Objective We evaluated nursing-related free-text communication orders to identify potential safety hazards and describe patterns and scope of care domains addressed that may reveal preventable workarounds and potential gaps in electronic health record (EHR) functionality. Materials and Methods A retrospective analysis of free-text EHR-based communication orders sent to or by nurses providing inpatient care at a major academic health system. Using built-in EHR tools and selection criteria, 13 193 orders were extracted, including 1373 unique orders. Using the Clinical Care Classification system standardized framework, we classified content by care domain and identified unique requests within each order. We reviewed each order for error-prone textual features based on standard patient safety guidance. We describe the distribution of domains, co-occurrence when 2 domains were present, and common patterns. Results The 1373 unique orders included a single request (65.3%), 2 requests related to 1 or 2 domains (19%), or 3 or more requests (15.7%). No orders included terms on the Joint Commission’s “Do Not Use” list. However, 13.6% of unique orders, and 16.7% of those related to medications, included error-prone symbols or abbreviations according to Institute for Safe Medication Practices guidance. Order content spanned 20 different care components but physical regulation, fluid volume, nutritional, safety, and medication were most frequently identified as single or co-occurring topics. Patterns were heterogenous. Discussion Free-text communication orders reveal workarounds, responses to upstream workarounds, and design constraints that should be further investigated. Remediation strategies are needed to reduce safety hazards and workflow impediments. Conclusions Analysis of free-text communication orders revealed opportunities for improvement.