Green’s Dictionary of Slang

jail v.

(US) to spend time in prison, spec. to create the best possible situation for oneself given the overriding circumstances; usu. as jailing n.

[US]M. Braly On the Yard (2002) 4: He had been jailing for thirty of his forty-five years and was now a five-time loser.
[US]Simon & Burns Corner (1998) 62: They could jail if they had to, but tried their damnedest to stay out of the cuffs.
[US]Simon & Burns ‘Old Cases’ Wire ser. 1 ep. 4 [TV script] Bird jailed with Omar down in the cut.
[US]G. Pelecanos Drama City 191: It’s harder in some way to do your straight time than it is to jail.
[US]G. Hayward Corruption Officer [ebk] cap. 22: It’s all good, C.O. ’cause I jails for real. Ain’t no snitching here.

In derivatives

jailed (adj.)

1. (US teen) in a steady relationship.

[US]Summerfield Sun (KS) 9 Jan. 2/3: Teen Talk Glossary [...] Jailed — Going steady.
jailer (n.)

2. a regular prisoner who from repeated sentences has become habituated to the system.

[US]G. Hayward Corruption Officer [ebook] Ch. 18: I wasn’t worried about how Biz was going to answer the questions [...] of how this happened either because he’s a jailer. He’s someone who has been coming back and forth through the system for a minute so he knows the ‘I slipped and fell in the shower’ routine.