diff --git a/src/app/(dashboard)/dashboard/providers/[id]/ConnectionRow.js b/src/app/(dashboard)/dashboard/providers/[id]/ConnectionRow.js
index bc97317e..d79cdc85 100644
--- a/src/app/(dashboard)/dashboard/providers/[id]/ConnectionRow.js
+++ b/src/app/(dashboard)/dashboard/providers/[id]/ConnectionRow.js
@@ -3,10 +3,10 @@
 import { useState, useEffect, useRef } from "react";
 import { getStatusVariant as getConnectionStatusVariant } from "@/shared/utils/connectionStatus";
 import PropTypes from "prop-types";
-import { Badge, Toggle } from "@/shared/components";
+import { Badge, Toggle, Tooltip } from "@/shared/components";
 import CooldownTimer from "./CooldownTimer";
 
-export default function ConnectionRow({ connection, proxyPools, isOAuth, isFirst, isLast, onMoveUp, onMoveDown, onToggleActive, onUpdateProxy, onEdit, onDelete, oneByOneStatus = null }) {
+export default function ConnectionRow({ connection, proxyPools, isOAuth, isFirst, isLast, onMoveUp, onMoveDown, onToggleActive, onUpdateProxy, onEdit, onDelete, oneByOneStatus = null, autoPing = null }) {
   const [showProxyDropdown, setShowProxyDropdown] = useState(false);
   const [updatingProxy, setUpdatingProxy] = useState(false);
   const proxyDropdownRef = useRef(null);
@@ -235,6 +235,17 @@ export default function ConnectionRow({ connection, proxyPools, isOAuth, isFirst
               )}
             </div>
           )}
+          {autoPing && (
+            <Tooltip text="When your 5h quota runs out, auto-sends a request the moment it resets so a new window starts right away.">
+              <button
+                onClick={() => autoPing.onToggle(!autoPing.on)}
+                className={`flex w-full flex-col items-center rounded px-2 py-1 transition-colors hover:bg-black/5 dark:hover:bg-white/5 ${autoPing.on ? "text-primary" : "text-text-muted hover:text-primary"}`}
+              >
+                <span className="material-symbols-outlined text-[18px]">bolt</span>
+                <span className="text-[10px] leading-tight">Auto-ping</span>
+              </button>
+            </Tooltip>
+          )}
           <button onClick={onEdit} className="flex flex-col items-center rounded px-2 py-1 text-text-muted hover:bg-black/5 hover:text-primary dark:hover:bg-white/5">
             <span className="material-symbols-outlined text-[18px]">edit</span>
             <span className="text-[10px] leading-tight">Edit</span>
@@ -288,4 +299,8 @@ ConnectionRow.propTypes = {
     state: PropTypes.string,
     error: PropTypes.string,
   }),
+  autoPing: PropTypes.shape({
+    on: PropTypes.bool,
+    onToggle: PropTypes.func,
+  }),
 };
diff --git a/src/app/(dashboard)/dashboard/providers/[id]/page.js b/src/app/(dashboard)/dashboard/providers/[id]/page.js
index ac1e808b..f9883b02 100644
--- a/src/app/(dashboard)/dashboard/providers/[id]/page.js
+++ b/src/app/(dashboard)/dashboard/providers/[id]/page.js
@@ -56,6 +56,7 @@ export default function ProviderDetailPage() {
   const [providerStrategy, setProviderStrategy] = useState(null);
   const [providerStickyLimit, setProviderStickyLimit] = useState("");
   const [thinkingMode, setThinkingMode] = useState("auto");
+  const [autoPing, setAutoPing] = useState({ enabled: false, connections: {} });
   const [suggestedModels, setSuggestedModels] = useState([]);
   const [kiloFreeModels, setKiloFreeModels] = useState([]);
   const [disabledModelIds, setDisabledModelIds] = useState([]);
@@ -258,6 +259,8 @@ export default function ProviderDetailPage() {
       // Load per-provider thinking config
       const thinkingCfg = (settingsData.providerThinking || {})[providerId] || {};
       setThinkingMode(thinkingCfg.mode || "auto");
+      const apCfg = settingsData.claudeAutoPing || {};
+      setAutoPing({ enabled: apCfg.enabled === true, connections: apCfg.connections || {} });
       if (nodesRes.ok) {
         let node = (nodesData.nodes || []).find((entry) => entry.id === providerId) || null;
 
@@ -370,6 +373,23 @@ export default function ProviderDetailPage() {
     saveThinkingConfig(mode);
   };
 
+  const saveAutoPing = async (next) => {
+    setAutoPing(next);
+    try {
+      await fetch("/api/settings", {
+        method: "PATCH",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ claudeAutoPing: next }),
+      });
+    } catch (error) {
+      console.log("Error saving auto-ping config:", error);
+    }
+  };
+
+  const handleAutoPingConnection = (connectionId, on) => {
+    saveAutoPing({ ...autoPing, connections: { ...autoPing.connections, [connectionId]: on } });
+  };
+
   useEffect(() => {
     fetchConnections();
     fetchAliases();
@@ -793,6 +813,10 @@ export default function ProviderDetailPage() {
                 onMoveUp={() => handleSwapPriority(index, index - 1)}
                 onMoveDown={() => handleSwapPriority(index, index + 1)}
                 onToggleActive={(isActive) => handleUpdateConnectionStatus(conn.id, isActive)}
+                autoPing={providerId === "claude" && conn.authType === "oauth" ? {
+                  on: autoPing.connections[conn.id] === true,
+                  onToggle: (on) => handleAutoPingConnection(conn.id, on),
+                } : null}
                 onUpdateProxy={async (proxyPoolId) => {
                   try {
                     const res = await fetch(`/api/providers/${conn.id}`, {
diff --git a/src/app/(dashboard)/dashboard/usage/components/ProviderLimits/index.js b/src/app/(dashboard)/dashboard/usage/components/ProviderLimits/index.js
index 9e4b4cc9..c82bcdda 100644
--- a/src/app/(dashboard)/dashboard/usage/components/ProviderLimits/index.js
+++ b/src/app/(dashboard)/dashboard/usage/components/ProviderLimits/index.js
@@ -50,6 +50,7 @@ export default function ProviderLimits() {
   const [loading, setLoading] = useState({});
   const [errors, setErrors] = useState({});
   const [autoRefresh, setAutoRefresh] = useState(true);
+  const [autoPingMap, setAutoPingMap] = useState({});
   const [lastUpdated, setLastUpdated] = useState(null);
   const [hasHydratedAutoRefresh, setHasHydratedAutoRefresh] = useState(false);
   const [refreshingAll, setRefreshingAll] = useState(false);
@@ -423,6 +424,31 @@ export default function ProviderLimits() {
     window.localStorage.setItem(AUTO_REFRESH_STORAGE_KEY, String(autoRefresh));
   }, [autoRefresh, hasHydratedAutoRefresh]);
 
+  // Load Claude auto-ping per-connection map
+  useEffect(() => {
+    fetch("/api/settings", { cache: "no-store" })
+      .then((r) => (r.ok ? r.json() : {}))
+      .then((s) => setAutoPingMap(s?.claudeAutoPing?.connections || {}))
+      .catch(() => {});
+  }, []);
+
+  const toggleAutoPing = useCallback(async (connectionId, on) => {
+    const next = { ...autoPingMap, [connectionId]: on };
+    setAutoPingMap(next);
+    try {
+      const r = await fetch("/api/settings", { cache: "no-store" });
+      const s = r.ok ? await r.json() : {};
+      const cfg = { ...(s.claudeAutoPing || {}), connections: next };
+      await fetch("/api/settings", {
+        method: "PATCH",
+        headers: { "Content-Type": "application/json" },
+        body: JSON.stringify({ claudeAutoPing: cfg }),
+      });
+    } catch {
+      setAutoPingMap(autoPingMap);
+    }
+  }, [autoPingMap]);
+
   // Auto-refresh interval
   useEffect(() => {
     if (!hasHydratedAutoRefresh || !autoRefresh) {
@@ -793,6 +819,7 @@ export default function ProviderLimits() {
             )}
           </button>
 
+
           {/* Refresh all button */}
           <button
             type="button"
@@ -898,6 +925,18 @@ export default function ProviderLimits() {
                         </button>
                       </Tooltip>
                     )}
+                    {conn.provider === "claude" && conn.authType === "oauth" && (
+                      <Tooltip text="When your 5h quota runs out, auto-sends a request the moment it resets so a new window starts right away.">
+                        <button
+                          type="button"
+                          onClick={() => toggleAutoPing(conn.id, !(autoPingMap[conn.id] === true))}
+                          aria-label="Toggle auto-ping"
+                          className={`flex h-8 w-8 items-center justify-center rounded-lg transition-colors hover:bg-black/5 dark:hover:bg-white/5 ${autoPingMap[conn.id] === true ? "text-primary" : "text-text-muted"}`}
+                        >
+                          <span className="material-symbols-outlined text-[18px]">bolt</span>
+                        </button>
+                      </Tooltip>
+                    )}
                     <Tooltip text="Refresh quota">
                       <button
                         type="button"
diff --git a/src/shared/constants/config.js b/src/shared/constants/config.js
index 0ed55a77..ebf5d120 100644
--- a/src/shared/constants/config.js
+++ b/src/shared/constants/config.js
@@ -62,6 +62,18 @@ export const CONSOLE_LOG_CONFIG = {
 // Client-side store TTL: how long fetched data stays fresh before re-fetching
 export const CLIENT_STORE_TTL_MS = 60000;
 
+// Claude auto-ping: keep 5h window warm by sending a tiny request right after reset
+export const CLAUDE_AUTOPING_CONFIG = {
+  settingsKey: "claudeAutoPing",        // settings table field
+  tickIntervalMs: 60000,                // scheduler tick
+  pingLeadMs: 5000,                     // fire once reset passes (within tolerance)
+  pingModel: "claude-haiku-4-5-20251001", // cheapest model
+  pingText: "hi",
+  pingMaxTokens: 1,
+  refreshAheadMs: 300000,               // refetch usage when within 5min of reset
+  fiveHourKey: "session (5h)",          // quota key returned by usage handler
+};
+
 // Re-export from providers.js for backward compatibility
 export {
   FREE_PROVIDERS,
diff --git a/src/shared/services/claudeAutoPing.js b/src/shared/services/claudeAutoPing.js
new file mode 100644
index 00000000..d7e5148c
--- /dev/null
+++ b/src/shared/services/claudeAutoPing.js
@@ -0,0 +1,110 @@
+// Claude auto-ping scheduler: warms the 5h window by sending a tiny request right after reset.
+import "open-sse/index.js";
+
+import { getSettings, getProviderConnections, updateProviderConnection } from "@/lib/localDb";
+import { getClaudeUsage } from "open-sse/services/usage/claude.js";
+import { CLAUDE_CLI_SPOOF_HEADERS } from "open-sse/providers/shared.js";
+import { proxyAwareFetch } from "open-sse/utils/proxyFetch.js";
+import { resolveConnectionProxyConfig } from "@/lib/network/connectionProxy";
+import { refreshAndUpdateCredentials } from "@/app/api/usage/[connectionId]/route.js";
+import { CLAUDE_AUTOPING_CONFIG } from "@/shared/constants/config";
+
+const C = CLAUDE_AUTOPING_CONFIG;
+const PING_URL = "https://api.anthropic.com/v1/messages?beta=true";
+
+const g = (global.__claudeAutoPing ??= { interval: null, running: false });
+
+function buildProxyOptions(cfg) {
+  return {
+    connectionProxyEnabled: cfg.connectionProxyEnabled === true,
+    connectionProxyUrl: cfg.connectionProxyUrl || "",
+    connectionNoProxy: cfg.connectionNoProxy || "",
+    vercelRelayUrl: cfg.vercelRelayUrl || "",
+    strictProxy: false,
+  };
+}
+
+// Send minimal "hi" to start a fresh 5h window
+async function sendPing(accessToken, proxyOptions) {
+  const res = await proxyAwareFetch(PING_URL, {
+    method: "POST",
+    headers: {
+      ...CLAUDE_CLI_SPOOF_HEADERS,
+      "Authorization": `Bearer ${accessToken}`,
+      "content-type": "application/json",
+    },
+    body: JSON.stringify({
+      model: C.pingModel,
+      max_tokens: C.pingMaxTokens,
+      messages: [{ role: "user", content: C.pingText }],
+    }),
+  }, proxyOptions);
+  return res.ok;
+}
+
+async function pingConnection(conn) {
+  const proxyCfg = await resolveConnectionProxyConfig(conn.providerSpecificData);
+  const proxyOptions = buildProxyOptions(proxyCfg);
+
+  // Refresh token if needed, then read 5h reset time
+  let connection = conn;
+  try {
+    const r = await refreshAndUpdateCredentials(connection, false, proxyOptions);
+    connection = r.connection;
+  } catch (e) {
+    console.warn(`[AutoPing] ${conn.id}: refresh failed: ${e.message}`);
+    return;
+  }
+
+  const usage = await getClaudeUsage(connection.accessToken, proxyOptions);
+  const resetAt = usage?.quotas?.[C.fiveHourKey]?.resetAt;
+  if (!resetAt) return;
+
+  const resetMs = new Date(resetAt).getTime();
+  const now = Date.now();
+
+  // Only ping once per reset cycle, right after window flips
+  if (now < resetMs - C.pingLeadMs) return;
+  if (connection.lastPingedResetAt === resetAt) return;
+
+  const ok = await sendPing(connection.accessToken, proxyOptions);
+  await updateProviderConnection(connection.id, {
+    lastPingedResetAt: resetAt,
+    lastPingAt: new Date().toISOString(),
+    updatedAt: new Date().toISOString(),
+  });
+  console.log(`[AutoPing] ${connection.id}: ping ${ok ? "sent" : "failed"} (reset ${resetAt})`);
+}
+
+async function tick() {
+  if (g.running) return;
+  g.running = true;
+  try {
+    const settings = await getSettings();
+    const enabledMap = settings[C.settingsKey]?.connections || {};
+    if (Object.keys(enabledMap).length === 0) return;
+
+    const conns = await getProviderConnections({ provider: "claude", isActive: true });
+    // Only ping connections the user explicitly enabled
+    const targets = conns.filter((c) => c.authType === "oauth" && enabledMap[c.id] === true);
+    if (targets.length === 0) return;
+
+    for (const conn of targets) {
+      try {
+        await pingConnection(conn);
+      } catch (e) {
+        console.warn(`[AutoPing] ${conn.id}: ${e.message}`);
+      }
+    }
+  } catch (e) {
+    console.warn("[AutoPing] tick error:", e.message);
+  } finally {
+    g.running = false;
+  }
+}
+
+export function startClaudeAutoPing() {
+  if (g.interval) return;
+  g.interval = setInterval(() => { tick().catch(() => {}); }, C.tickIntervalMs);
+  if (g.interval.unref) g.interval.unref();
+}
diff --git a/src/shared/services/initializeApp.js b/src/shared/services/initializeApp.js
index 3f79f66a..234c90d6 100644
--- a/src/shared/services/initializeApp.js
+++ b/src/shared/services/initializeApp.js
@@ -14,6 +14,7 @@ import {
   WATCHDOG_INTERVAL_MS, NETWORK_CHECK_INTERVAL_MS, VIRTUAL_IFACE_REGEX,
 } from "@/lib/tunnel";
 import { getMitmStatus, startMitm, loadEncryptedPassword, initDbHooks, restoreToolDNS, removeAllDNSEntriesSync } from "@/mitm/manager";
+import { startClaudeAutoPing } from "@/shared/services/claudeAutoPing";
 import { syncToJson as syncMitmAliasCache } from "@/lib/mitmAliasCache";
 
 // Inject correct paths and DB hooks into manager.js (CJS) from ESM context
@@ -88,6 +89,7 @@ export async function initializeApp() {
     startWatchdog();
     startNetworkMonitor();
     autoStartMitm();
+    startClaudeAutoPing();
   } catch (error) {
     console.error("[InitApp] Error:", error);
   }