Green’s Dictionary of Slang

graduate v.

1. (US prison) to complete one’s sentence.

[US] ‘Jargon of the Und.’ in DN V 448: Graduate, To be released from prison after having served the sentence.
[US]Monteleone Criminal Sl. (rev. edn).
[US]A. Sample (con. late 1950s-early 1960s) Racehoss 230: Clemens, another all black unit, housed mostly first offenders. Many of us ‘graduated’ from there.

2. to increase, through knowledge and sophistication, one’s status within the ranks of one’s peers in the streets and the criminal milieu.

[US]R. Klein Jailhouse Jargon and Street Sl. [unpub. ms.].

3. (drugs) to stop using drugs altogether or to progress to stronger drugs.

[US]Illinois Legislative Investigating Committee Drug Crisis in Spears (1986).
[US]ONDCP Street Terms 11: Graduate — Completely stop using drugs; progress to stronger drugs.

In phrases

graduated in the schools (adj.)

(Aus. und.) educated in a reformatory.

[Aus]Crowe Aus. Sl. Dict. 33: Graduated in the Schools, brought up in the reformatory.