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Research, advocacy, and archival projects related to incarceration often lack knowledge about the ongoing conditions of county jails, and myriad challenges prevent stakeholders from successfully conducting outreach to people experiencing confinement in jails. Using a case study of archival materials contributed to PrisonPandemic, wherein we invited and accepted letters and phone calls from those incarcerated in California during the COVID-19 pandemic, we demonstrate a novel outreach method using web scraping and postal mailing. We analyze PrisonPandemic’s outreach, rejection rates, and response rates to 20 county jail systems during October to December 2021. We demonstrate that scraping and mailing helps overcome typical challenges associated with outreach to this population and can create a comprehensive sampling frame to achieve response rates comparable to that of traditional outreach methods to non-incarcerated populations. We also discuss the benefits, challenges, and ethical implications of using scraping and mailing.