diff --git a/src/agents/subagent-orphan-recovery.test.ts b/src/agents/subagent-orphan-recovery.test.ts
index 7792140e3db..351e1079dc7 100644
--- a/src/agents/subagent-orphan-recovery.test.ts
+++ b/src/agents/subagent-orphan-recovery.test.ts
@@ -186,7 +186,7 @@ describe("subagent-orphan-recovery", () => {
     expect(gateway.callGateway).toHaveBeenCalledTimes(2);
   });
 
-  it("handles callGateway failure gracefully", async () => {
+  it("handles callGateway failure gracefully and preserves abortedLastRun flag", async () => {
     const sessions = await import("../config/sessions.js");
     const gateway = await import("../gateway/call.js");
 
@@ -211,6 +211,10 @@ describe("subagent-orphan-recovery", () => {
 
     expect(result.recovered).toBe(0);
     expect(result.failed).toBe(1);
+
+    // abortedLastRun flag should NOT be cleared on failure,
+    // so the next restart can retry the recovery
+    expect(sessions.updateSessionStore).not.toHaveBeenCalled();
   });
 
   it("returns empty results when no active runs exist", async () => {
@@ -246,8 +250,12 @@ describe("subagent-orphan-recovery", () => {
     expect(gateway.callGateway).not.toHaveBeenCalled();
   });
 
-  it("clears abortedLastRun flag before resuming", async () => {
+  it("clears abortedLastRun flag after successful resume", async () => {
     const sessions = await import("../config/sessions.js");
+    const gateway = await import("../gateway/call.js");
+
+    // Ensure callGateway succeeds for this test
+    vi.mocked(gateway.callGateway).mockResolvedValue({ runId: "resumed-run" } as never);
 
     vi.mocked(sessions.loadSessionStore).mockReturnValue({
       "agent:main:subagent:test-session-1": {
@@ -266,7 +274,7 @@ describe("subagent-orphan-recovery", () => {
       getActiveRuns: () => activeRuns,
     });
 
-    // updateSessionStore should have been called to clear the flag
+    // updateSessionStore should have been called AFTER successful resume to clear the flag
     expect(sessions.updateSessionStore).toHaveBeenCalledOnce();
     const calls = vi.mocked(sessions.updateSessionStore).mock.calls;
     const [storePath, updater] = calls[0];
diff --git a/src/agents/subagent-orphan-recovery.ts b/src/agents/subagent-orphan-recovery.ts
index fc30af26038..f36096d95b2 100644
--- a/src/agents/subagent-orphan-recovery.ts
+++ b/src/agents/subagent-orphan-recovery.ts
@@ -129,25 +129,31 @@ export async function recoverOrphanedSubagentSessions(params: {
 
         log.info(`found orphaned subagent session: ${childSessionKey} (run=${runId})`);
 
-        // Clear the aborted flag before resuming
-        await updateSessionStore(storePath, (currentStore) => {
-          const current = currentStore[childSessionKey];
-          if (current) {
-            current.abortedLastRun = false;
-            current.updatedAt = Date.now();
-            currentStore[childSessionKey] = current;
-          }
-        });
-
-        // Resume the session with the original task context
+        // Resume the session with the original task context.
+        // We intentionally do NOT clear abortedLastRun before attempting
+        // the resume — if callGateway fails (e.g. gateway still booting),
+        // the flag stays true so the next restart can retry.
         const resumed = await resumeOrphanedSession({
           sessionKey: childSessionKey,
           task: runRecord.task,
         });
 
         if (resumed) {
+          // Only clear the aborted flag after confirmed successful resume.
+          await updateSessionStore(storePath, (currentStore) => {
+            const current = currentStore[childSessionKey];
+            if (current) {
+              current.abortedLastRun = false;
+              current.updatedAt = Date.now();
+              currentStore[childSessionKey] = current;
+            }
+          });
           result.recovered++;
         } else {
+          // Flag stays as abortedLastRun=true so next restart can retry
+          log.warn(
+            `resume failed for ${childSessionKey}; abortedLastRun flag preserved for retry on next restart`,
+          );
           result.failed++;
         }
       } catch (err) {
diff --git a/src/agents/subagent-registry.ts b/src/agents/subagent-registry.ts
index 68fd499cbee..c1cab60dd82 100644
--- a/src/agents/subagent-registry.ts
+++ b/src/agents/subagent-registry.ts
@@ -30,7 +30,6 @@ import {
   SUBAGENT_ENDED_REASON_KILLED,
   type SubagentLifecycleEndedReason,
 } from "./subagent-lifecycle-events.js";
-import { scheduleOrphanRecovery } from "./subagent-orphan-recovery.js";
 import {
   resolveCleanupCompletionReason,
   resolveDeferredCleanupDecision,
@@ -688,10 +687,16 @@ function restoreSubagentRunsOnce() {
 
     // Schedule orphan recovery for subagent sessions that were aborted
     // by a SIGUSR1 reload. This runs after a short delay to let the
-    // gateway fully bootstrap first. (#47711)
-    scheduleOrphanRecovery({
-      getActiveRuns: () => subagentRuns,
-    });
+    // gateway fully bootstrap first. Dynamic import to avoid increasing
+    // startup memory footprint. (#47711)
+    void import("./subagent-orphan-recovery.js").then(
+      ({ scheduleOrphanRecovery }) => {
+        scheduleOrphanRecovery({ getActiveRuns: () => subagentRuns });
+      },
+      () => {
+        // Ignore import failures — orphan recovery is best-effort.
+      },
+    );
   } catch {
     // ignore restore failures
   }