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+---
+name: "Matrix bot structured conversation history"
+---
+
+# Story 266: Matrix bot structured conversation history
+
+## User Story
+
+As a user chatting with the Matrix bot, I want it to remember and own its prior responses naturally, so that conversations feel like talking to one continuous entity rather than a new instance each message.
+
+## Problem
+
+The bot currently flattens per-room conversation history into a text prefix (`build_context_prefix`) prepended to each new message. Claude sees this as third-party context rather than its own prior responses, causing it to feel disconnected and not take ownership of things it previously said.
+
+Additionally, history is in-memory only (`HashMap` initialized on startup) — any server restart wipes all conversation state.
+
+## Acceptance Criteria
+
+- [ ] Conversation history is passed as structured API messages (user/assistant turns) rather than a flattened text prefix
+- [ ] Claude recognises its prior responses as its own, maintaining consistent personality across a conversation
+- [ ] Per-room history survives server restarts (persisted to disk or database)
+- [ ] Rolling window trimming still applies to keep context bounded
+- [ ] Multi-user rooms still attribute messages to the correct sender
+
+## Technical Notes
+
+- `build_context_prefix()` in `bot.rs` is the current flattening logic
+- The Claude API accepts a `messages` array with `role: "user"` / `role: "assistant"` — use this instead of text serialization
+- `ConversationHistory` type at line 58 of `bot.rs` already has the right structure, it just needs to be passed through properly
+- For persistence, consider SQLite (already a dependency via matrix-sdk) or simple JSON files per room
+
+## Out of Scope
+
+- Infinite history / summarization of old context
+- Cross-room memory