diff --git a/server/src/__tests__/issues-service.test.ts b/server/src/__tests__/issues-service.test.ts
index daa556d4231..ed2ec590efd 100644
--- a/server/src/__tests__/issues-service.test.ts
+++ b/server/src/__tests__/issues-service.test.ts
@@ -886,6 +886,17 @@ describeEmbeddedPostgres("issueService.list participantAgentId", () => {
         requestingAgentId: agentId, requestingAgentName: "ConnectionRequester", phase: "authorizing",
       },
     }).returning();
+    // A second pending request on the same issue asks for an AI account. The
+    // expiry must tell the two apart: only the AI one blocks the run.
+    const [aiInteraction] = await db.insert(issueThreadInteractions).values({
+      companyId, issueId: issue.id, kind: "connection_intent", status: "pending",
+      createdByAgentId: agentId, addresseeUserId: "local-board",
+      payload: {
+        version: 1, purpose: "ai", serviceSlug: "connection:claude_local",
+        serviceName: "Claude", requestingAgentId: agentId,
+        requestingAgentName: "ConnectionRequester", phase: "authorizing",
+      },
+    }).returning();
     const oauthState = randomUUID();
     await db.insert(toolOauthStates).values({
       state: oauthState, companyId, connectionId: connection!.id, issueId: issue.id,
@@ -901,9 +912,22 @@ describeEmbeddedPostgres("issueService.list participantAgentId", () => {
     await expect(db.select().from(issueThreadInteractions).where(eq(issueThreadInteractions.id, interaction!.id)))
       .resolves.toEqual([expect.objectContaining({
         status: "expired",
-        result: { version: 1, outcome: "expired", reason: "The task assignment changed" },
+        result: {
+          version: 1,
+          outcome: "expired",
+          reason: "The task was reassigned before the connection request was answered, so the Notion connection is still not connected. Reconnect it or choose an available connection.",
+        },
         resolvedAt: expect.any(Date),
       })]);
+    await expect(db.select().from(issueThreadInteractions).where(eq(issueThreadInteractions.id, aiInteraction!.id)))
+      .resolves.toEqual([expect.objectContaining({
+        status: "expired",
+        result: {
+          version: 1,
+          outcome: "expired",
+          reason: "The task was reassigned before the connection request was answered, so the AI account is still not connected. Reconnect it or choose an available connection.",
+        },
+      })]);
     await expect(db.select().from(toolOauthStates).where(eq(toolOauthStates.state, oauthState))).resolves.toEqual([]);
   });
 
diff --git a/server/src/services/issue-thread-interactions.ts b/server/src/services/issue-thread-interactions.ts
index 96049788e73..015ba84cf45 100644
--- a/server/src/services/issue-thread-interactions.ts
+++ b/server/src/services/issue-thread-interactions.ts
@@ -4746,12 +4746,46 @@ export function issueThreadInteractionService(
     },
 
     expireConnectionIntentsForOwnershipChange: async (issue: { id: string; companyId: string }) => {
-      const expired = await db.update(issueThreadInteractions).set({
-        status: "expired", result: { version: 1, outcome: "expired", reason: "The task assignment changed" },
-        resolvedAt: now(), updatedAt: now(),
-      }).where(and(eq(issueThreadInteractions.companyId, issue.companyId), eq(issueThreadInteractions.issueId, issue.id),
-        eq(issueThreadInteractions.kind, "connection_intent"), eq(issueThreadInteractions.status, "pending"))).returning();
-      if (expired.length) await db.delete(toolOauthStates).where(inArray(toolOauthStates.interactionId, expired.map((row) => row.id)));
+      // A pending connection_intent asks for either an AI account or a tool
+      // account, and the two leave different things broken. One bulk write gave
+      // every row the AI wording, so an expired Notion request told the reader
+      // the AI account was missing. Read the pending rows first and name the
+      // subject each row actually asked for.
+      const pending = await db
+        .select({ id: issueThreadInteractions.id, payload: issueThreadInteractions.payload })
+        .from(issueThreadInteractions)
+        .where(and(
+          eq(issueThreadInteractions.companyId, issue.companyId),
+          eq(issueThreadInteractions.issueId, issue.id),
+          eq(issueThreadInteractions.kind, "connection_intent"),
+          eq(issueThreadInteractions.status, "pending"),
+        ));
+      const expired: typeof issueThreadInteractions.$inferSelect[] = [];
+      for (const row of pending) {
+        const payload = row.payload as { purpose?: string; serviceName?: string } | null;
+        const subject = payload?.purpose === "ai"
+          ? "the AI account"
+          : `the ${payload?.serviceName?.trim() || "requested"} connection`;
+        const [updated] = await db
+          .update(issueThreadInteractions)
+          .set({
+            status: "expired",
+            result: {
+              version: 1,
+              outcome: "expired",
+              reason: `The task was reassigned before the connection request was answered, so ${subject} is still not connected. Reconnect it or choose an available connection.`,
+            },
+            resolvedAt: now(),
+            updatedAt: now(),
+          })
+          .where(and(
+            eq(issueThreadInteractions.id, row.id),
+            eq(issueThreadInteractions.status, "pending"),
+          ))
+          .returning();
+        if (updated) expired.push(updated);
+      }
+      if (expired.length) await db.delete(toolOauthStates).where(inArray(toolOauthStates.interactionId, expired.map((item) => item.id)));
       return expired;
     },
     expirePendingInteractionsForTerminalIssue: async (
diff --git a/ui/src/features/connections/ConnectionIntentInteractionBody.test.tsx b/ui/src/features/connections/ConnectionIntentInteractionBody.test.tsx
index 406eb0fcf63..f9ac280ec45 100644
--- a/ui/src/features/connections/ConnectionIntentInteractionBody.test.tsx
+++ b/ui/src/features/connections/ConnectionIntentInteractionBody.test.tsx
@@ -259,6 +259,18 @@ describe("ConnectionIntentInteractionBody states and audience", () => {
     expect(document.body.textContent).toContain(expected);
   });
 
+  it("shows the stored reason on an expired request", () => {
+    // The server writes what actually expired the request and what to do next.
+    // A generic "no longer active" line left the reader with no next step.
+    const reason = "The task was reassigned before the connection request was answered, so the Notion connection is still not connected. Reconnect it or choose an available connection.";
+    renderBody({
+      ...terminal("expired", "expired"),
+      result: { version: 1, outcome: "expired", reason },
+    } as ConnectionIntentInteraction);
+    expect(document.body.textContent).toContain(reason);
+    expect(document.body.textContent).not.toContain("This request is no longer active.");
+  });
+
   it("shows non-addressees only the waiting state and never loads setup", () => {
     renderBody(pendingConnectionIntentInteraction, "other-user");
     expect(document.body.textContent).toContain("Waiting for Carol");
diff --git a/ui/src/features/connections/ConnectionIntentInteractionBody.tsx b/ui/src/features/connections/ConnectionIntentInteractionBody.tsx
index 48a56139bed..a87af21f786 100644
--- a/ui/src/features/connections/ConnectionIntentInteractionBody.tsx
+++ b/ui/src/features/connections/ConnectionIntentInteractionBody.tsx
@@ -268,7 +268,10 @@ export function ConnectionIntentInteractionBody({
               body:
                 resultOutcome === "superseded"
                   ? "This request was replaced. Use the latest connection card instead."
-                  : "This request is no longer active.",
+                  : // The server stores the reason an expiry happened and what to
+                    // do next; without it the card only says the request is gone.
+                    interaction.result?.reason?.trim()
+                    || "This request is no longer active.",
             }
           : null;
   const StatusIcon = status?.icon;