diff --git a/server/src/__tests__/attention-service.test.ts b/server/src/__tests__/attention-service.test.ts
index c84acf77f35..8982e83898d 100644
--- a/server/src/__tests__/attention-service.test.ts
+++ b/server/src/__tests__/attention-service.test.ts
@@ -41,6 +41,7 @@ import {
 import { errorHandler } from "../middleware/index.js";
 import { attentionRoutes } from "../routes/attention.js";
 import { attentionService } from "../services/attention.js";
+import { issueThreadInteractionService } from "../services/issue-thread-interactions.js";
 import { decisionHistoryService } from "../services/decision-history.js";
 import { listAttentionExhaustedRuns } from "../services/attention-exhausted-runs.js";
 import { agentService } from "../services/agents.js";
@@ -1540,6 +1541,89 @@ describeEmbeddedPostgres("attention service", () => {
     expect(interactionIds).not.toContain(olderConfirmationId);
   });
 
+  it.each([
+    ["approved from chat", "accept"],
+    ["expired", "expire"],
+  ] as const)("does not resurface an older confirmation once the newest one is %s", async (_label, outcome) => {
+    const { companyId, workerId } = await seedCompany(outcome === "accept" ? "ATR" : "ATX");
+    const issueId = await insertIssue({
+      companyId,
+      identifier: outcome === "accept" ? "ATR-1" : "ATX-1",
+      title: "Re-asked sign-off",
+      status: "in_review",
+      assigneeAgentId: workerId,
+    });
+    const olderConfirmationId = randomUUID();
+    const newerConfirmationId = randomUUID();
+    await db.insert(issueThreadInteractions).values([
+      {
+        id: olderConfirmationId,
+        companyId,
+        issueId,
+        kind: "request_confirmation",
+        status: "pending",
+        continuationPolicy: "none",
+        createdByAgentId: workerId,
+        title: "Approve the plan",
+        payload: { version: 1, prompt: "Approve the plan?" },
+        createdAt: new Date("2026-11-05T12:00:00.000Z"),
+        updatedAt: new Date("2026-11-05T12:00:00.000Z"),
+      },
+      {
+        id: newerConfirmationId,
+        companyId,
+        issueId,
+        kind: "request_confirmation",
+        status: "pending",
+        continuationPolicy: "none",
+        createdByAgentId: workerId,
+        title: "Approve the plan (again)",
+        payload: { version: 1, prompt: "Approve the plan?" },
+        createdAt: new Date("2026-11-05T12:05:00.000Z"),
+        updatedAt: new Date("2026-11-05T12:05:00.000Z"),
+      },
+    ]);
+
+    const pendingIds = async () => (await attentionService(db).list(companyId, { userId: "board-user" })).items
+      .filter((item) => item.sourceKind === "issue_thread_interaction")
+      .map((item) => item.subject.id);
+    expect(await pendingIds()).toEqual([newerConfirmationId]);
+
+    if (outcome === "accept") {
+      // The chat card resolves the same canonical record through the same service.
+      await issueThreadInteractionService(db).acceptInteraction(
+        { id: issueId, companyId, projectId: null, goalId: null, status: "in_review" },
+        newerConfirmationId,
+        {},
+        { userId: "board-user" },
+      );
+    } else {
+      await db.update(issueThreadInteractions).set({
+        status: "expired",
+        result: { version: 1, outcome: "stale_target" },
+        resolvedAt: new Date("2026-11-05T12:10:00.000Z"),
+        updatedAt: new Date("2026-11-05T12:10:00.000Z"),
+      }).where(eq(issueThreadInteractions.id, newerConfirmationId));
+    }
+
+    expect(await pendingIds()).toEqual([]);
+  });
+
+  it("keeps a pending tool-action approval visible after a newer tool action is settled", async () => {
+    const { companyId, workerId } = await seedCompany("ATT");
+    const issueId = await insertIssue({ companyId, identifier: "ATT-1", title: "Two tool calls", status: "in_progress", assigneeAgentId: workerId });
+    const olderId = randomUUID();
+    const base = { companyId, issueId, kind: "request_confirmation" as const, continuationPolicy: "none" as const, createdByAgentId: workerId, title: "Approve tool action" };
+    await db.insert(issueThreadInteractions).values([
+      { ...base, id: olderId, status: "pending", payload: { version: 1, prompt: "Run A?", toolAction: { actionRequestId: randomUUID() } },
+        createdAt: new Date("2026-11-05T12:00:00.000Z"), updatedAt: new Date("2026-11-05T12:00:00.000Z") },
+      { ...base, id: randomUUID(), status: "accepted", payload: { version: 1, prompt: "Run B?", toolAction: { actionRequestId: randomUUID() } },
+        createdAt: new Date("2026-11-05T12:05:00.000Z"), updatedAt: new Date("2026-11-05T12:06:00.000Z"), resolvedAt: new Date("2026-11-05T12:06:00.000Z") },
+    ]);
+    const feed = await attentionService(db).list(companyId, { userId: "board-user" });
+    expect(feed.items.filter((item) => item.sourceKind === "issue_thread_interaction").map((item) => item.subject.id)).toEqual([olderId]);
+  });
+
   it("retains every independently bound quality approval alongside the newest ordinary confirmation", async () => {
     const { companyId, workerId } = await seedCompany("ATQ");
     const issueId = await insertIssue({ companyId, identifier: "ATQ-1", title: "Review copy and visual", status: "in_review", assigneeAgentId: workerId });
diff --git a/server/src/services/attention-retention.ts b/server/src/services/attention-retention.ts
index ddb74d682e5..378302faca3 100644
--- a/server/src/services/attention-retention.ts
+++ b/server/src/services/attention-retention.ts
@@ -2,7 +2,7 @@ import { and, eq, getTableColumns, inArray, isNull, sql, type SQL } from "drizzl
 import { agents, decisionRetention, decisions, heartbeatRuns,
   issueApprovals, issueRecoveryActions, issueThreadInteractions, issues, approvals, type Db } from "@paperclipai/db";
 import { evaluateAgentInvokability } from "./agent-invokability.js";
-import { HUMAN_RECOVERY_OWNER_TYPES, ATTENTION_BUDGET_WARNING_PERCENT, ATTENTION_AGENT_ERROR_STATUS, collapsePendingConfirmationsToNewest, listFailedRunsWithNewerRun, readRunIssueId, requiresReviewAttention, terminalBlockerRequiresAttention } from "./attention-source-eligibility.js";
+import { HUMAN_RECOVERY_OWNER_TYPES, ATTENTION_BUDGET_WARNING_PERCENT, ATTENTION_AGENT_ERROR_STATUS, collapsePendingConfirmationsToNewest, listFailedRunsWithNewerRun, loadNewestSettledConfirmationAt, readRunIssueId, requiresReviewAttention, terminalBlockerRequiresAttention } from "./attention-source-eligibility.js";
 import { decisionRetentionService, DEFAULT_DECISION_ARCHIVE_DAYS } from "./decision-retention.js";
 import type { createDeliveryWorkCoordinator } from "./delivery-work-coordinator.js";
 import { DELIVERY_QUEUES } from "./delivery-work-notifications.js";
@@ -116,7 +116,8 @@ export function attentionRetentionService(db: Db) {
         eq(issueThreadInteractions.companyId, companyId), inArray(issueThreadInteractions.issueId, confirmationIssueIds),
         eq(issueThreadInteractions.status, "pending"), eq(issueThreadInteractions.kind, "request_confirmation"),
         isNull(issueThreadInteractions.addresseeUserId))) : [];
-      const newest = new Set(collapsePendingConfirmationsToNewest(siblings.filter(boardAddressed)).map(row => row.id));
+      const newest = new Set(collapsePendingConfirmationsToNewest(siblings.filter(boardAddressed),
+        await loadNewestSettledConfirmationAt(database, companyId, confirmationIssueIds)).map(row => row.id));
       for (const row of rows) result.set(row.id, visibleIds.has(row.issueId) && boardAddressed(row)
         && (row.kind !== "request_confirmation" || newest.has(row.id)));
     }
diff --git a/server/src/services/attention-source-eligibility.ts b/server/src/services/attention-source-eligibility.ts
index 971ca5f1ee5..4505a31bbd5 100644
--- a/server/src/services/attention-source-eligibility.ts
+++ b/server/src/services/attention-source-eligibility.ts
@@ -1,5 +1,5 @@
 import { and, eq, gt, inArray, sql, type SQL } from "drizzle-orm";
-import { heartbeatRuns, issueRecoveryActions, type Db } from "@paperclipai/db";
+import { heartbeatRuns, issueRecoveryActions, issueThreadInteractions, type Db } from "@paperclipai/db";
 
 export const HUMAN_RECOVERY_OWNER_TYPES = ["user", "board"] as const;
 const OPEN_RECOVERY_ATTENTION_STATUSES = ["active", "escalated"] as const;
@@ -11,14 +11,26 @@ export function recoveryActionAttentionCondition() {
 export const ATTENTION_BUDGET_WARNING_PERCENT = 85;
 export const ATTENTION_AGENT_ERROR_STATUS = "error";
 
+function payloadFlag(payload: unknown, key: string) {
+  return Boolean(payload && typeof payload === "object" && key in payload && (payload as Record<string, unknown>)[key]);
+}
+
+/**
+ * A pending confirmation is superseded once the same issue has a newer
+ * ordinary confirmation — pending, or already answered/expired. Without the
+ * settled case, answering the newest card (from chat or anywhere else)
+ * resurfaces the older ask it replaced. Quality approvals stay
+ * independent; tool-action approvals are gates for distinct calls, so a settled
+ * one never hides another.
+ */
 export function collapsePendingConfirmationsToNewest<T extends {
   id: string;
   issueId: string;
   kind: string;
   createdAt: Date;
   payload: unknown;
-}>(rows: T[]) {
-  const independent = (row: T) => Boolean(row.payload && typeof row.payload === "object" && "qualityReview" in row.payload && row.payload.qualityReview);
+}>(rows: T[], newestSettledConfirmationAt: ReadonlyMap<string, Date> = new Map()) {
+  const independent = (row: T) => payloadFlag(row.payload, "qualityReview");
   const newestByGroup = new Map<string, T>();
   for (const row of rows) {
     if (row.kind !== "request_confirmation" || independent(row)) continue;
@@ -33,11 +45,33 @@ export function collapsePendingConfirmationsToNewest<T extends {
     }
   }
 
-  return rows.filter((row) => (
-    row.kind !== "request_confirmation"
-    || independent(row)
-    || newestByGroup.get(`${row.issueId}:${row.kind}`)?.id === row.id
-  ));
+  return rows.filter((row) => {
+    if (row.kind !== "request_confirmation" || independent(row)) return true;
+    if (newestByGroup.get(`${row.issueId}:${row.kind}`)?.id !== row.id) return false;
+    const settledAt = payloadFlag(row.payload, "toolAction") ? undefined : newestSettledConfirmationAt.get(row.issueId);
+    return !settledAt || settledAt.getTime() <= row.createdAt.getTime();
+  });
+}
+
+// Cancelled/failed replacements do not settle the ask, so an older card returns.
+const SETTLED_CONFIRMATION_STATUSES = ["accepted", "rejected", "answered", "expired"] as const;
+
+/** Newest answered/expired ordinary confirmation per issue (see the collapse above). */
+export async function loadNewestSettledConfirmationAt(db: Db, companyId: string, issueIds: string[]) {
+  const ids = [...new Set(issueIds)];
+  if (ids.length === 0) return new Map<string, Date>();
+  const rows = await db.select({
+    issueId: issueThreadInteractions.issueId,
+    createdAt: sql<string>`max(${issueThreadInteractions.createdAt})::text`,
+  }).from(issueThreadInteractions).where(and(
+    eq(issueThreadInteractions.companyId, companyId),
+    inArray(issueThreadInteractions.issueId, ids),
+    eq(issueThreadInteractions.kind, "request_confirmation"),
+    inArray(issueThreadInteractions.status, [...SETTLED_CONFIRMATION_STATUSES]),
+    sql`jsonb_typeof(${issueThreadInteractions.payload}->'qualityReview') is distinct from 'object'`,
+    sql`jsonb_typeof(${issueThreadInteractions.payload}->'toolAction') is distinct from 'object'`,
+  )).groupBy(issueThreadInteractions.issueId);
+  return new Map(rows.map((row) => [row.issueId, new Date(row.createdAt)]));
 }
 
 export function readRunIssueId(contextSnapshot: Record<string, unknown> | null) {
diff --git a/server/src/services/attention.ts b/server/src/services/attention.ts
index bbbf505f480..1f24e5d5881 100644
--- a/server/src/services/attention.ts
+++ b/server/src/services/attention.ts
@@ -1,4 +1,4 @@
-import { recoveryActionAttentionCondition, ATTENTION_BUDGET_WARNING_PERCENT, ATTENTION_AGENT_ERROR_STATUS, collapsePendingConfirmationsToNewest, readRunIssueId, listFailedRunsWithNewerRun, requiresReviewAttention, terminalBlockerRequiresAttention } from "./attention-source-eligibility.js";
+import { recoveryActionAttentionCondition, ATTENTION_BUDGET_WARNING_PERCENT, ATTENTION_AGENT_ERROR_STATUS, collapsePendingConfirmationsToNewest, loadNewestSettledConfirmationAt, readRunIssueId, listFailedRunsWithNewerRun, requiresReviewAttention, terminalBlockerRequiresAttention } from "./attention-source-eligibility.js";
 import { approvalExecutionIssueCondition, firstApprovalIssueId } from "./approval-visibility.js";
 import { and, asc, desc, eq, inArray, isNull, notInArray, or, sql, type SQL } from "drizzle-orm";
 import type { Db } from "@paperclipai/db";
@@ -1223,7 +1223,9 @@ export function attentionService(db: Db, serviceOptions: AttentionServiceOptions
           !evaluateAgentInvokability(companyAgentMap.get(row.addresseeAgentId), companyAgentRows).invokable)
         && (row.addresseeUserId === null || row.addresseeUserId === options.userId)
       );
-      const visibleInteractionRows = collapsePendingConfirmationsToNewest(boardInteractionRows);
+      const visibleInteractionRows = collapsePendingConfirmationsToNewest(boardInteractionRows, await loadNewestSettledConfirmationAt(
+        db, companyId, boardInteractionRows.filter((row) => row.kind === "request_confirmation").map((row) => row.issueId),
+      ));
       const [interactionIssueMap, interactionImageMap, interactionPlanDocumentMap] = await Promise.all([
         // A pending human request remains actionable in a persistent chat even
         // though its idle container is intentionally absent from work queues.