fix(server): wake milestones when interactions replace older cards

Co-Authored-By: Paperclip <noreply@paperclip.ing>

doc/plans/2026-10-24-recurring-server-sleep-stack.md

@@ -1496,3 +1496,11 @@ producer regressions failed before the added intent signals. All 169 cases acros
 the worker and interaction-service suites pass, as does production server
 typechecking. The draft remains incomplete: other producers and production
 registration/polling removal are still pending. See the milestone audit for logs.
+
+
+Slice 28 creation/sibling replacement now registers intent before the first
+interaction write. Both question and confirmation replacement failed before the
+fix; all 184 milestone/integration/unit interaction cases and production server
+typechecking pass. Remaining terminal-interaction writers are document-target
+expiry, deleted-addressee cancellation and startup supersession; other producer
+audits and production migration remain pending.

doc/plans/2026-10-25-chat-run-milestone-sleep-audit.md

@@ -809,3 +809,34 @@ Remaining interaction producers include document-target invalidation, deleted
 addressees, startup supersession and creation/replacement. Provider receipt,
 conversation/configuration and alternate recovery audits also remain. Production
 worker registration and lifecycle polling removal are still intentionally pending.
+
+
+## Creation and sibling replacement
+
+Creating a question or confirmation can expire a prior card from the same agent,
+release the prior run's provider response slot, and cancel its unsent prompt.
+The creation transaction now registers a single issue-scoped milestone intent
+before inserting the new row. This precedes both sibling invalidation and prompt
+publication changes. Existing idempotent reuse and validation return/throw before
+this boundary; unrelated interaction kinds remain outside it. Provider policy
+and sibling-supersession semantics are unchanged.
+
+The replacement regressions create two runs before worker startup, suppress the
+older failed run with its pending card, let the worker become quiet, then create
+the replacement through the actual service. They verify that the old card is
+expired and its failure notice appears without another run transition or poll.
+
+- `/tmp/sleep28-interaction-replacement-before.log`: question and confirmation
+  replacement both fail the missing-notice assertion before the creation signal.
+- `/tmp/sleep28-interaction-replacement-tests.log`: all 184 cases pass across
+  the 65 milestone worker, 106 interaction-service integration and 13 interaction
+  service unit cases. PostgreSQL suites use separate isolated databases.
+- `/tmp/sleep28-interaction-replacement-typecheck.log`: production server
+  typecheck passes; test files are excluded. `git diff --check` passes.
+
+The remaining direct terminal-interaction writers are document-target expiry
+(the resolution-time helper and explicit document-change method), deletion of
+an addressed agent, and startup supersession. Document-change callers are in
+`routes/issues.ts`; the owning state mutation is in the interaction service.
+Audit those before removing the lifecycle poll. This checkpoint still does not
+register the worker in production or establish final CI/review acceptance.

server/src/__tests__/chat-run-milestone-work.test.ts

@@ -640,20 +640,23 @@ const support = external ? { supported: true } : await getEmbeddedPostgresTestSu
     ["confirmation", "withdraw"], ["confirmation", "expire"],
     ["question", "comment"], ["question", "historical comment"],
     ["confirmation", "comment"], ["confirmation", "historical comment"],
+    ["question", "replacement"], ["confirmation", "replacement"],
   ] as const)("rechecks an unsent %s after %s", async (kind, action) => {
     const source = await run(f, { status: "failed", errorCode: "test_run_failed" });
     const interactions = issueThreadInteractionService(db);
     const issue = { id: f.issueId, companyId: f.companyId, status: "in_progress" };
-    const interaction = await interactions.create(issue, kind === "confirmation" ? {
-      kind: "request_confirmation", continuationPolicy: "wake_assignee", sourceRunId: source.id,
+    const createInteraction = (sourceRunId: string) => interactions.create(issue, kind === "confirmation" ? {
+      kind: "request_confirmation", continuationPolicy: "wake_assignee", sourceRunId,
       title: "Confirm", payload: { version: 1, prompt: "Continue?", supersedeOnUserComment: true },
     } : {
-      kind: "ask_user_questions", continuationPolicy: "wake_assignee", sourceRunId: source.id,
+      kind: "ask_user_questions", continuationPolicy: "wake_assignee", sourceRunId,
       title: "Choose", payload: { version: 1, title: "Choose", supersedeOnUserComment: true, questions: [{
         id: "choice", prompt: "Continue?", selectionMode: "single", required: true,
         options: [{ id: "yes", label: "Yes" }],
       }] },
-    }, { agentId: f.agentId, runId: source.id });
+    }, { agentId: f.agentId, runId: sourceRunId });
+    const interaction = await createInteraction(source.id);
+    const replacement = action === "replacement" ? await run() : null;
     if (action === "historical answer") {
       await interactions.dismissInteraction(issue, interaction.id, { userId: f.userId });
       await db.update(issues).set({ status: "done" }).where(eq(issues.id, f.issueId));
@@ -661,7 +664,10 @@ const support = external ? { supported: true } : await getEmbeddedPostgresTestSu
     await start(); await flush();
     expect((await publications()).some(row => row.idempotencyKey.startsWith(`run:${source.id}:`))).toBe(false);
     await quiet();
-    if (action === "comment" || action === "historical comment") {
+    if (action === "replacement") {
+      await createInteraction(replacement!.id);
+      expect((await db.select().from(issueThreadInteractions).where(eq(issueThreadInteractions.id, interaction.id)))[0].status).toBe("expired");
+    } else if (action === "comment" || action === "historical comment") {
       const [comment] = await db.insert(issueComments).values({ companyId: f.companyId, issueId: f.issueId,
         authorType: "user", authorUserId: f.userId, origin: "comment", body: "Ignore the earlier request" }).returning();
       const expired = action === "comment"

server/src/services/issue-thread-interactions.ts

@@ -3697,6 +3697,9 @@ export function issueThreadInteractionService(
                 eq(chatVoiceSessions.callerAuthority, "guest_intake"))).limit(1);
             if (guest) throw unprocessable("Ask this unverified caller a clarification in a task comment; submit_request will deliver their spoken follow-up. Protected human-input questions require authenticated access.", {code: "voice_guest_use_task_comment"});
           }
+          if (data.kind === "ask_user_questions" || data.kind === "request_confirmation") {
+            await notifyChatRunMilestones(tx, { companyId: issue.companyId, issueId: issue.id });
+          }
           const [row] = await tx
             .insert(issueThreadInteractions)
             .values({