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## Stack context Follows #27495 (merged), which gives `chat_messages.id` an append-order guarantee and moves the history reads onto it. This PR applies the same fix to the query that builds the model prompt. ## Why? `GetChatMessagesForPromptByChatID` mixed two orderings. It selected the compaction boundary with `created_at DESC, id DESC`, then applied that boundary with an `id >` comparison, and returned rows with `created_at ASC, id ASC`. `created_at` is `now()`, so it is the transaction start time. Every row in one insert batch shares it, and concurrent transactions can commit in the opposite order to the one they started in. Two consequences, both reaching the provider: - **Malformed prompts.** A tool result could be ordered ahead of the assistant message that requested it. `chatprompt.injectMissingToolResults` does not repair this: it only handles tool rows already contiguous after an assistant row, and adds missing results. It never moves a tool row that precedes its assistant, and nothing re-sorts the rows in Go. - **Wrong compaction boundary.** The boundary is picked by timestamp but compared by id, so a stale compressed summary could be retained while the actual latest one was dropped. ## Changes Both the boundary CTE and the outer query order by `id`. The `id >` predicate is unchanged, which is the point: the ordering now matches the comparison that was always being made. **The boundary index was dead, so it is rebuilt to match.** `idx_chat_messages_compressed_summary_boundary` was created for exactly this lookup, but its predicate requires `role = 'system'` while compaction writes its summary with the user role (`message_conversion.go:334`, the only writer of `compressed = true`). It matched zero rows, and no other query can use it. Migration `000560` rebuilds it as `(chat_id, id DESC) WHERE compressed AND NOT deleted AND visibility = 'model'`, which also matches the new order key. Measured on PostgreSQL 13 with a 20k-message chat, 11 summaries, and 14 sibling chats so `chat_id` is selective: | boundary lookup | plan | buffers | |---|---|---| | old predicate | Index Scan `idx_chat_messages_chat`, 19,989 rows filtered | 267 | | rebuilt index | Index Only Scan | 2 | Not in scope: the outer `SELECT` still inspects every row of the chat, because its `role = 'system' AND compressed = FALSE` disjunct has no lower `id` bound. That predates this PR and needs a query rewrite rather than an index. ## Testing Two subtests, both verified red by reverting the `ORDER BY` and regenerating: - `OrdersByIDWhenTimestampsDisagree` returned `[4,3,2,1]` instead of `[1,2,3,4]`, placing the tool result before the assistant call. - `CompactionBoundaryUsesID` selected the stale summary and leaked the messages between the two summaries into the prompt. Existing subtests pass unchanged. Migration up/down tests pass, and the rebuilt index was verified red-green: restoring the old predicate returns the plan to a 267-buffer scan, and the old predicate matches 0 rows in the fixture. > Opened by Mux on behalf of Mike.