diff --git a/src/gateway/channel-health-monitor.test.ts b/src/gateway/channel-health-monitor.test.ts
index c42d8d36aa0f..399bae437b02 100644
--- a/src/gateway/channel-health-monitor.test.ts
+++ b/src/gateway/channel-health-monitor.test.ts
@@ -456,6 +456,34 @@ describe("channel-health-monitor", () => {
     monitor.stop();
   });
 
+  it("continues pending recovery on the next check without waiting for cooldown", async () => {
+    const account: Partial<ChannelAccountSnapshot> = disconnectedAccount(Date.now() - 300_000);
+    const manager = createSnapshotManager(
+      {
+        discord: {
+          default: account,
+        },
+      },
+      {
+        startChannel: vi.fn(async () => {
+          account.running = false;
+          account.connected = false;
+          account.restartPending = true;
+          account.reconnectAttempts = 0;
+        }),
+      },
+    );
+    const monitor = await startAndRunCheck(manager);
+    expect(manager.stopChannel).toHaveBeenCalledTimes(1);
+    expect(manager.startChannel).toHaveBeenCalledTimes(1);
+
+    await advanceHealthCheck();
+
+    expect(manager.stopChannel).toHaveBeenCalledTimes(1);
+    expect(manager.startChannel).toHaveBeenCalledTimes(2);
+    monitor.stop();
+  });
+
   it("caps at 3 health-monitor restarts per channel per hour", async () => {
     const manager = createSnapshotManager({
       discord: {
diff --git a/src/gateway/channel-health-monitor.ts b/src/gateway/channel-health-monitor.ts
index 7072325aa869..e3c822ced1df 100644
--- a/src/gateway/channel-health-monitor.ts
+++ b/src/gateway/channel-health-monitor.ts
@@ -145,12 +145,20 @@ export function startChannelHealthMonitor(deps: ChannelHealthMonitorDeps): Chann
             restartsThisHour: [],
           };
 
-          if (now - record.lastRestartAt <= cooldownMs) {
+          const continuingPendingRestart =
+            status.running !== true &&
+            status.restartPending === true &&
+            (status.reconnectAttempts ?? 0) === 0;
+
+          // A timed-out recovery stop uses the first start request to mark
+          // restartPending; the next monitor pass must finish that same recovery
+          // instead of waiting behind this monitor's fresh-restart cooldown.
+          if (!continuingPendingRestart && now - record.lastRestartAt <= cooldownMs) {
             continue;
           }
 
           pruneOldRestarts(record, now);
-          if (record.restartsThisHour.length >= maxRestartsPerHour) {
+          if (!continuingPendingRestart && record.restartsThisHour.length >= maxRestartsPerHour) {
             log.warn?.(
               `[${channelId}:${accountId}] health-monitor: hit ${maxRestartsPerHour} restarts/hour limit, skipping`,
             );
@@ -161,9 +169,11 @@ export function startChannelHealthMonitor(deps: ChannelHealthMonitorDeps): Chann
 
           log.info?.(`[${channelId}:${accountId}] health-monitor: restarting (reason: ${reason})`);
 
-          record.lastRestartAt = now;
-          record.restartsThisHour.push({ at: now });
-          restartRecords.set(key, record);
+          if (!continuingPendingRestart) {
+            record.lastRestartAt = now;
+            record.restartsThisHour.push({ at: now });
+            restartRecords.set(key, record);
+          }
 
           try {
             if (status.running) {