dropped into the bottom of the boat screaming and moaning in pain. Another of the inmates stood up and shouted to the soldier, “Don't shoot anymore. Don't you see we've got no oars? We surrender!”  The sentry stopped firing and briefly left his post to get assistance. Having succeeded with their clever ruse, the prisoners quickly pulled out their oars and rowed towards the mainland. A prison break alarm was sounded and the island’s five-oared boat was launched. The guards gave chase, but in spite of their best efforts, the prisoners got away. In another incident in 1884, two inmates stole a boat and rowed against the currents to the Marin shores. A sentry spotted the escapees but didn’t shoot and the inmates made a successful getaway.

In June of 1900 two inmates worked themselves through a chimney, and using a large section of lumber boarding as a float, they attempted to swim to the mainland. However, they got caught in a whirlpool and remained clinging to the log until they were rescued. In one example of remarkable ingenuity, four prisoners attempted to use a large butter vat as a boat and struggled to paddle the unstable vessel to the San Francisco shore. They were promptly captured when the currents proved too fierce. Other escape attempts involved forgeries of orders, disguises and cutting of bars. Several shooting deaths also resulted from attempted prison breaks. Each of these attempts displayed a certain amount of courage and desperation, coupled with the ingenuity born of constant contemplation under long years in confinement. The obsession of escaping Alcatraz was continuously evident throughout the prison’s history.

One of the more interesting escape-related incidents occurred in the fall of 1926, when a crowd of inmates allegedly plotted a mass prison break. Colonel G. Maury Crallé had recently taken over as Commandant of the Disciplinary Barracks, when rumors began to circulate among the military guards about the mammoth plot.  The alleged plan was for all of the inmates who were at work outside of the cellhouse perimeter to rush on signal toward the water’s edge, and swim for San Francisco. From the prisoners’ viewpoint, the scheme had considerable merit, but Colonel Crallé made the decision to address the inmates before they could attempt any such action. He called all of the inmates working on the labor details into the parade ground area and stood with his back to San Francisco. None of the officers were armed, and Crallé spoke to the men in a soft tone. He explained that he had been made aware of a mass escape plot and he expressed his opinion of such a foolish strategy. “ GO AHEAD, SWIM!” he challenged, giving no indication that he would attempt to stop those who tried. He dared the men to make a run for the water and assured them that there would be no pursuit. However, he did calmly mention the hungry sharks that would surely attack the large groups of swimmers... and without a single incident; the inmates went back to work.

Colonel G. Maury Crallé.

Perhaps one of the best descriptions of the Military Prison was written in a presentation entitled: Definition and Operationby Major W.R. Stewart in 1930. Stewart wrote in part:

The mission of the United States Disciplinary Barracks is two-fold. First, rehabilitative, and second, punitive. Punishment by confinement at hard labor is not the paramount aim of such institutions. The reclamation of the convicted soldier for the Army and society is of equal importance... The Pacific Branch of the United States Disciplinary Barracks is located on Alcatraz Island in San Francisco Bay. Here, on this little island, some 600 soldiers are expiating their crimes. Their sentences range from six months to life imprisonment. Approximately 10 percent of them are serving sentences of ten years or more. Over one-third have been sentenced for military offenses, the remainder for misdemeanors and felonies.

The prisoners at this institution are subjected to a firm, impartial discipline. Misconduct and misbehavior result in punishment, good conduct is rewarded. The punishments are not cruel but consist of forfeiture of good conduct time, loss of privileges, and solitary confinement for a limited period. The punishment is made to fit the offense and for minor infractions of rules may be only a reprimand or the loss of one or more entertainments. Every infraction is recorded for each prisoner and this record is considered in making work assignments and in taking action on requests for parole, clemency, or restoration.

All men in good standing – over 90% of the inmates of the institution - are granted all of the privileges allowed by law. Such men are permitted to attend all entertainments, including motion pictures, boxing bouts and shows provided by theatrical organizations of San Francisco and vicinity. They are permitted to write at least two letters weekly, with writing materials and stamps furnished by the government. They are issued tobacco with liberal smoking privileges. A well-stocked library is open to them. When not at work in the daytime they are allowed the freedom of the jail yard for exercise and games. Once a week all men in good standing are permitted to have visitors. Misconduct results in the loss of all privileges for stated periods, in the most refractory cases.

The spiritual welfare of the inmates of this institution is the charge of an Army chaplain detailed for this purpose. He holds regular services, teaches Bible classes and is the friend and advisor of all. It is also his duty to provide materials for sports and to provide and supervise entertainment...

The living conditions at Alcatraz are not uncomfortable, to say the least. The prison proper is considered to be a model in cleanliness, orderliness, and sanitation. The entire 600 prisoners housed in one great cell room, well lighted and ventilated. Each man has his own private cell, completely equipped. Every necessity is furnished to him. He wears a neat black uniform. His food is that of a soldier of the United States Army, the best fed of all the armies. The prisoner’s laundry and dry cleaning are done for him. A sanitary barbershop and baths are open to him daily. And, finally, a well-stocked storeroom is at his service from which he draws, as needed, everything from a toothbrush to a uniform.

Every opportunity possible is afforded the ambitious man for study. Illiterates must attend school daily. For others there is a night school. Many are taking correspondence courses or devoting their evenings to self-study. The prison library has a large and varied selection of technical works. Study is encouraged to the fullest extent possible.