Web 2.0 technologies are designed to be open, flexible, and collaborative offering many tools to support traditional or non-traditional tele-mentoring activities. The benefit of effortless sharing and connectivity comes with challenges in how we view such things as ownership, privacy, and duplicity. The Web 2.0 toolkit includes applications for web-based note-taking, shared documents, feedback, reflection, informal discussion, and presentation. The collaborative opportunities provided by mashable, social networking platforms allow users to flex time, geography, and projects. Professional educators continue to inform their practice and explore new ways to meet the needs of students. Web 2.0 technologies can support educational professionals by opening doors and classrooms world-wide. The chapter makes a comparison between online and mentoring instructional practice and highlights models for educational use of and aids in identification of tools for mentors and mentees.