Background: Medicaid enrollment and retention among eligible populations remains a challenge. Purpose: We assessed health literacy-related features and content of Internet-based state Medicaid enrollment materials and resources. Methods: In February 2021, using established tools, we evaluated paper Medicaid enrollment applications and scope of enrollment resources (on-line enrollment option, toll-free telephone assistance, live chat function, instructional and/or informational audiovisuals). Results: Forty (78.4%) English- and 28 (54.9%) Spanish-language paper Medicaid enrollment applications were available. Overall, document complexity was high as a large volume of information is required to apply for Medicaid coverage. An on-line Medicaid enrollment option was nearly universal. Medicaid government platforms were more likely to provide toll-free telephone assistance (n = 34; 66.7%) than a live chat function (n = 10; 19.6%). Eleven (n = 11; 21.6%) government platforms provided an instructional and/or informational Medicaid enrollment audiovisual resource. Discussion: Our work suggests the need for states to leverage technology in creation of resources to match language and cultural needs of the diverse US population. Translation to Health Education Practice: Access to continuous health insurance coverage, comprehensive clinical care services, and evidence-based health education programming combined are essential in promoting both individual and community health.