In a prospective cohort study of Veterans and community health nurses, we enrolled hospitalized older Veterans referred to home care for skilled nursing and/or physical or occupational therapy for posthospitalization care. We assessed preadmission activities of daily living and instrumental activities of daily living, health literacy, numeracy, and cognition. Postdischarge phone calls identified medication errors and medication reconciliation efforts by home healthcare clinicians. Veterans Administration-based community health nurses completed surveys about content and timing of postdischarge interactions with home healthcare clinicians. We determined the types and frequency of medication errors among older Veterans receiving home healthcare, patient–provider communication patterns in this setting, and patient characteristics affecting medication error rates. Most Veterans (24/30, 80%) had at least one discordant medication, and only one noted that errors were identified and resolved. Veterans were asked about medications in the home healthcare setting, but far fewer were questioned about medication-taking details, adherence, and as-needed or nonoral medications. Higher numeracy was associated with fewer errors. Veterans Administration community health nurses reported contact by home healthcare clinicians in 41% of cases (7/17). Given the high rate of medication errors discovered, future work should focus on implementing best practices for medication review in this setting, as well as documenting barriers/facilitators of patient–provider communication.