diff --git a/doc/DEVELOPING.md b/doc/DEVELOPING.md
index aa0ecf30a0a..9d23e4d847d 100644
--- a/doc/DEVELOPING.md
+++ b/doc/DEVELOPING.md
@@ -3422,6 +3422,13 @@ and `packages/adapter-utils/src/sandbox-callback-bridge.test.ts` for these contr
 
 ### Native runner restart recovery
 
+An explicit Retry can continue a recovered setup failure that began as a
+scheduled retry. Its settlement proof accepts the host-authored promotion event
+only when its deadline, reason and attempt match the run and its saved retry
+context. The exact failure and durable measurement must still follow. Provider
+dispatch evidence, an active controller, unsafe files or changed user authority
+keep the Retry held. This adds no automatic replay or recovery loop.
+
 For remote controller disk-loss work, use the existing control-plane snapshot
 transaction and `native-controller-recovery.ts`; do not add a second snapshot
 writer. The private versioned metadata is limited to 4 KiB. Its importer handles
diff --git a/server/src/services/failed-preparation-settlement.ts b/server/src/services/failed-preparation-settlement.ts
index a9d6551a2fc..3fb3844b73a 100644
--- a/server/src/services/failed-preparation-settlement.ts
+++ b/server/src/services/failed-preparation-settlement.ts
@@ -1,4 +1,4 @@
-import { and, asc, eq } from "drizzle-orm";
+import { and, asc, eq, sql } from "drizzle-orm";
 import { heartbeatRunEvents, heartbeatRuns, type Db } from "@paperclipai/db";
 import { isUuidLike } from "@paperclipai/shared";
 
@@ -10,19 +10,25 @@ export async function readFailedPreparationSettlement(db: Db, source: Source, al
   if (typeof source.error !== "string" || !source.error.length) return null;
   const events = await db.select().from(heartbeatRunEvents).where(and(
     eq(heartbeatRunEvents.companyId, source.companyId), eq(heartbeatRunEvents.runId, source.id),
-  )).orderBy(asc(heartbeatRunEvents.seq)).limit(allowRunStarted ? 5 : 4);
+  )).orderBy(asc(heartbeatRunEvents.seq)).limit(allowRunStarted ? 6 : 5);
   const hostEvent = (event: typeof heartbeatRunEvents.$inferSelect) => event.agentId === source.agentId
     && event.stream === "system" && event.sourceInstanceId === null && event.sourceEventId === null
     && event.sourceSeq === null && event.sourcePayloadSha256 === null && event.protocolSchemaVersion === null;
   let offset = 0;
+  const promotion = events[0];
+  if (promotion?.message === "Scheduled retry became due and was promoted to the queued run pool") {
+    if (!hostEvent(promotion) || promotion.seq !== 1 || promotion.eventType !== "lifecycle"
+      || promotion.level !== "info" || !await matchesScheduledRetryPromotion(db, source, promotion)) return null;
+    offset++;
+  }
   let unsupportedHarnessWarning: { message: string | null; revision: string } | null = null;
-  const warning = events[0];
+  const warning = events[offset];
   if (warning?.eventType === "agent_observability.unavailable") {
-    if (!hostEvent(warning) || warning.seq !== 1 || warning.level !== "warn"
+    if (!hostEvent(warning) || warning.seq !== 1 + offset || warning.level !== "warn"
       || warning.payload?.reason !== "unsupported_harness" || typeof warning.payload.revision !== "string" || !isUuidLike(warning.payload.revision)
       || Object.keys(warning.payload).some(key => !["reason", "revision"].includes(key))) return null;
     unsupportedHarnessWarning = { message: warning.message, revision: warning.payload.revision };
-    offset = 1;
+    offset++;
   }
   const started = events[offset];
   if (allowRunStarted && started?.eventType === "lifecycle" && started.message === "run started") {
@@ -41,3 +47,29 @@ export async function readFailedPreparationSettlement(db: Db, source: Source, al
     || !Number.isFinite(measured.payload.durationMs) || measured.payload.durationMs < 0) return null;
   return { unsupportedHarnessWarning };
 }
+
+async function matchesScheduledRetryPromotion(db: Db, source: Source, event: typeof heartbeatRunEvents.$inferSelect) {
+  const [run] = await db.select({ retryOfRunId: heartbeatRuns.retryOfRunId,
+    scheduledRetryAt: heartbeatRuns.scheduledRetryAt, scheduledRetryAttempt: heartbeatRuns.scheduledRetryAttempt,
+    scheduledRetryReason: heartbeatRuns.scheduledRetryReason,
+    retryContext: sql<Record<string, unknown>>`jsonb_build_object(
+      'retryOfRunId', ${heartbeatRuns.contextSnapshot}->'retryOfRunId',
+      'retryReason', ${heartbeatRuns.contextSnapshot}->'retryReason',
+      'scheduledRetryAt', ${heartbeatRuns.contextSnapshot}->'scheduledRetryAt',
+      'scheduledRetryAttempt', ${heartbeatRuns.contextSnapshot}->'scheduledRetryAttempt')`,
+  }).from(heartbeatRuns).where(and(eq(heartbeatRuns.companyId, source.companyId),
+    eq(heartbeatRuns.agentId, source.agentId), eq(heartbeatRuns.id, source.id)));
+  const due = run?.scheduledRetryAt?.toISOString();
+  return Boolean(run && run.retryOfRunId && isUuidLike(run.retryOfRunId) && due
+    && Number.isSafeInteger(run.scheduledRetryAttempt) && run.scheduledRetryAttempt! > 0
+    && typeof run.scheduledRetryReason === "string" && run.scheduledRetryReason.length > 0
+    && run.retryContext.retryOfRunId === run.retryOfRunId
+    && run.retryContext.retryReason === run.scheduledRetryReason
+    && run.retryContext.scheduledRetryAt === due
+    && run.retryContext.scheduledRetryAttempt === run.scheduledRetryAttempt
+    && event.createdAt >= run.scheduledRetryAt!
+    && event.payload?.scheduledRetryAt === due
+    && event.payload.scheduledRetryAttempt === run.scheduledRetryAttempt
+    && event.payload.scheduledRetryReason === run.scheduledRetryReason
+    && Object.keys(event.payload).every(key => ["scheduledRetryAt", "scheduledRetryAttempt", "scheduledRetryReason"].includes(key)));
+}
diff --git a/server/src/services/workspace-recovery-scheduled-preparation.test.ts b/server/src/services/workspace-recovery-scheduled-preparation.test.ts
new file mode 100644
index 00000000000..055e6a96ed5
--- /dev/null
+++ b/server/src/services/workspace-recovery-scheduled-preparation.test.ts
@@ -0,0 +1,101 @@
+import { randomUUID } from "node:crypto";
+import { readFile } from "node:fs/promises";
+import path from "node:path";
+import { and, eq, sql } from "drizzle-orm";
+import { agentWakeupRequests, heartbeatRunEvents, heartbeatRuns } from "@paperclipai/db";
+import type { AdapterSandboxExecutionTarget } from "@paperclipai/adapter-utils/execution-target";
+import request from "supertest";
+import { describe, expect, it, vi } from "vitest";
+import { appendHeartbeatRunEvent } from "./heartbeat-run-events.js";
+import { heartbeatService } from "./heartbeat.js";
+import { readFreshWorkspaceReadiness } from "./fresh-workspace-continuation.js";
+import { recoverRetainedWorkspace } from "./workspace-recovery.js";
+import { createSavedWorkspaceLoader } from "./remote-workspaces.js";
+import { boardRecoveryApp, db, failedRemotePreparation, receiptOnlyRecoveryApp, run, useWorkspaceRecoveryFixture } from "./__tests__/workspace-recovery-fixture.js";
+
+const targets = vi.hoisted(() => new Map<string, AdapterSandboxExecutionTarget>());
+vi.mock("./environment-execution-target.js", async importOriginal => {
+  const actual = await importOriginal<typeof import("./environment-execution-target.js")>();
+  return { ...actual, resolveEnvironmentExecutionTarget: async (input: Parameters<typeof actual.resolveEnvironmentExecutionTarget>[0]) =>
+    (input.leaseId ? targets.get(input.leaseId) : undefined) ?? actual.resolveEnvironmentExecutionTarget(input) };
+});
+
+describe("recovered scheduled preparation", () => {
+  useWorkspaceRecoveryFixture(targets);
+
+  async function scheduledPreparation(warning = false) {
+    const f = await failedRemotePreparation("retained", false, warning), source = await run(f.runId);
+    const events = await db.select().from(heartbeatRunEvents).where(eq(heartbeatRunEvents.runId, f.runId)).orderBy(heartbeatRunEvents.seq);
+    const [parent] = await db.insert(heartbeatRuns).values({ companyId: f.companyId, agentId: source.agentId,
+      issueId: f.issueId, status: "failed", finishedAt: new Date(source.createdAt.getTime() - 1000),
+      createdAt: new Date(source.createdAt.getTime() - 2000) }).returning();
+    const due = new Date(Date.now() - 1000), reason = "ai_connection_pool_wait";
+    await db.update(heartbeatRuns).set({ retryOfRunId: parent.id, scheduledRetryAt: due,
+      scheduledRetryReason: reason, scheduledRetryAttempt: 1, sessionIdBefore: randomUUID(),
+      contextSnapshot: { ...source.contextSnapshot, retryOfRunId: parent.id, retryReason: reason,
+        scheduledRetryAt: due.toISOString(), scheduledRetryAttempt: 1 },
+    }).where(eq(heartbeatRuns.id, f.runId));
+    await db.delete(heartbeatRunEvents).where(eq(heartbeatRunEvents.runId, f.runId));
+    await db.update(heartbeatRuns).set({ nextEventSeq: 1 }).where(eq(heartbeatRuns.id, f.runId));
+    await appendHeartbeatRunEvent(db, { companyId: f.companyId, runId: f.runId, agentId: source.agentId,
+      eventType: "lifecycle", stream: "system", level: "info",
+      message: "Scheduled retry became due and was promoted to the queued run pool",
+      payload: { scheduledRetryAt: due.toISOString(), scheduledRetryAttempt: 1, scheduledRetryReason: reason } });
+    for (const event of events) await appendHeartbeatRunEvent(db, { companyId: f.companyId, runId: f.runId,
+      agentId: source.agentId, eventType: event.eventType, stream: event.stream, level: event.level,
+      message: event.message, payload: event.payload });
+    await recoverRetainedWorkspace(f.input);
+    return f;
+  }
+
+  it.each([false, true])("delivers one HTTP Retry after a scheduled setup failure has recovered files (warning=%s)", async warning => {
+    const f = await scheduledPreparation(warning), source = await run(f.runId), heartbeat = heartbeatService(db);
+    const intent = { observedRunId: f.runId, idempotencyKey: randomUUID() }, app = boardRecoveryApp();
+    const receipt = (await request(app).post(`/api/issues/${f.issueId}/retry`).send(intent).expect(202)).body;
+    await Promise.all([heartbeat.resumeTaskRetry(f.companyId, receipt.requestId), heartbeat.resumeTaskRetry(f.companyId, receipt.requestId)]);
+    expect((await request(app).post(`/api/issues/${f.issueId}/retry`).send(intent).expect(202)).body.requestId).toBe(receipt.requestId);
+    const successors = await db.select().from(heartbeatRuns).where(and(eq(heartbeatRuns.companyId, f.companyId),
+      sql`${heartbeatRuns.contextSnapshot}->>'taskRetryRequestId' = ${receipt.requestId}`));
+    expect(successors).toHaveLength(1);
+    expect(successors[0]).toMatchObject({ status: "queued", contextSnapshot: { previousRunId: f.runId,
+      taskRetryRequestId: receipt.requestId, forceFreshSession: true } });
+    expect(await readFreshWorkspaceReadiness(db, successors[0])).toMatchObject({ mode: "resume_preserved_workspace" });
+    expect((await db.select().from(agentWakeupRequests).where(eq(agentWakeupRequests.id, receipt.requestId)))[0])
+      .toMatchObject({ status: "coalesced", runId: successors[0].id });
+    expect(await run(f.runId)).toEqual(source);
+    const remote = source.runnerProfileJson!.remoteWorkspace as { snapshotId: string };
+    const saved = await createSavedWorkspaceLoader(db)({ companyId: f.companyId,
+      workspaceId: f.workspaceId, snapshotId: remote.snapshotId });
+    try { expect(await readFile(path.join(saved.root, "saved.txt"), "utf8")).toBe("finished work\n"); }
+    finally { await saved.cleanup(); }
+  }, 30_000);
+
+  it.each(["attempt", "due", "reason", "context", "parent", "foreign", "provider", "extra", "controller", "stop"] as const)(
+    "retains the saved Retry when scheduled preparation proof changes: %s", async gate => {
+      const f = await scheduledPreparation(), source = await run(f.runId);
+      const receipt = (await request(receiptOnlyRecoveryApp()).post(`/api/issues/${f.issueId}/retry`)
+        .send({ observedRunId: f.runId, idempotencyKey: randomUUID() }).expect(202)).body;
+      if (["attempt", "due", "reason", "extra"].includes(gate)) await db.update(heartbeatRunEvents).set({ payload: {
+        scheduledRetryAt: (source.scheduledRetryAt!).toISOString(), scheduledRetryAttempt: 1,
+        scheduledRetryReason: source.scheduledRetryReason,
+        ...(gate === "attempt" ? { scheduledRetryAttempt: 2 } : gate === "due" ? { scheduledRetryAt: new Date(0).toISOString() }
+          : gate === "reason" ? { scheduledRetryReason: "transient_failure" } : { unknown: true }),
+      } }).where(and(eq(heartbeatRunEvents.runId, f.runId), eq(heartbeatRunEvents.seq, 1)));
+      if (gate === "context") await db.update(heartbeatRuns).set({ contextSnapshot: { ...source.contextSnapshot,
+        scheduledRetryAttempt: 2 } }).where(eq(heartbeatRuns.id, f.runId));
+      if (gate === "parent") await db.update(heartbeatRuns).set({ retryOfRunId: null }).where(eq(heartbeatRuns.id, f.runId));
+      if (gate === "foreign") await db.update(heartbeatRunEvents).set({ sourceEventId: randomUUID() })
+        .where(and(eq(heartbeatRunEvents.runId, f.runId), eq(heartbeatRunEvents.seq, 1)));
+      if (gate === "provider") await appendHeartbeatRunEvent(db, { companyId: f.companyId, runId: f.runId,
+        agentId: source.agentId, eventType: "adapter.invoke", stream: "system", message: "provider dispatch" });
+      if (gate === "controller") await db.update(heartbeatRuns).set({ controllerLeaseExpiresAt: new Date(Date.now() + 60_000) })
+        .where(eq(heartbeatRuns.id, f.runId));
+      if (gate === "stop") await db.update(heartbeatRuns).set({ resultJson: { ...source.resultJson,
+        cancellation: { source: "operator", expected: true, initiator: { type: "user", userId: "local-board" },
+          reason: "Stop", recordedAt: new Date().toISOString() } } }).where(eq(heartbeatRuns.id, f.runId));
+      await heartbeatService(db).resumeTaskRetry(f.companyId, receipt.requestId);
+      expect(await db.select().from(heartbeatRuns).where(and(eq(heartbeatRuns.companyId, f.companyId),
+        sql`${heartbeatRuns.contextSnapshot}->>'taskRetryRequestId' = ${receipt.requestId}`))).toHaveLength(0);
+      expect((await db.select().from(agentWakeupRequests).where(eq(agentWakeupRequests.id, receipt.requestId)))[0].runId).toBeNull();
+    }, 30_000);
+});