diff --git a/server/src/__tests__/agent-conversations.test.ts b/server/src/__tests__/agent-conversations.test.ts
index 049e2f8062..edc861e41b 100644
--- a/server/src/__tests__/agent-conversations.test.ts
+++ b/server/src/__tests__/agent-conversations.test.ts
@@ -34,6 +34,8 @@ import {
 import { issueService } from "../services/issues.js";
 import { documentService } from "../services/documents.js";
 import { getTaskPlanContext } from "../services/task-plan-context.js";
+import { terminalizeLegacyExecution, LEGACY_RECOVERY_CAUSE } from "../services/legacy-execution-recovery.js";
+import { settleUnrecoverableExecutions } from "../services/execution-recovery-resolution.js";
 import { renderPaperclipWakePrompt } from "@paperclipai/adapter-utils/server-utils";
 import { instanceSettingsService } from "../services/instance-settings.js";
 import {
@@ -777,6 +779,49 @@ const support = await getEmbeddedPostgresTestSupport();
       expect((await issueService(db).getDependencyReadiness(chat.id)).blockerIssueIds).toEqual([blocker.id]);
     });
 
+    it.each([
+      { name: "reset idle chat", generation: 1, sourceGeneration: 0, waiting: true, ordinary: false, superseded: true },
+      { name: "reset active chat", generation: 1, sourceGeneration: 0, waiting: false, ordinary: false, superseded: true },
+      { name: "newer reply in the same session", generation: 1, sourceGeneration: 1, waiting: true, ordinary: false, superseded: true },
+      { name: "current unanswered chat turn", generation: 1, sourceGeneration: 1, waiting: false, ordinary: false, superseded: false },
+      { name: "unprepared failure without a session generation", generation: 1, sourceGeneration: undefined, waiting: true, ordinary: false, superseded: false },
+      { name: "ordinary review task", generation: 0, sourceGeneration: 0, waiting: true, ordinary: true, superseded: false },
+    ])("guards delayed cancelled-run recovery for $name", async (scenario) => {
+      const task = scenario.ordinary
+        ? await issueService(db).create(companyId, { title: "Ordinary review", status: "in_review", assigneeAgentId: agentId })
+        : await create();
+      const status = scenario.waiting ? "in_review" : "in_progress";
+      await db.update(issues).set({
+        status,
+        ...(scenario.ordinary ? {} : {
+          conversationSessionGeneration: scenario.generation,
+          conversationState: scenario.waiting ? "waiting" : "active",
+        }),
+      }).where(eq(issues.id, task.id));
+      const run = await runFor(task.id, randomUUID(), {
+        conversationSessionGeneration: scenario.sourceGeneration,
+      });
+      await terminalizeLegacyExecution({ db, run, status: "cancelled", patch: { finishedAt: new Date() } });
+      let actions = await db.select().from(issueRecoveryActions).where(eq(issueRecoveryActions.sourceIssueId, task.id));
+      expect(actions).toHaveLength(scenario.superseded ? 0 : 1);
+      // Also exercise an action queued before /new or the newer reply settled.
+      if (!actions.length) {
+        actions = await db.insert(issueRecoveryActions).values({
+          companyId, sourceIssueId: task.id, kind: "active_run_watchdog",
+          ownerType: "board", returnOwnerAgentId: agentId,
+          cause: LEGACY_RECOVERY_CAUSE, fingerprint: `legacy-execution:${run.id}`,
+          evidence: { runId: run.id }, nextAction: "Reconcile stopped work",
+        }).returning();
+      }
+      await settleUnrecoverableExecutions(db);
+      const [after] = await db.select().from(issues).where(eq(issues.id, task.id));
+      const [action] = await db.select().from(issueRecoveryActions).where(eq(issueRecoveryActions.id, actions[0]!.id));
+      expect(after.status).toBe(scenario.superseded ? status : "blocked");
+      expect(action).toMatchObject({ status: "resolved", outcome: scenario.superseded ? "cancelled" : "blocked" });
+      expect((await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, run.id)))[0].status).toBe("cancelled");
+      if (!scenario.ordinary) expect(after.conversationSessionGeneration).toBe(scenario.generation);
+    });
+
     it("only parks answered turns and preserves idle across recovery classification", async () => {
       const issue = await create();
       const message = await issueService(db).addComment(
diff --git a/server/src/services/agent-conversations.ts b/server/src/services/agent-conversations.ts
index 0ebdb1b6f4..e0efab65ef 100644
--- a/server/src/services/agent-conversations.ts
+++ b/server/src/services/agent-conversations.ts
@@ -38,6 +38,26 @@ export function isWaitingConversation(
     issue.status === "in_review"
   );
 }
+
+/** Recovery for an older turn must not replace a reset or an answered chat. */
+export function isSupersededConversationRun(
+  issue: ConversationIdentity & {
+    conversationSessionGeneration?: number;
+    executionRunId?: string | null;
+  },
+  run: { id: string; contextSnapshot: Record<string, unknown> | null },
+): boolean {
+  if (!isConversation(issue)) return false;
+  const generation = run.contextSnapshot?.conversationSessionGeneration;
+  return (
+    (typeof generation === "number" &&
+      typeof issue.conversationSessionGeneration === "number" &&
+      generation !== issue.conversationSessionGeneration) ||
+    (typeof generation === "number" &&
+      isWaitingConversation(issue) &&
+      issue.executionRunId !== run.id)
+  );
+}
 /** Execution tasks may link to a conversation, but never drive its turns.
  * Apply before enqueue, including while a reply is still running: waiting until
  * finalization is too late to prevent a deferred dependency follow-up.
diff --git a/server/src/services/execution-recovery-resolution.ts b/server/src/services/execution-recovery-resolution.ts
index a605c7b43b..6d802b005a 100644
--- a/server/src/services/execution-recovery-resolution.ts
+++ b/server/src/services/execution-recovery-resolution.ts
@@ -18,6 +18,7 @@ import {
   type ExecutionReconciliation,
 } from "@paperclipai/shared";
 import { parseIssueExecutionState } from "./issue-execution-policy.js";
+import { isSupersededConversationRun } from "./agent-conversations.js";
 
 /** An operator records observed outcomes; this is not permission to blindly retry. */
 export async function validateExecutionReconciliation(input: {
@@ -397,6 +398,7 @@ export async function settleUnrecoverableExecutions(
         )
           return;
         const current =
+          !isSupersededConversationRun(task, run) &&
           action.returnOwnerAgentId !== null &&
           task.assigneeAgentId === action.returnOwnerAgentId &&
           !["done", "cancelled"].includes(task.status) &&
diff --git a/server/src/services/legacy-execution-recovery.ts b/server/src/services/legacy-execution-recovery.ts
index cc1a2c0b94..6a7d5c06bf 100644
--- a/server/src/services/legacy-execution-recovery.ts
+++ b/server/src/services/legacy-execution-recovery.ts
@@ -5,6 +5,7 @@ import { heartbeatRuns, issueRecoveryActions, issues, type Db } from "@paperclip
 import { issueRecoveryActionService } from "./issue-recovery-actions.js";
 import { parseIssueExecutionState } from "./issue-execution-policy.js";
 import { executionFailureRetryCount } from "./execution-recovery-attempt.js";
+import { isSupersededConversationRun } from "./agent-conversations.js";
 
 type Run = typeof heartbeatRuns.$inferSelect;
 export const LEGACY_RECOVERY_CAUSE = "legacy_execution_requires_reconciliation";
@@ -95,6 +96,7 @@ export async function terminalizeLegacyExecution(input: {
       review.currentParticipant?.type === "agent" && review.currentParticipant.agentId === run.agentId;
     if (
       task &&
+      !isSupersededConversationRun(task, updated) &&
       (task.assigneeAgentId === run.agentId || isCurrentReviewer) &&
       !["done", "cancelled"].includes(task.status)
     ) {