diff --git a/server/src/__tests__/native-cancellation-request.integration.test.ts b/server/src/__tests__/native-cancellation-request.integration.test.ts
index 15d4d554471..9ada636e8f2 100644
--- a/server/src/__tests__/native-cancellation-request.integration.test.ts
+++ b/server/src/__tests__/native-cancellation-request.integration.test.ts
@@ -1,21 +1,26 @@
 import { randomUUID } from "node:crypto";
 import { afterAll, beforeAll, describe, expect, it } from "vitest";
 import { eq, sql } from "drizzle-orm";
-import { agents, companies, createDb, heartbeatRuns } from "@paperclipai/db";
+import { agents, companies, createDb, heartbeatRuns, issues, nativeRunFinalizations } from "@paperclipai/db";
 import { startEmbeddedPostgresTestDatabase } from "./helpers/embedded-postgres.js";
 import { cancellationIntentId, claimCancellationRequest, startupCancellationFence } from "../services/native-runtime/native-cancellation-request.js";
 
 describe("atomic caller cancellation request ownership", () => {
   let database: Awaited<ReturnType<typeof startEmbeddedPostgresTestDatabase>>;
   let db: ReturnType<typeof createDb>;
-  beforeAll(async () => { database = await startEmbeddedPostgresTestDatabase("caller-stop-"); db = createDb(database.connectionString); }, 90_000);
+  let cancelNativeSession: typeof import("../services/native-runtime/native-session-executor.js").cancelNativeSession;
+  beforeAll(async () => {
+    ({ cancelNativeSession } = await import("../services/native-runtime/native-session-executor.js"));
+    database = await startEmbeddedPostgresTestDatabase("caller-stop-");
+    db = createDb(database.connectionString);
+  }, 90_000);
   afterAll(async () => { await database?.cleanup(); });
   async function fixture() {
     const companyId = randomUUID(), agentId = randomUUID(), runId = randomUUID();
     await db.insert(companies).values({ id: companyId, name: "Stop claims", issuePrefix: randomUUID().slice(0, 8) });
     await db.insert(agents).values({ id: agentId, companyId, name: "Stop target" });
     await db.insert(heartbeatRuns).values({ id: runId, companyId, agentId, invocationSource: "on_demand", status: "running", runtimeMode: "native" });
-    return { companyId, runId };
+    return { companyId, runId, agentId };
   }
   const defaultFence = (runId: string) => db.update(heartbeatRuns).set({ resultJson: sql`coalesce(${heartbeatRuns.resultJson}, '{}'::jsonb) || jsonb_build_object('startupCancellation', ${startupCancellationFence(new Date().toISOString())})` }).where(eq(heartbeatRuns.id, runId));
   it("allows exactly one of two concurrent identities and idempotent same-ID retries", async () => {
@@ -51,4 +56,49 @@ describe("atomic caller cancellation request ownership", () => {
     await db.update(heartbeatRuns).set({ resultJson: { ...run.resultJson, nativeCancellation: { intentId: cancellationIntentId(id) } } }).where(eq(heartbeatRuns.id, runId));
     await expect(claimCancellationRequest(db, runId, companyId, id, "board-user")).rejects.toMatchObject({ status: 409 });
   });
+  async function retryFixture(phase = "retryable_failure") {
+    const f = await fixture(), issueId = randomUUID();
+    await db.insert(issues).values({ id: issueId, companyId: f.companyId, title: "Native retry", status: "in_progress", assigneeAgentId: f.agentId });
+    await db.update(heartbeatRuns).set({ nativeIssueId: issueId, status: "failed" }).where(eq(heartbeatRuns.id, f.runId));
+    await db.insert(nativeRunFinalizations).values({ runId: f.runId, companyId: f.companyId, issueId, phase, nextAttemptAt: new Date(Date.now() + 30_000) });
+    return { ...f, issueId };
+  }
+  it("admits a failed retry and recovers the same caller after audited native cancellation disables it", async () => {
+    const f = await retryFixture(), id = randomUUID();
+    await claimCancellationRequest(db, f.runId, f.companyId, id, "board-user");
+    // No provider is attached: exercise the actual durable cancellation path.
+    const outcome = await cancelNativeSession(f.runId, "Stop", { db, scope: "run", cancellationRequestId: id });
+    expect(outcome.auditId).toBeTruthy();
+    const [coordinator] = await db.select().from(nativeRunFinalizations).where(eq(nativeRunFinalizations.runId, f.runId));
+    expect(coordinator).toMatchObject({ phase: "terminal_failure", failureCode: "native_retry_cancelled", nextAttemptAt: null });
+    const retried = await claimCancellationRequest(db, f.runId, f.companyId, id, "board-user");
+    expect(retried.resultJson?.nativeCancellation).toMatchObject({ intentId: cancellationIntentId(id), dispatchState: "acknowledged" });
+    await expect(claimCancellationRequest(db, f.runId, f.companyId, randomUUID(), "board-user")).rejects.toMatchObject({ status: 409 });
+    await expect(claimCancellationRequest(db, f.runId, f.companyId, id, "other-actor")).rejects.toMatchObject({ status: 409 });
+    await expect(cancelNativeSession(f.runId, "Stop", { db, scope: "run", cancellationRequestId: id })).resolves.toMatchObject({ auditId: outcome.auditId });
+  });
+  it.each(["observed", "terminal_failure", "committed"])("does not claim a failed run whose coordinator advanced to %s", async phase => {
+    const f = await retryFixture(phase);
+    await expect(claimCancellationRequest(db, f.runId, f.companyId, randomUUID(), "board-user")).rejects.toMatchObject({ status: 409 });
+    const [run] = await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, f.runId));
+    expect(run.resultJson?.startupCancellation).toBeUndefined();
+  });
+  it("rejects a coordinator-only concurrent claim, then observes its committed phase without installing a Stop fence", async () => {
+    const f = await retryFixture(), id = randomUUID();
+    let release!: () => void, locked!: () => void;
+    const acquired = new Promise<void>(resolve => { locked = resolve; });
+    const hold = new Promise<void>(resolve => { release = resolve; });
+    const advance = db.transaction(async tx => {
+      await tx.update(nativeRunFinalizations).set({ phase: "observed", nextAttemptAt: null }).where(eq(nativeRunFinalizations.runId, f.runId));
+      locked(); await hold;
+    });
+    try {
+      await acquired;
+      await expect(claimCancellationRequest(db, f.runId, f.companyId, id, "board-user")).rejects.toMatchObject({ status: 409, message: "Native retry cancellation is busy; retry the same request" });
+    } finally { release(); await advance; }
+    await expect(claimCancellationRequest(db, f.runId, f.companyId, id, "board-user")).rejects.toMatchObject({ status: 409 });
+    const [run] = await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, f.runId));
+    expect(run.resultJson?.startupCancellation).toBeUndefined();
+  });
+
 });
diff --git a/server/src/services/heartbeat.ts b/server/src/services/heartbeat.ts
index ba39981ae78..1e165d578ff 100644
--- a/server/src/services/heartbeat.ts
+++ b/server/src/services/heartbeat.ts
@@ -29146,20 +29146,23 @@ export function heartbeatService(
     if (options.cancellationRequestId) {
       run = await claimCancellationRequest(db, runId, run.companyId, options.cancellationRequestId, options.cancellationRequestedByUserId ?? null);
     }
+    // The caller claim checked retry eligibility under both durable row locks.
+    // Its own native intent may already have disabled the retry; re-reading only
+    // retryable_failure would strand that same-ID recovery.
     const pendingNativeRetry =
-      run.runtimeMode === "native" && run.status === "failed"
-        ? await db
-            .select({ runId: nativeRunFinalizations.runId })
-            .from(nativeRunFinalizations)
-            .where(
-              and(
-                eq(nativeRunFinalizations.runId, run.id),
-                eq(nativeRunFinalizations.companyId, run.companyId),
-                eq(nativeRunFinalizations.phase, "retryable_failure"),
-              ),
-            )
-            .then((rows) => rows.length > 0)
-        : false;
+      run.runtimeMode === "native" && run.status === "failed" && (
+        Boolean(options.cancellationRequestId) || await db
+          .select({ runId: nativeRunFinalizations.runId })
+          .from(nativeRunFinalizations)
+          .where(
+            and(
+              eq(nativeRunFinalizations.runId, run.id),
+              eq(nativeRunFinalizations.companyId, run.companyId),
+              eq(nativeRunFinalizations.phase, "retryable_failure"),
+            ),
+          )
+          .then((rows) => rows.length > 0)
+      );
     if (
       !pendingNativeRetry &&
       !CANCELLABLE_HEARTBEAT_RUN_STATUSES.includes(
diff --git a/server/src/services/native-runtime/native-cancellation-request.test.ts b/server/src/services/native-runtime/native-cancellation-request.test.ts
index 352f1f80ea3..0706ec5b57b 100644
--- a/server/src/services/native-runtime/native-cancellation-request.test.ts
+++ b/server/src/services/native-runtime/native-cancellation-request.test.ts
@@ -1,5 +1,6 @@
-import { describe, expect, it } from "vitest";
-import { assertCancellationRequest, cancellationIntentId, cancellationRequestId } from "./native-cancellation-request.js";
+import { describe, expect, it, vi } from "vitest";
+import { assertCancellationRequest, cancellationIntentId, cancellationRequestId, claimCancellationRequest } from "./native-cancellation-request.js";
+import { heartbeatRuns, type Db } from "@paperclipai/db";
 const id = "11111111-1111-4111-8111-111111111111";
 describe("caller-bound native cancellation", () => {
   it.each([null, "", " x", {}, [], 1, `${id} `, "not-a-uuid"])("rejects malformed request %j", value => {
@@ -21,3 +22,57 @@ describe("caller-bound native cancellation", () => {
     expect(() => assertCancellationRequest({ startupCancellation, nativeCancellation: { intentId: cancellationIntentId(id) } }, id)).not.toThrow();
   });
 });
+
+
+describe("failed native retry caller admission", () => {
+  const companyId = "company", runId = "run", issueId = "issue";
+  const claimed = { cancellationRequestId: id, requestedBy: { type: "board", userId: "board-user" } };
+  const native = { schema: "paperclip.native-cancellation.v1", intentId: cancellationIntentId(id),
+    companyId, runId, issueId, scope: "run", dispatchState: "pending", dispatched: false, intentAuditId: "intent-audit" };
+  function fixture(phase: string | null, resultJson: Record<string, unknown> = {}, status = "failed", failureCode: string | null = null) {
+    const run = { id: runId, companyId, nativeIssueId: issueId, runtimeMode: "native", status, resultJson };
+    const locks: unknown[][] = [];
+    const update = vi.fn((values: { resultJson: Record<string, unknown> }) => { run.resultJson = values.resultJson;
+      return { where: () => ({ returning: async () => [run] }) }; });
+    const tx = { select: () => ({ from: (table: unknown) => ({ where: () => ({
+      for: (...args: unknown[]) => { locks.push(args); return { limit: async () => table === heartbeatRuns ? [run]
+        : phase ? [{ phase, failureCode }] : [] }; },
+    }) }) }), update: () => ({ set: update }) };
+    const db = { transaction: async (fn: (value: typeof tx) => Promise<unknown>) => fn(tx) } as unknown as Db;
+    return { db, run, locks, update };
+  }
+  it("admits a pending retry under the coordinator lock and preserves the exact caller on retry", async () => {
+    const f = fixture("retryable_failure");
+    await claimCancellationRequest(f.db, runId, companyId, id, "board-user");
+    const first = structuredClone(f.run.resultJson);
+    await claimCancellationRequest(f.db, runId, companyId, id, "board-user");
+    expect(f.run.resultJson).toEqual(first);
+    expect(f.update).toHaveBeenCalledTimes(1);
+    expect(f.locks).toContainEqual(["update", { noWait: true }]);
+  });
+  it.each([null, "observed", "executing", "terminal_failure", "committed"])("rejects missing or advanced retry phase %s without writing", async phase => {
+    const f = fixture(phase);
+    await expect(claimCancellationRequest(f.db, runId, companyId, id, "board-user")).rejects.toMatchObject({ status: 409 });
+    expect(f.update).not.toHaveBeenCalled();
+  });
+  it.each(["pending", "acknowledged"])("recovers its own %s intent after native retry cancellation", async dispatchState => {
+    const f = fixture("terminal_failure", { startupCancellation: claimed,
+      nativeCancellation: { ...native, dispatchState, ...(dispatchState === "acknowledged" ? { acknowledgementAuditId: "ack-audit" } : {}) } }, "failed", "native_retry_cancelled");
+    await expect(claimCancellationRequest(f.db, runId, companyId, id, "board-user")).resolves.toMatchObject({ status: "failed" });
+    expect(f.update).not.toHaveBeenCalled();
+    await expect(claimCancellationRequest(f.db, runId, companyId, id, "another-actor")).rejects.toMatchObject({ status: 409 });
+  });
+  it.each([{}, { ...native, intentId: "foreign" }, { ...native, issueId: "foreign" },
+    { ...native, intentAuditId: null }, { ...native, dispatchState: "acknowledged" }])("rejects unproven or foreign cancellation recovery %j", nativeCancellation => {
+    const f = fixture("terminal_failure", { startupCancellation: claimed, nativeCancellation }, "failed", "native_retry_cancelled");
+    return expect(claimCancellationRequest(f.db, runId, companyId, id, "board-user")).rejects.toMatchObject({ status: 409 });
+  });
+  it.each(["succeeded", "cancelled", "timed_out"])("does not admit terminal %s merely because a retry row exists", status => {
+    const f = fixture("retryable_failure", {}, status);
+    return expect(claimCancellationRequest(f.db, runId, companyId, id, "board-user")).rejects.toMatchObject({ status: 409 });
+  });
+  it.each([{ code: "55P03" }, { cause: { code: "55P03" } }])("fails closed on coordinator contention without database details", async error => {
+    const db = { transaction: async () => { throw error; } } as unknown as Db;
+    await expect(claimCancellationRequest(db, runId, companyId, id, "board-user")).rejects.toMatchObject({ status: 409, message: "Native retry cancellation is busy; retry the same request" });
+  });
+});
diff --git a/server/src/services/native-runtime/native-cancellation-request.ts b/server/src/services/native-runtime/native-cancellation-request.ts
index ecdf8d4ec59..54d11f190c5 100644
--- a/server/src/services/native-runtime/native-cancellation-request.ts
+++ b/server/src/services/native-runtime/native-cancellation-request.ts
@@ -1,5 +1,5 @@
 import { and, eq, sql } from "drizzle-orm";
-import { heartbeatRuns, type Db } from "@paperclipai/db";
+import { heartbeatRuns, nativeRunFinalizations, type Db } from "@paperclipai/db";
 import { badRequest, conflict } from "../../errors.js";
 
 const UUID = /^[0-9a-f]{8}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{4}-[0-9a-f]{12}$/i;
@@ -34,10 +34,30 @@ export async function claimCancellationRequest(db: Db, runId: string, companyId:
     if (!run || run.runtimeMode !== "native") throw conflict("Correlated Stop requires a native run");
     assertCancellationRequest(run.resultJson, requestId, true);
     const result = record(run.resultJson);
+    let pendingRetry = false;
+    if (run.status === "failed" && run.nativeIssueId) {
+      // Eligibility and the caller fence must share a transaction. Coordinator
+      // writers need not lock the run. NOWAIT avoids a lock-order deadlock with
+      // execution's coordinator -> run claim; a busy claim can be retried.
+      const coordinator = await tx.select().from(nativeRunFinalizations)
+        .where(and(eq(nativeRunFinalizations.runId, runId), eq(nativeRunFinalizations.companyId, companyId),
+          eq(nativeRunFinalizations.issueId, run.nativeIssueId)))
+        .for("update", { noWait: true }).limit(1).then(rows => rows[0]);
+      const native = record(result.nativeCancellation);
+      const ownIntent = record(result.startupCancellation).cancellationRequestId === requestId
+        && native.schema === "paperclip.native-cancellation.v1" && native.intentId === cancellationIntentId(requestId)
+        && native.runId === runId && native.companyId === companyId && native.issueId === run.nativeIssueId
+        && native.scope === "run" && ["pending", "acknowledged"].includes(String(native.dispatchState))
+        && typeof native.dispatched === "boolean" && typeof native.intentAuditId === "string" && !!native.intentAuditId
+        && (native.dispatchState === "pending" || (typeof native.acknowledgementAuditId === "string"
+          && !!native.acknowledgementAuditId && native.acknowledgementAuditId !== native.intentAuditId));
+      pendingRetry = coordinator?.phase === "retryable_failure"
+        || (coordinator?.phase === "terminal_failure" && coordinator.failureCode === "native_retry_cancelled" && ownIntent);
+    }
     if (record(result.startupCancellation).cancellationRequestId === requestId) {
       const actor = record(record(result.startupCancellation).requestedBy);
       if (actor.type !== "board" || actor.userId !== userId) throw conflict("Cancellation request belongs to another actor");
-      if (!["queued", "running", "scheduled_retry"].includes(run.status)) {
+      if (!pendingRetry && !["queued", "running", "scheduled_retry"].includes(run.status)) {
         const native = record(result.nativeCancellation);
         if (run.status !== "cancelled" || native.schema !== "paperclip.native-cancellation.v1"
           || native.intentId !== cancellationIntentId(requestId) || native.runId !== runId || native.companyId !== companyId
@@ -48,12 +68,20 @@ export async function claimCancellationRequest(db: Db, runId: string, companyId:
       }
       return run;
     }
-    if (!["queued", "running", "scheduled_retry"].includes(run.status)) throw conflict("Correlated Stop run is already terminal");
+    if (!pendingRetry && !["queued", "running", "scheduled_retry"].includes(run.status)) throw conflict("Correlated Stop run is already terminal");
     const [claimed] = await tx.update(heartbeatRuns).set({ resultJson: { ...result,
       startupCancellation: { requestedAt: new Date().toISOString(), beforeNativeSelection: false, cancellationRequestId: requestId, requestedBy: { type: "board", userId } },
     } }).where(and(eq(heartbeatRuns.id, runId), eq(heartbeatRuns.companyId, companyId))).returning();
     if (!claimed) throw conflict("Correlated Stop run changed");
     return claimed;
+  }).catch((error: unknown) => {
+    // postgres-js can be wrapped by Drizzle; retain no raw database detail in
+    // the public conflict while allowing the exact request to retry later.
+    const value = record(error);
+    if (value.code === "55P03" || record(value.cause).code === "55P03") {
+      throw conflict("Native retry cancellation is busy; retry the same request");
+    }
+    throw error;
   });
 }