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).

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.