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This multiple case study sought to describe intergenerational learning (IGL) in the online teacher communities. More so, it disclosed into the online IGL’s directions of exchange, contents, strategies, and challenges. Data were gathered from 20 multigenerational teachers in the cases of a small and a big school for maximum variation, through semi-structured individual interviews and online interaction analyses. Results showed that online teacher communities through video conferences and group messaging pave the way for multigenerational colleagues in reference to age, period, cohort, and experience from learning from each other. Learnings of instrumental contents are embedded in multidirectional exchange, based on recognized expertise according to the younger generation’s cohort, and the older generation’s experiences. While varied contents from all generations find their way in the online teacher community, devaluing roles and contents could threaten the quality of teachers’ participation. Structured online learning activities however such Learning Action Cells (LAC) sessions could be instrumental to reinforce the valuing of varied roles and contents in the online IGL among teachers. Teachers learn during the structured sessions, they also learn equally valuable content in the flexible and spontaneous group messaging, although the latter is not a recognized form of professional learning. Keywords: professional learning, teachers, IGL, online learning, multiple case study