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@feditips
Are you aware of the performance cost of this? Backfilling a few hundreds message doesn't seems to be costly, in particular on single user instances, as they would be performed only occasionally.

I really appreciate the experience of backfilling in Synapse. (althought I'm not sure if it either try to backfill on the fly or if it sync the whole discussion in background after initial sync, which include the 20 last messages)