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The Prison to Homelessness Pipeline: Why Formerly Incarcerated Men End Up on the Streets

Last Updated: January 2025 | 14 min read

A man serves his time, completes his sentence, and walks out of prison. He has paid his debt to society. Now what? For hundreds of thousands of Americans each year, the answer is homelessness. Formerly incarcerated people are ten times more likely to experience homelessness than the general population. In Tulsa's 2025 Point-in-Time count, 56% of people experiencing homelessness reported a history of justice system involvement. This is not coincidence. It is the predictable result of systems designed to exclude.

The Numbers Tell the Story

According to research from the Prison Policy Initiative, formerly incarcerated people experience homelessness at a rate of approximately 203 per 10,000, compared to about 20 per 10,000 in the general population. That tenfold increase represents hundreds of thousands of people cycling between incarceration and the streets.

The connection flows both directions:

  • 15% of people entering jails report being homeless in the year before their arrest
  • People released from prison are immediately homeless at rates up to 30% in some jurisdictions
  • Homelessness dramatically increases the likelihood of re-arrest and reincarceration
  • The median annual income for formerly incarcerated people is $10,090, far below what housing requires

Men are disproportionately affected because men are incarcerated at roughly 10 times the rate of women. The prison system is predominantly male, which means the prison-to-homelessness pipeline is predominantly male.

Why Release Leads to Homelessness

The barriers between prison and stable housing are numerous and reinforcing. Understanding them helps explain why so many men end up on the streets after release.

Immediate Release Challenges

When someone is released from prison, they often have:

  • No money or minimal gate money (typically $25-200)
  • No valid identification (IDs often expire during incarceration)
  • No phone or way to contact potential employers
  • No transportation
  • Clothes that may be years out of date
  • No housing lined up

Many are released in the middle of the night or early morning when services are closed. Some are released in locations far from where they have any connections. The system seems designed to ensure failure.

The Background Check Wall

Even when someone has the resources to seek housing, they face systematic exclusion. Background checks have become standard for virtually all rental housing, and a criminal record is grounds for denial.

The exclusion includes:

  • Private landlords: Most will not rent to anyone with a felony conviction
  • Public housing: Federal law allows (and sometimes requires) exclusion based on criminal history
  • Housing vouchers: Section 8 has mandatory and discretionary exclusions for criminal records
  • Family housing: Living with family in subsidized housing can jeopardize their lease

Some jurisdictions have passed "ban the box" legislation or fair chance housing policies, but enforcement is weak and the culture of exclusion persists.

Employment Barriers

Without income, housing is impossible. But employment faces similar barriers:

  • Background checks exclude felons from most formal employment
  • Professional licenses are often revoked or denied based on criminal history
  • Gaps in employment history are difficult to explain
  • Skills learned before incarceration may be obsolete
  • Without an address, many applications cannot be completed

The result is that many formerly incarcerated people can only access day labor, cash work, or employment in industries with minimal screening. These jobs rarely pay enough to afford housing at market rates.

Destroyed Social Networks

Incarceration destroys relationships. A man who goes to prison for several years may find when he returns that:

  • His marriage has ended
  • His children have grown up without him
  • Friends have moved on
  • Family members have died or become estranged
  • His community has changed beyond recognition

The informal support systems that help most people through housing crises simply do not exist for many returning citizens. There is no couch to crash on, no family to take them in while they get back on their feet.

Parole and Probation Complications

The supervision system intended to support successful reentry often creates additional barriers to housing:

  • Address requirements: Parole requires a valid address, but you cannot get housing without passing background checks
  • Geographic restrictions: Conditions may prohibit living in certain areas, limiting already scarce options
  • Association restrictions: Cannot live with other people with felony convictions, eliminating some affordable shared housing
  • Technical violations: Homelessness itself can lead to violation of parole conditions, resulting in reincarceration

The cruel irony is that housing instability is one of the strongest predictors of recidivism, yet the parole system often makes housing harder to obtain.

Mental Health and Substance Use

Incarceration often worsens the mental health and substance use issues that may have contributed to criminal behavior in the first place:

  • Prison is traumatic, creating or worsening PTSD
  • Mental health treatment in prison is often inadequate
  • Medications may be discontinued upon release
  • Substance use disorder treatment, if provided, rarely includes adequate aftercare planning
  • The stress of release and homelessness triggers relapse

The first two weeks after release are the highest risk period for overdose death, partly because tolerance has decreased during incarceration but also because of the overwhelming stress of navigating release with no support.

The Revolving Door

Homelessness after release dramatically increases the likelihood of returning to prison:

  • Survival crimes (theft, trespassing) become necessary
  • Without stable housing, avoiding negative influences is nearly impossible
  • Parole conditions cannot be met without an address
  • Mental health and addiction worsen on the streets
  • Police contact increases dramatically for homeless individuals

Studies show that stable housing after release reduces recidivism by 13% or more. Yet we continue to release people into homelessness and act surprised when they return to prison.

The cost of this cycle is staggering. Incarceration costs $35,000-60,000 per year per person. Chronic homelessness costs $30,000-50,000 per year in emergency services. Permanent supportive housing costs $12,000-15,000 per year. We are spending the most to achieve the worst outcomes.

What Actually Works

Breaking the prison-to-homelessness pipeline requires intervention at multiple points:

Pre-Release Planning

Effective reentry begins months before release, not the day someone walks out the gate:

  • Housing placement should be secured before release
  • Identification should be obtained while incarcerated
  • Benefits applications should be submitted prior to release
  • Mental health and substance use treatment should have continuity plans
  • Job training and placement should begin before release

Transitional Housing

Dedicated housing for people exiting incarceration provides the stability needed for successful reentry:

  • Immediate housing upon release eliminates the initial crisis
  • On-site services address employment, mental health, and addiction
  • Graduated independence builds skills for permanent housing
  • Community of others facing similar challenges provides peer support

Employment Programs

Without income, housing is impossible. Effective programs:

  • Partner with employers willing to hire people with records
  • Provide job training in fields with demand and living wages
  • Address practical barriers like transportation and work clothes
  • Offer ongoing support after placement

Policy Reform

Systemic change requires addressing the policies that create barriers:

  • Fair chance housing policies that limit use of criminal history in screening
  • Reform of public housing exclusions
  • Expansion of record sealing and expungement
  • Pre-release Medicaid enrollment
  • Parole reform to eliminate housing-related technical violations

Our Approach at The Steady Ground

Many of the men we serve have histories of incarceration. Our program is designed to address the specific challenges they face:

  • Long-term residential program that provides stability during transition
  • Comprehensive assessment through the Stronghold Assessment identifies specific needs
  • Job training and placement with partner employers
  • Mental health and addiction treatment on site
  • Help obtaining identification and clearing barriers
  • Graduated housing that builds toward independent living
  • Community and brotherhood that provides ongoing support

We believe that a man who has served his time deserves a real chance to rebuild. The current system does not provide that chance. We intend to.

The prison-to-homelessness pipeline is not inevitable. It is a policy choice. We choose to exclude people with criminal records from housing. We choose to release people with nothing. We choose to prioritize punishment over restoration. Different choices would yield different results. The men cycling between prison and the streets are not beyond help. They are beyond our current willingness to help. That can change.