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feat(ingest): accept Hookdeck-forwarded deliveries, and reject stale inbound Linear events - #6799

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fix-linear-echo-race
Aug 23, 2026
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saddlepaddle merged 5 commits into
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fix-linear-echo-race

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@saddlepaddle saddlepaddle commented Aug 23, 2026 •

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Groundwork for routing webhook ingest through Hookdeck. Nothing here changes behaviour until a Hookdeck source actually exists — every delivery still arrives directly from the provider and verifies exactly as it does today.

Why

Hookdeck was chosen over building an ack-then-process gateway ourselves: at current volume it is roughly cost-neutral against the Vercel compute it displaces, and it buys burst absorption, retries, replay and a DLQ without a multi-week build. The full assessment is here.

Two things have to be true before any traffic moves, and both are in this PR.

1. Linear's ±60s replay window would reject every retry

parseVerifiedPayload hands Linear's webhookTimestamp to the SDK, which enforces Linear's ±60 second replay window. Hookdeck preserves the original provider signature and timestamp when it retries — so a delivery retried five minutes later arrives with a timestamp well outside the window and 401s permanently, on every attempt. The failure is silent, total, and lands precisely on the deliveries a gateway exists to save.

verifyHookdeckDelivery checks x-hookdeck-signature instead — HMAC-SHA256 over the raw body with no timestamp component, so it survives any delay. x-hookdeck-verified is checked alongside it and is not redundant: the signature proves Hookdeck sent the request, the flag proves Hookdeck authenticated the provider first. Without it, a source whose verification was never configured would forward whatever anyone posted to its URL, correctly signed and indistinguishable from real traffic.

GitHub needs no equivalent change — its signature covers no timestamp, so it already tolerates arbitrary retry latency. That makes it the right provider to pilot first.

2. The mirror applies stale inbound events

A write we push to Linear returns as a webhook and the mirror applies it unconditionally. This is not a reported failure and there is no evidence of it happening — the window is a second or two, and it is largely self-correcting because the second edit pushes too and its own echo repairs the damage.

But both of those protections are properties of low, ordered latency, which is exactly what a gateway removes. Queue depth widens the window to minutes on a retry, and at-least-once delivery makes reordering routine. The guard has to exist before deliveries can be delayed and reordered, not after.

Recording Linear's updatedAt on every outbound write and refusing anything not strictly newer covers the echo and the reordering with one comparison.

Verified

Provisioned a real Hookdeck source and pushed signed traffic through it rather than trusting the documentation:

  • x-github-delivery forwards byte-identical — the whole dedup story rests on this
  • a bad signature is rejected 401 at Hookdeck's edge
  • the forwarded delivery carries X-Hookdeck-Verified: true
  • recomputing HMAC-SHA256 over the raw body reproduced Hookdeck's X-Hookdeck-Signature exactly, and the real delivery passes end-to-end through the verifier

Also confirmed the rendered SQL for the conflict guard ("tasks"."external_updated_at" < excluded.external_updated_at, timestamps binding as ISO-8601 UTC) rather than assuming it.

Not covered

  • The migration has not been executed against a database — SQL rendered and inspected, not run
  • No Hookdeck source carries production traffic; the code path is inert until one does
  • HOOKDECK_SIGNING_SECRET is set from a trial project and must be rotated when a production project exists
  • Bounded retry for partial fan-out failure is still open — it should read Hookdeck's X-Hookdeck-Attempt-Count rather than our own retryCount

https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V


Summary by cubic

Accepts Hookdeck-forwarded Linear webhooks and rejects stale or echoed Linear events. Old: we revalidated Linear’s ±60s timestamped signature and applied every event; New: we accept x-hookdeck-signature plus x-hookdeck-verified (retry-safe), persist external_updated_at, ignore events not strictly newer, and gate outbound updates so the watermark only moves forward. Behavior is unchanged until traffic routes via Hookdeck.

  • Review/Rollout
    • Dual path stays live: if x-hookdeck-signature is absent, we verify Linear’s signature as before. Rollback is URL repoint only.
    • Set HOOKDECK_SIGNING_SECRET in each environment; workflows pass it through. Signed but unverified/mismatched Hookdeck deliveries 401.
    • Migration: run 0091_tasks_external_updated_at. Existing rows start null and adopt a watermark on their next event.
    • Linear sync records provider updatedAt on writes and webhooks; outbound updates only advance the watermark (null-or-strictly-older), and inbound upserts gate on recency via SQL setWhere. GitHub webhook behavior is unchanged.

Written for commit 3898a58. Summary will update on new commits.

Review in cubic

Summary by CodeRabbit

  • New Features

    • Added secure support for webhook deliveries routed through Hookdeck.
    • Linear task synchronization now tracks external update times.
    • Webhook processing filters stale, duplicate, and echoed updates to keep tasks current.
  • Bug Fixes

    • Improved Linear synchronization reliability for delayed or repeated webhook deliveries.
    • Preserved direct Linear webhook verification while supporting verified Hookdeck requests.
  • Security

    • Added HMAC-based validation and required verification checks for Hookdeck webhook traffic.
    • Enabled the signing secret for preview and production deployments.

Groundwork for putting a queue in front of this endpoint, not a fix for
a failure anyone has reported.

A write we push to Linear returns to us as a webhook, and the mirror
applies it unconditionally. Today that is close to harmless: the echo
only overwrites if a second edit lands in the second or two before it
arrives, and it is largely self-correcting, because that second edit
pushes too and its own echo repairs the damage moments later. The case
that does not self-correct — two echoes arriving out of order, the stale
one landing last — is rare enough over direct delivery that there is no
evidence of it happening.

Both of those protections are properties of low, ordered latency, and a
gateway removes them. Queue depth widens the window from seconds to
however far behind the consumer is, minutes on a retry, and at-least-once
delivery makes reordering routine rather than exceptional. The guard has
to exist before deliveries can be delayed and reordered, not after.

Records Linear's own updatedAt on every outbound write and refuses any
inbound event that is not strictly newer, which covers the echo and the
reordering with one comparison. Checked ahead of the branchName fetch so
a suppressed event costs no Linear API call, and again in the upsert's
setWhere, because that read can go stale before the write lands and two
deliveries for one issue can race. Compared column-to-column against
excluded rather than a bound parameter, so no second timestamp conversion
can disagree with the first.

Rows predating the column have a null watermark and are always applied,
so existing tasks adopt one on their next event.

Claude-Session: https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V
Adds verification for a Hookdeck-forwarded delivery and wires it into the
Linear webhook ahead of Linear's own check. Both paths stay live: anything
arriving without an x-hookdeck-signature verifies exactly as it did
before, so a cutover is repointing a URL and a rollback needs no deploy.

Linear is the route that needs this. Its signature covers a timestamp and
the SDK enforces Linear's ±60s replay window, while Hookdeck preserves the
original signature and timestamp when it retries — so re-checking Linear's
signature behind a queue would reject every retry, which is precisely the
delivery a gateway exists to save. Hookdeck's own signature is HMAC-SHA256
over the body alone and survives any delay. GitHub needs no equivalent
change: its signature covers no timestamp, so it already tolerates
arbitrary retry latency.

x-hookdeck-verified is checked alongside the signature and is not
redundant. The signature proves Hookdeck sent this; the flag proves
Hookdeck authenticated the provider before forwarding. Without it, a
source whose verification was never configured would hand us whatever
anyone posted to its URL, correctly signed by Hookdeck and
indistinguishable from real traffic.

The secret is optional so environments without Hookdeck keep booting, but
a signed delivery arriving somewhere it is unset is rejected rather than
trusted — the alternative is trusting a header anyone can send.

Claude-Session: https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V
GitHub Secrets are where runtime env originates in this repo — the deploy
workflows map them into the environment the Vercel CLI reads, so a
variable that is not listed here is never populated no matter what the
schema says. Without it the Hookdeck branch would be unreachable in every
environment and every delivery would quietly fall through to provider
verification, which is the failure that looks like nothing being wrong.

ci.yml needs no change: lint, typecheck and test never read it, and the
schema marks it optional so a build without it still succeeds.

Claude-Session: https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V
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📝 Walkthrough

Walkthrough

Linear webhook handling now supports verified Hookdeck deliveries and filters stale or echoed events by provider update time. Deployment workflows pass the Hookdeck secret, and the tasks schema stores the external timestamp.

Changes

Linear webhook synchronization

Layer / File(s) Summary
Hookdeck delivery authentication
.github/workflows/deploy-preview.yml, .github/workflows/deploy-production.yml, apps/api/src/env.ts, apps/api/src/lib/webhooks/hookdeck.ts, apps/api/src/lib/webhooks/verify.ts
The API verifies Hookdeck signatures and provider verification headers. Preview and production deployments pass HOOKDECK_SIGNING_SECRET to Vercel.
Task external timestamp persistence
packages/db/drizzle/0091_tasks_external_updated_at.sql, packages/db/drizzle/meta/_journal.json, packages/db/src/schema/schema.ts, apps/api/src/app/api/integrations/linear/jobs/sync-task/route.ts, apps/desktop/.../getSelectedTasks.test.ts
The tasks table stores nullable externalUpdatedAt values. Linear task creation and updates persist the issue updatedAt timestamp. The task fixture supplies the nullable field.
Webhook staleness control
apps/api/src/app/api/integrations/linear/webhook/route.ts
The webhook route accepts verified Hookdeck payloads, retains direct Linear signature validation, skips stale events, and conditionally upserts newer task data.

Estimated code review effort: 4 (Complex) | ~45 minutes

Merge Risk: 🟡 Moderate · up to 6e933

The PR adds stale-event protection, but outbound Linear task updates can still write timestamps without the same guard, allowing older task data to overwrite newer data when deliveries are reordered or retried. This bounded data-correctness issue should be fixed or explicitly accepted before merge.

Sequence Diagram(s)

sequenceDiagram
  participant Hookdeck
  participant LinearWebhook
  participant TasksDatabase
  Hookdeck->>LinearWebhook: Deliver verified Linear webhook
  LinearWebhook->>TasksDatabase: Read externalUpdatedAt
  TasksDatabase-->>LinearWebhook: Return stored timestamp
  LinearWebhook->>TasksDatabase: Upsert newer task state
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✅ Passed checks (5 passed)
Check name Status Explanation
Docstring Coverage ✅ Passed Docstring check was indeterminate for this PR — some files could not be analyzed in time. Not blocking.
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Out of Scope Changes check ✅ Passed Check skipped because no linked issues were found for this pull request.
Title check ✅ Passed The title uses conventional commit format and clearly describes the Hookdeck delivery and stale Linear event changes.
Description check ✅ Passed The description explains the changes, rationale, validation performed, rollout notes, and known limitations; its testing content is clearly provided under Verified.
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Actionable comments posted: 1

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Inline comments:
In `@apps/api/src/app/api/integrations/linear/jobs/sync-task/route.ts`:
- Line 164: Add a null-or-strictly-older externalUpdatedAt predicate to the
tasks update containing externalUpdatedAt, so it only writes when the existing
timestamp is null or older than the outbound response; otherwise leave the row
unchanged.
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  • apps/api/src/app/api/integrations/linear/webhook/route.ts
  • apps/api/src/env.ts
  • apps/api/src/lib/webhooks/hookdeck.ts
  • apps/api/src/lib/webhooks/verify.ts
  • packages/db/drizzle/0091_tasks_external_updated_at.sql
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🧹 Preview Cleanup Complete

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The fixture spells out every column of TaskWithStatus, so adding one to
the schema breaks it. Caught by CI rather than locally because the root
typecheck spans 37 packages and I had only run the two I touched.

Claude-Session: https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V
CodeRabbit caught a hole in the guard two commits back. The outbound
update wrote externalUpdatedAt unconditionally, so the watermark was not
actually monotonic and the inbound guard was only as good as the value it
compares against.

The push goes out through QStash and can be retried, so its response can
land after a webhook that already recorded something newer. Writing ours
unconditionally then drags the watermark backwards, and the next stale
delivery sails through the check that exists to stop it — the original bug,
reachable by a slightly longer route.

Gates the update on the same null-or-strictly-older predicate the inbound
upsert uses. Skipping the write costs nothing: the webhook that overtook us
already set lastSyncedAt and cleared syncError on its way past.

Left the create path alone. A task being pushed to Linear for the first
time has no watermark, so every write there is an increase, and gating it
would risk dropping the external id linkage for no gain.

Claude-Session: https://claude.ai/code/session_014D6wif8HDRCXEFf5Ku4w7V
@saddlepaddle

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Good catch on the outbound watermark — confirmed and fixed in
fix(linear): keep the outbound watermark moving forward only.

Verified the concern is reachable: syncTask publishes through QStash with retries, so the updateIssue response can land after a webhook has already committed a newer watermark. Writing unconditionally dragged it backwards and reopened the exact gap the inbound guard closes.

Gated the update on the same null-or-strictly-older predicate. Nothing is lost when it skips — the webhook that overtook it already set lastSyncedAt and cleared syncError.

Left the create path unguarded deliberately: a task pushed to Linear for the first time has no watermark, so every write there is an increase, and gating it would risk dropping the external id linkage for no benefit.

@saddlepaddle
saddlepaddle merged commit 0eb12e3 into main Aug 23, 2026
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@saddlepaddle
saddlepaddle deleted the fix-linear-echo-race branch August 23, 2026 21:41

This branch was previously deployed

1 inactive deployment
preview — 3898a58a Deployed Aug 23, 2026 by saddlepaddle via Deploy Web #8346
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