Designing meaningful technology-integrated learning remains a challenge for teachers. To address this problem, the purpose of this single case study was to examine how experts plan for technology integration. The conceptual framework of this study drew from information processing theory and combined two existing constructs: the notion of a problem space (Simon & Newell, 1971) with a process model of teacher planning (Yinger, 1980). The resulting combination was a new construct called the teacher planning problem space. The significance of this study was in the application of this new construct to focus on thoughts, decisions, and judgments of teachers during the planning process for technology integration. Participants included a purposeful sample of six technology-integrating experts designated as such by their distinction as the winners of an innovation award. Winning the award bounded the case and the unit of analysis was how each participant negotiated the teacher planning problem space. Data collection included a survey, interviews, audiovisual materials, and documents. Qualitative content analysis methods where used for interpreting data. Results indicated expert technology-integrating teachers continuously sought to improve instruction for their students and technology served to facilitate this goal. Learning from experience as well as knowledge of technology’s affordances were major contributors to these teachers’ flexibility, troubleshooting, and fearlessness when implementing innovative practices with technology. The teacher planning problem space model resulting from this study provides theoretical implications for examining teacher planning. Practical implications include suggestions for administrative policies regarding lesson plan requirements and planning strategies for integrate technology.