fix(server): persist hook chat messages at occurred_at so spool replays keep conversation order

[daviddanialy]

Summary

Fixes the out-of-order transcript rows after offline-spool recovery (DNO-536) at the root: the server now persists hook-captured chat messages at the event's original occurred_at, and transcript readers order by (created_at, seq). Arrival order no longer decides conversation order, so backlog replayed after a live event still sorts before it — and replayed rows now display their true timestamps instead of drain time.

This supersedes the client-side ordered-send-queue approach (#4275, closed unmerged): event-time ordering at the server covers every late-delivery path (spool replays, async hook races, retries) instead of best-effort sequencing at the sender.

Changes

• Ingest (server/internal/hooks/ingest_hooks.go): canonical conversation events persist canonicalEventTime(payload) as created_at, clamped to arrival time so a skewed device clock cannot sort a row into the future. The envelope already carried occurred_at; telemetry rows already trusted it — chat rows now do too.
• Readers (server/internal/chat/queries.sql): every transcript query — full lists, latest/explicit generation, keyset pages, risk/search windows, resolution boundaries — orders by (created_at, seq). seq stays the stable tiebreak.
• Cursors unchanged at the API: keyset pagination keeps its before_seq/after_seq int cursors; the anchor row's (created_at, seq) position is resolved server-side with a subselect, so pages agree with display order without any client/SDK change.
• Non-hook writers unchanged in behavior: playground, assistants, and imports leave created_at unset and ChatMessageWriter stamps each batch with one shared write-time value — rows tie on created_at and seq decides, preserving their exact previous ordering even when buffered rows are constructed out of order (pinned by the existing TestCaptureMessage_FlushesPendingRowsAtomically).

Tests

New TestIngest_ReplayedMessageSortsByOccurredAt drives the exact repro through the real handler + Postgres: a live event arrives first, an older replayed event arrives second, and ListChatMessages returns them in occurrence order with created_at carrying the original occurred_at; a future-dated event is clamped to arrival time. Full chat, hooks, assistants, risk, and risk_analysis suites pass, plus lint:server.

Notes

• No migration: created_at already exists; the copyfrom query now supplies it explicitly.
• Rows without an explicit timestamp are stamped by the writer, so nothing can insert a NULL/zero created_at.

🤖 Generated with Claude Code

---

Summary by cubic

Persist hook-captured chat messages at their original occurred_at (clamped to [now−14d, now]) and read transcripts by (created_at, seq) so spool replays keep the correct conversation order. Fixes Linear DNO-536 where newer live messages appeared before older replayed ones; chat list recency now reflects pure message time.

• Bug Fixes

  • Ingest: persist occurred_at as created_at via one canonical clamp (no future, no >14d past); missing/malformed occurred_at falls back to arrival; pass the resolved time into persistence so chat rows, telemetry, and enforcement share one event time; persist replayed.
  • Queries: order all transcript reads/windows by (created_at, seq); keyset pages resolve anchor position by (created_at, seq) within the same project/chat and fall back to plain seq if the anchor is missing; “latest user message” and resolution boundaries align to transcript order.
  • Writers: non-hook paths leave created_at unset; all inserts route through a single chokepoint that stamps one write-time per batch, preserving previous ordering when rows are constructed out of order.
  • Chat lists: recency uses message time only (no updated_at bump), so backlog-only replays keep their occurred-time position.

• Migration

  • No schema or API changes; seq-based cursors are unchanged.

^{Written for commit 581460b. Summary will update on new commits.}

[linear-code]

DNO-536

[changeset-bot]

🦋 Changeset detected

Latest commit: 581460b

The changes in this PR will be included in the next version bump.

This PR includes changesets to release 1 package

Name	Type
server	Patch

Not sure what this means? Click here to learn what changesets are.

Click here if you're a maintainer who wants to add another changeset to this PR

[cubic-dev-ai]

All reported issues were addressed across 16 files

<sub>Reply with feedback, questions, or to request a fix.

Fix all with cubic | Re-trigger cubic</sub>

[cubic-dev-ai]

All reported issues were addressed across 18 files (changes from recent commits).

<sub>Tip: Review your code locally with the cubic CLI to iterate faster.

Fix all with cubic | Re-trigger cubic</sub>