Jennifer Gonnerman closes Life on the Outside by recounting her subject’s recurring dream. In it, Elaine Bartlett returns triumphant, decked out in her finest outfit, to Bedford Hills Correctional Facility, where she was locked up for almost two decades. She’s swept through the building like a VIP and taken to a gathering at which she delivers a rousing speech against drug laws. “Remember when you used to look down your nose at me?” she admonishes her mythical audience. “Well, look at me now.”

Years after her release; after having successfully navigated high-stakes battles with her parole officers, her employers and her family; and after having developed an activist’s fame through news stories like those Gonnerman filed for the Village Voice, Bartlett’s highest hopes are still not centered in the free world but, rather, squarely inside Bedford Hills.

It’s the perfect coda to Bartlett’s biography, crystallizing the book’s primary theme: Once you go to prison, you never really leave.

Having spent her life’s formative years at Bedford, it is no surprise that Bartlett still views both her successes and failures through its frame. This is perhaps the most demoralizing aspect of the high incarceration rates and absurdly long prison sentences created by the Rockefeller drug laws: The imaginations of too many black New Yorkers are bound by the justice system.

Yet the world people face when they get out of prison is filled with other, more concrete obstacles. Gonnerman illustrates these legal and social landmines by deftly blending Bartlett’s personal journey with explanations of the policies that complicate ex-cons’ lives. She doesn’t divert the narrative into lengthy histories and analyses, but she does pause long enough to point out how and why policymakers carefully laid each of the traps Bartlett stumbles across–from those that landed her in prison in the first place, to those that keep her from leaving it behind.

Gonnerman begins with the chilling tale of Bartlett’s 1983 arrest in an Albany sting. Her case is extreme: She was set up by a drug-dealing police informant. Nonetheless, it illustrates the zeal with which cops, prosecutors and judges enforced the Rockefeller laws throughout the 1980s. When she was 25, Bartlett’s first offense–transporting coke from Harlem to Albany–got her 20-to-life.

One of the book’s most affecting passages juxtaposes Bartlett’s fate 17 years later with that of those who destroyed her life. After recounting Bartlett’s deliberately humble performance for a parole board in 1999, Gonnerman tells us that, by this point, the lead cop had become deputy superintendent of state police. The informant had been arrested for a later cocaine deal but was a savvy enough defendant to plead to a lesser charge and get a mere six years. (He later died of an overdose.) And the state’s annual prison budget had grown from $450 million when the Rockefeller laws passed in 1973 to $1.7 billion.

Bartlett’s notoriety as an inmate activist and her song and dance for the parole board got her onto Governor Pataki’s clemency list in 2000. But when she got home, she realized that much of her life was still governed by the criminal justice system.

Gonnerman focuses on Bartlett’s difficulty navigating parole. She illustrates how, ironically, the primary challenge isn’t the rules–curfews, travel restrictions, even bans on what sort of pets you can have–but the way they’re enforced. Your future depends largely on which parole officer you draw, and how that person chooses to wield the law.

Bartlett’s first P.O. was willing to loosen the rules to allow her space for rebuilding a life under difficult circumstances. He overlooked the occasional missed appointment and the chaos in the apartment she shared with an ever-changing array of family members. He relaxed the curfew so she could work a night shift, and let her blow off steam with harmless acts of rebellion. A later officer used a much different approach–shoving into the apartment in an effort to intimidate her and her family, escalating small arguments into threats of arrest, and generally daring Bartlett to screw up. Confronted with her own powerlessness, Bartlett reacted by picking fights with the officer, and nearly ended up back in prison.

Parole restrictions weren’t the only pitfall Bartlett needed to avoid; legislators and bureaucrats had deliberately limited her options. From employment to voting rights, ex-offenders face a series of legally sanctioned privacy invasions and restrictions on what help they can get. Perhaps the most frustrating barrier for Bartlett was the ban on former prisoners living in public housing. Since 1988, Congress has passed a series of laws authorizing and aiding local housing authorities in evicting people with criminal records; New York City aggressively enforced them.

Gonnerman also shows how the record of the state’s Urban Development Corporation added to Bartlett’s housing troubles during Governor Mario Cuomo’s administration. The UDC was set up in 1968 to build affordable housing; under Cuomo, between 1984 and 1989, the UDC spent 80 percent of the $1 billion in bonds it issued on prison construction.

With her housing options limited, Bartlett had to depend upon her daughter’s willingness to secretly put her up in a corner of a crowded projects apartment. That complicated the already precarious process of reviving relationships with children she hadn’t been around to raise. For all her legal troubles, this was the most difficult challenge of post-prison life for Bartlett. She desperately wanted to reconnect with her kids, but they only knew their mother as an idea, not a demanding physical presence.

Again, Gonnerman affectingly illustrates the disconnect. During one of the family’s many fights–this time over who would get to sleep in the largest bedroom–Bartlett’s teenaged daughter called the cops to report a domestic dispute. Bartlett knew the stakes: It could lead her back to jail, or at least make her parole officer tighten the rules. But as she read the police report, with her daughter’s name under “victim” and hers under “suspect,” she felt not fear but sadness. She understood how far apart they had grown during her lengthy prison sentence. And she realized that the freedom she had so longed for in prison had not yet come, because the distance prison created still held her family captive.