Taiwan Ecological Network (TEN) was introduced in 2018 as an island-wide cross-sectoral biodiversity-focused spatial planning strategy aimed at (I) restoration and support of resilient, biodiverse, connected, and well-functioning ecosystems within its 45 conservation corridors and (II) conservation and sustainable use of biodiversity in SEPLS and promotion of community resilience. Promotion of the Satoyama Initiative and landscape conservation makes up one of TEN’s strategic action tasks. Our study is a retrospective overview of how application of community-based resilience assessment workshops (RAWs) as a tool, operationalization of the integrated landscape–seascape approach (ILSA) in SEPLS as an approach, and their alignment with TEN as a strategy has helped to ensure and enhance connectivity within and across SEPLS over time. For our analysis, we employ a mixed-method, multilayered, and cross-temporal approach and look at the RAWs–ILSA–TEN processes (2018–2023) in four SEPLS (Fengnan, Xinshe, Gangkou, and Luoshan) located within two of TEN’s conservation corridors (the Xiuguluan River and the Northern Section of the Coastal Mountain Range) in Hualien County of eastern Chinese Taipei. We then discuss these processes from the perspective of the “tool–approach–strategy” bundle, multi-stakeholder interactions, and multiple meanings of connectivity in SEPLS, keeping in mind associated synergies and trade-offs. We conclude by outlining lessons learned and ways forward.