fix(server): wake chat milestones on question claim transitions

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

server/src/services/question-response-delivery.ts

@@ -455,6 +455,9 @@ export function questionResponseDeliveryService(
         current.lastAttemptAt.getTime() > claimAt.getTime() - claimStaleMs
       )
         return null;
+      if (current.status !== "delivering") {
+        await notifyChatRunMilestones(tx, { companyId: current.companyId, issueId: current.issueId });
+      }
       return tx
         .update(issueQuestionResponseDeliveries)
         .set({
@@ -593,25 +596,28 @@ export function questionResponseDeliveryService(
     const nextErrorCount = delivery.errorCount + (options.bounded ? 1 : 0);
     const exhausted =
       options.bounded && nextErrorCount >= MAX_DELIVERY_ATTEMPTS;
-    await db
-      .update(issueQuestionResponseDeliveries)
-      .set({
-        // Keep an exhausted claim owned until recordTerminal commits its outcome.
-        status: exhausted ? "delivering" : "pending",
-        ...(options.bounded ? { errorCount: nextErrorCount } : {}),
-        lastErrorCode: errorCode,
-        updatedAt: at,
-      })
-      .where(
-        and(
-          eq(issueQuestionResponseDeliveries.id, delivery.id),
-          eq(issueQuestionResponseDeliveries.status, "delivering"),
-          eq(
-            issueQuestionResponseDeliveries.attemptCount,
-            delivery.attemptCount,
-          ),
-        ),
+    await db.transaction(async (tx) => {
+      const ownedClaim = and(
+        eq(issueQuestionResponseDeliveries.id, delivery.id),
+        eq(issueQuestionResponseDeliveries.status, "delivering"),
+        eq(issueQuestionResponseDeliveries.attemptCount, delivery.attemptCount),
       );
+      const [current] = await tx.select({ id: issueQuestionResponseDeliveries.id })
+        .from(issueQuestionResponseDeliveries).where(ownedClaim).for("update");
+      if (!current) return;
+      if (!exhausted) {
+        await notifyChatRunMilestones(tx, { companyId: delivery.companyId, issueId: delivery.issueId });
+      }
+      await tx.update(issueQuestionResponseDeliveries)
+        .set({
+          // Keep an exhausted claim owned until recordTerminal commits its outcome.
+          status: exhausted ? "delivering" : "pending",
+          ...(options.bounded ? { errorCount: nextErrorCount } : {}),
+          lastErrorCode: errorCode,
+          updatedAt: at,
+        })
+        .where(ownedClaim);
+    });
     return exhausted;
   }
 
@@ -1303,21 +1309,32 @@ export function questionResponseDeliveryService(
   async function sweepPending(limit = 50) {
     const sweepAt = now();
     const staleAt = new Date(sweepAt.getTime() - claimStaleMs);
-    await db
-      .update(issueQuestionResponseDeliveries)
-      .set({
-        status: "pending",
-        updatedAt: sweepAt,
-      })
-      .where(
-        and(
-          eq(issueQuestionResponseDeliveries.status, "delivering"),
-          or(
-            isNull(issueQuestionResponseDeliveries.lastAttemptAt),
-            lte(issueQuestionResponseDeliveries.lastAttemptAt, staleAt),
-          ),
+    await db.transaction(async (tx) => {
+      const staleClaims = await tx.select({
+        id: issueQuestionResponseDeliveries.id,
+        companyId: issueQuestionResponseDeliveries.companyId,
+        issueId: issueQuestionResponseDeliveries.issueId,
+      }).from(issueQuestionResponseDeliveries).where(and(
+        eq(issueQuestionResponseDeliveries.status, "delivering"),
+        or(
+          isNull(issueQuestionResponseDeliveries.lastAttemptAt),
+          lte(issueQuestionResponseDeliveries.lastAttemptAt, staleAt),
         ),
-      );
+      )).orderBy(asc(issueQuestionResponseDeliveries.id)).for("update");
+      if (staleClaims.length === 0) return;
+      const notified = new Set<string>();
+      for (const claim of staleClaims) {
+        const scope = `${claim.companyId}:${claim.issueId}`;
+        if (notified.has(scope)) continue;
+        await notifyChatRunMilestones(tx, claim);
+        notified.add(scope);
+      }
+      for (let offset = 0; offset < staleClaims.length; offset += 500) {
+        await tx.update(issueQuestionResponseDeliveries)
+          .set({ status: "pending", updatedAt: sweepAt })
+          .where(inArray(issueQuestionResponseDeliveries.id, staleClaims.slice(offset, offset + 500).map(claim => claim.id)));
+      }
+    });
     const ids = await db
       .select({ interactionId: issueQuestionResponseDeliveries.interactionId })
       .from(issueQuestionResponseDeliveries)