It would appear that concessions granted to prisoners, and said prisoners taking advantage of lax jail procedures, are not confined to the modern day:

Daily Arkansas Gazette, Little Rock, Arkansas, Saturday, April 12, 1879
“I Go A Fishing”
How Two United States Prisoners Made Their Escape
Next in the walking mania is the prisoners-escaping fever. Prisoners all over the country are trying to get away, and the conclusion is that their quarters do not suit them. The following from the Fort Smith New Era is worth reading: “An event of a serio-comic nature which the United States Marshal’s office has been trying to keep dark, has just leaked out. About the 25th ult., two prisoners, G.T. Chase and Robert Bishop, both white and serving sentence for introducing whisky into the Indian Territory, were permitted, as often before, to go a fishing in Poteau River just back of the old garrison. Jailor Burns kindly provided the outfit. On that day, the two fishermen failed to make their appearance and report at the jail at the usual time. In fact, Chase and Bishop had crossed the river and were making tracks for freedom in Oklahoma. The story goes, that on the same day they were met by two deputy United States marshals returning to Fort Smith from a trip and who knew the escaped prisoners very well. The latter put a bold face on the matter and averred that their term of confinement had expired and actually begged for pecuniary assistance to help two poor unfortunates along in their struggle with a cruel world. Ed. Burns, one of the deputies, good naturedly gave seventy-five cents. When the officers reached Fort Smith and found out how they were duped, it is said they started in pursuit of the fugitives early next morning and overtook them. But in a fight which ensued, the prisoners escaped, after wounding one of the deputies, Dwight Wheeler, a brother of the United States clerk, Stephen Wheeler. We give the story as told to us. Of the truth of the escape of the prisoners there is no doubt.”