[11] Three founders, Dr. Charles Spray, Arnold Goldberg, and Mary Lu Zurcher founded Outside In in June 1968 and it was one of the earliest free clinics on the west coast.

[9][12][13] The organization was founded to serve Portland's "alienated youth", some of whom were illegal drug users and most had mental health issues.

[2][19] Willamette Week reported in April 2019 that Outside In employees are members of AFSCME along with a handful of other private nonprofits heavily funded by government contracts.

[20] In April 2019, Outside In announced the plan to add a second location in Gresham intended to provide services to "unique populations that are not well-served in other health care settings,".

[6] In 2023, the organization self reported it served 969 youth with mental health care, drug and alcohol treatment, employment, education, job training, and housing.

[26] The organization's harm reduction program has received over a million dollars from Measure 110 funding and an estimated 100 clients utilize it daily.

[27] After it started handing out smoking supplies in October 2022, its program manager reported this caused an 87% increase in monthly visit to the ham reduction services.

"Our neighborhood is also filled with bloody cotton balls and feces-covered wipes that were given out at Outside In," added the letter, which was signed by Tracy Prince, the league's vice chair.

[30] The harm reduction program's policy of prohibiting drug use within three blocks from facilities while handing out paraphernalia has drawn criticism from neighbors and businesses in October 2024.

[33] "Bespoke" is bicycle-powered smoothie cart set up in Portland's O'Bryant Square that gives homeless youth on-the-job training.