Extension is known for creating educational environments conducive to the transformative learning required for people to change their perspectives and make better decisions in their lives. However, creating such environments is not easy. The complex Extension context often produces barriers to including program components that support transformative learning. Extension partnerships with nonprofits, government units, and businesses can reduce these barriers and enhance the potential for transformative learning by fostering caring program environments. A partnership between Extension and United Way exemplifies one model for developing programs focused on creating caring educational environments that encourage and sustain transformative learning.