dipsy, n.¹ — Green’s Dictionary of Slang

dipsy n.¹

[? abbr. SE dipsomaniac, i.e. a drunkard will receive a relatively short sentence]

(US tramp) a sentence to time in the workhouse; thus the individual sentenced (see cit. 1950).

1926		N. Klein ‘Hobo Lingo’ in AS I:12 651: Dipsy — workhouse sentence.
1930		‘Dean Stiff’ Milk and Honey Route 204: Dipsy – Workhouse sentence.
1950		Goldin et al. DAUL 59/1: Dipsy. (In many county jails) One sentenced to a workhouse term as differentiated from those awaiting serious charges.