This paper asks the question: Is now the right time to consider a statewide policy initiative to support increased access for Massachusetts community college students to paid internships that can help them improve their employment and earnings trajectory? Is this something that employers, colleges, and state leaders would see as a welcome component of a comprehensive approach to strengthening the state's talent pipeline and reducing inequities in access to good jobs? The authors approach this important question in several steps. First, they report on the experience in Massachusetts and other states in designing and implementing paid internship programs for two- and four-year college students. There is some exciting experience with such initiatives around the country and in Massachusetts state, though programs for students at four-year schools tend to dominate. The report describes each program and summarizes its design, scale, and impact. Each description ends with key takeaways from the program about design, implementation, and cost. The authors draw out lessons about how to: (1) target a statewide program (by region, sector, and population); (2) organize the business community to participate and level-set their expectations about intern capabilities; (3) design programs that meet community college students where they are and accommodate their needs for income, transportation help, and work readiness support; (4) strengthen regional and college capacity to organize and manage a large-scale internship program; and (5) combine online technology and human outreach to improve the matches between potential internships and interested students. The authors interviewed more than two dozen leaders from business, the community colleges, state government, and students. They asked them whether they thought a paid internship initiative could help solve some of the problems they and their peers were facing. Although their answers reflect their own personal views and cannot be interpreted as representative, their enthusiasms and concerns paint a fairly clear picture of design priorities and pitfalls to avoid.