diff --git a/server/src/__tests__/interrupted-preparation-hold-settle.test.ts b/server/src/__tests__/interrupted-preparation-hold-settle.test.ts
new file mode 100644
index 00000000000..45062ed7114
--- /dev/null
+++ b/server/src/__tests__/interrupted-preparation-hold-settle.test.ts
@@ -0,0 +1,133 @@
+import { randomUUID } from "node:crypto";
+import { eq } from "drizzle-orm";
+import { afterAll, afterEach, beforeAll, describe, expect, it } from "vitest";
+import {
+  activityLog,
+  agents,
+  companies,
+  createDb,
+  environmentLeases,
+  environments,
+  heartbeatRunEvents,
+  heartbeatRuns,
+  issueRecoveryActions,
+  issues,
+} from "@paperclipai/db";
+import { getEmbeddedPostgresTestSupport, startEmbeddedPostgresTestDatabase } from "./helpers/embedded-postgres.js";
+import { legacyControllerBootId } from "../services/legacy-controller-lease.js";
+import { heartbeatService } from "../services/heartbeat.js";
+import { settleHeldInterruptedPreparations } from "../services/legacy-execution-recovery.js";
+
+const support = await getEmbeddedPostgresTestSupport();
+const suite = support.supported ? describe : describe.skip;
+
+/**
+ * The K2-during-preparation shape from Daytona warm wave w-20261108T142906-s9501
+ * (t05, run c99b3a2e): a scheduled retry was 2 s into preparation when a
+ * graceful shutdown interrupted it. The draining process recorded a
+ * preserve-without-replay hold, because at that moment its own controller was
+ * still live and the sandbox lease was still being cleaned up. The lease was
+ * released with a confirmed stop moments later, and the next process booted,
+ * but nothing re-judged the hold, so the task waited for a manual Retry.
+ */
+suite("held interrupted preparations after a restart", () => {
+  let db!: ReturnType<typeof createDb>;
+  let temporary: Awaited<ReturnType<typeof startEmbeddedPostgresTestDatabase>> | null = null;
+  let companyId = "", agentId = "", environmentId = "";
+
+  beforeAll(async () => {
+    temporary = await startEmbeddedPostgresTestDatabase("paperclip-interrupted-preparation-");
+    db = createDb(temporary.connectionString);
+    companyId = randomUUID(); agentId = randomUUID(); environmentId = randomUUID();
+    await db.insert(companies).values({ id: companyId, name: "Paperclip", issuePrefix: "IPH",
+      requireBoardApprovalForNewAgents: false });
+    await db.insert(agents).values({ id: agentId, companyId, name: "Coder", role: "engineer", status: "idle",
+      adapterType: "paperclip_runner", adapterConfig: {}, runtimeConfig: {}, permissions: {} });
+    await db.insert(environments).values({ id: environmentId, name: "Sandbox", driver: "sandbox", status: "active",
+      config: { provider: "fake" } });
+  }, 30_000);
+
+  afterEach(async () => {
+    await db.delete(activityLog);
+    await db.delete(issueRecoveryActions);
+    await db.delete(environmentLeases);
+    await db.delete(heartbeatRunEvents);
+    await db.delete(heartbeatRuns);
+    await db.delete(issues);
+  });
+
+  afterAll(async () => { await temporary?.cleanup(); });
+
+  async function interruptedPreparation(options: { controllerBootId?: string; leaseReleased?: boolean } = {}) {
+    const issueId = randomUUID(), runId = randomUUID(), leaseId = randomUUID(), providerLeaseId = `sandbox-${leaseId}`;
+    const finishedAt = new Date(Date.now() - 10_000);
+    await db.insert(issues).values({ id: issueId, companyId, title: "Warm follow-up", status: "in_progress",
+      assigneeAgentId: agentId });
+    await db.insert(heartbeatRuns).values({ id: runId, companyId, agentId, invocationSource: "automation",
+      status: "interrupted", errorCode: "server_shutdown_interrupted", runtimeMode: "legacy", executionStage: "preparing",
+      startedAt: new Date(finishedAt.getTime() - 2_000), finishedAt, nextEventSeq: 1,
+      controllerBootId: options.controllerBootId ?? randomUUID(),
+      scheduledRetryAttempt: 1, scheduledRetryReason: "transient_failure",
+      contextSnapshot: { issueId },
+      runnerProfileJson: { adapterDispatch: { adapterType: "paperclip_runner" } },
+      resultJson: { stopReason: "interrupted", cancellation: { reason: "Server shutdown interrupted execution",
+        source: "shutdown", expected: true, initiator: { type: "system" }, recordedAt: finishedAt.toISOString() } } });
+    const released = options.leaseReleased !== false;
+    await db.insert(environmentLeases).values({ id: leaseId, companyId, environmentId, issueId, heartbeatRunId: runId,
+      status: released ? "released" : "pending_cleanup", cleanupStatus: released ? "success" : "failed",
+      leasePolicy: "reuse_by_environment", provider: "fake", providerLeaseId,
+      releasedAt: released ? new Date(finishedAt.getTime() + 2_000) : null,
+      metadata: released ? { remoteExecutionTermination: { schema: "paperclip.remote-termination.v1", companyId, runId,
+        leaseId, provider: "fake", providerLeaseId, state: "stopped", confirmedAt: finishedAt.toISOString() } } : {} });
+    const [hold] = await db.insert(issueRecoveryActions).values({ companyId, sourceIssueId: issueId,
+      kind: "execution_reconciliation", cause: "legacy_execution_requires_reconciliation",
+      fingerprint: `legacy-execution:${runId}`, status: "resolved", outcome: "blocked", ownerType: "board",
+      nextAction: "Inspect the stopped provider and recorded actions.", resolvedAt: finishedAt,
+      evidence: { runId, automaticRecovery: { policy: "preserve_without_replay_v1", runId, replay: "blocked",
+        actionOutcome: "unknown", recordedAt: finishedAt.toISOString() } } }).returning();
+    return { issueId, runId, holdId: hold!.id };
+  }
+
+  const hold = async (id: string) => (await db.select().from(issueRecoveryActions).where(eq(issueRecoveryActions.id, id)))[0]!;
+  const runRow = async (id: string) => (await db.select().from(heartbeatRuns).where(eq(heartbeatRuns.id, id)))[0]!;
+
+  it("replays a preparation interrupted by a restart once durable proof shows no provider work started", async () => {
+    const f = await interruptedPreparation();
+    await settleHeldInterruptedPreparations(db);
+    const settled = await hold(f.holdId);
+    expect(settled).toMatchObject({ status: "resolved", outcome: "false_positive" });
+    expect(settled.evidence).toMatchObject({ automaticRecovery: { replay: "allowed" },
+      bootstrapPreparationContinuation: "pending", bootstrapPreparationSettledAt: expect.any(String) });
+    expect((await runRow(f.runId)).resultJson).toMatchObject({
+      executionRecovery: { kind: "bootstrap", providerWorkStarted: false } });
+  });
+
+  it("orphan recovery after a restart settles the hold without a user Retry", async () => {
+    const f = await interruptedPreparation();
+    await heartbeatService(db).reapOrphanedRuns();
+    expect(await hold(f.holdId)).toMatchObject({ status: "resolved", outcome: "false_positive" });
+  });
+
+  it.each([
+    ["provider work may have started", async (f: { runId: string }) => {
+      await db.insert(heartbeatRunEvents).values({ companyId, runId: f.runId, agentId, seq: 1, eventType: "turn.started",
+        stream: "system", level: "info", message: "turn started" });
+    }],
+    ["the controller that owned it is still this process", async (f: { runId: string }) => {
+      await db.update(heartbeatRuns).set({ controllerBootId: legacyControllerBootId }).where(eq(heartbeatRuns.id, f.runId));
+    }],
+  ] as const)("keeps the hold when %s", async (_label, arrange) => {
+    const f = await interruptedPreparation();
+    await arrange(f);
+    const before = await hold(f.holdId);
+    await settleHeldInterruptedPreparations(db);
+    expect(await hold(f.holdId)).toEqual(before);
+  });
+
+  it("keeps the hold while the sandbox lease is still being cleaned up", async () => {
+    const f = await interruptedPreparation({ leaseReleased: false });
+    const before = await hold(f.holdId);
+    await settleHeldInterruptedPreparations(db);
+    expect(await hold(f.holdId)).toEqual(before);
+  });
+});
diff --git a/server/src/services/heartbeat/recovery.ts b/server/src/services/heartbeat/recovery.ts
index 71a86bd8c7a..98cb262a72e 100644
--- a/server/src/services/heartbeat/recovery.ts
+++ b/server/src/services/heartbeat/recovery.ts
@@ -47,7 +47,7 @@ import {
 import { remoteTerminationReceipt } from "../remote-execution-termination.js";
 import { readEnvironmentStopFailure, type PluginEnvironmentStopFailure } from "@paperclipai/plugin-sdk";
 import { runUsedConversationAdapter } from "../conversation-continuation.js";
-import { legacyExecutionNeedsReconciliationWithEvidence, terminalizeLegacyExecution } from "../legacy-execution-recovery.js";
+import { legacyExecutionNeedsReconciliationWithEvidence, settleHeldInterruptedPreparations, terminalizeLegacyExecution } from "../legacy-execution-recovery.js";
 import { reconcileRetainedWorkspaces } from "../workspace-recovery.js";
 import { randomUUID } from "node:crypto";
 import os from "node:os";
@@ -2864,6 +2864,11 @@ export function createHeartbeatRecovery(db: Db, dependencies: HeartbeatRecoveryD
     });
     if (!opts?.skipRetainedNativeSessionCleanup) scheduleRetainedNativeSessionCleanup();
     await reconcileRetainedWorkspaces(db, environmentRuntime, resumeRemoteStopComments);
+    // A shutdown can hold a run it interrupted in preparation before the proof
+    // that no provider work started exists; once it does, replay that run.
+    await settleHeldInterruptedPreparations(db).catch(error => {
+      logger.warn({ err: error }, "failed to re-judge held interrupted preparations");
+    });
     if (!opts?.skipNativeStatusWakeIntents) await dispatchPendingNativeStatusWakeups().catch((error) => {
       logger.warn(
         { err: error },
diff --git a/server/src/services/legacy-execution-recovery.ts b/server/src/services/legacy-execution-recovery.ts
index 978528a0246..15a6ed25d66 100644
--- a/server/src/services/legacy-execution-recovery.ts
+++ b/server/src/services/legacy-execution-recovery.ts
@@ -392,6 +392,36 @@ export async function settleInterruptedNativeBootstrap(
   });
 }
 
+/**
+ * Re-judges preparation holds once their proof can exist. A graceful shutdown
+ * terminalizes a run still in preparation inside the draining process: its own
+ * controller is live and its sandbox lease may still be cleaning up, so the
+ * no-provider-work proof (`isInterruptedNativePreparation`) cannot hold yet and
+ * the run is held for reconciliation. Once the owning process is gone and the
+ * leases are released with confirmed stops, that proof decides: a run with no
+ * provider execution is settled and its preparation is replayed in its own
+ * uncharged lane. Anything with possible provider work, or without proof, stays
+ * held. Recovery runs this after every restart.
+ */
+export async function settleHeldInterruptedPreparations(db: Db, options: { limit?: number } = {}): Promise<number> {
+  const candidates = await db.select().from(heartbeatRuns).where(and(
+    inArray(heartbeatRuns.status, ["interrupted", "failed"]), eq(heartbeatRuns.runtimeMode, "legacy"),
+    isNull(heartbeatRuns.runtimeModeResolvedAt), eq(heartbeatRuns.executionStage, "preparing"),
+    sql`exists (select 1 from issue_recovery_actions hold where hold.company_id = ${heartbeatRuns.companyId}
+      and hold.cause = ${LEGACY_RECOVERY_CAUSE} and hold.fingerprint = 'legacy-execution:' || ${heartbeatRuns.id}::text
+      and hold.evidence->>'runId' = ${heartbeatRuns.id}::text and not (hold.evidence ? 'executionReconciliation')
+      and (hold.status in ('active', 'escalated') or (hold.status = 'resolved' and hold.outcome = 'blocked'
+        and hold.evidence->'automaticRecovery'->>'policy' = 'preserve_without_replay_v1'
+        and hold.evidence->'automaticRecovery'->>'replay' = 'blocked')))`,
+  )).orderBy(heartbeatRuns.finishedAt).limit(options.limit ?? 50);
+  let settled = 0;
+  for (const run of candidates) {
+    if (!await isInterruptedNativePreparation(db, run)) continue;
+    if (await settleInterruptedNativeBootstrap(db, { run, providerDispatchStarted: false })) settled += 1;
+  }
+  return settled;
+}
+
 /** The source stays discoverable until normal admission records a successor.
  * Known admission gates wait for eligibility events; unresolved writes retain
  * the pending delivery deadline. Concurrent successful delivery never regresses. */