diff --git a/astrbot/core/updator.py b/astrbot/core/updator.py
index 87268c609..94cfebeb1 100644
--- a/astrbot/core/updator.py
+++ b/astrbot/core/updator.py
@@ -44,6 +44,64 @@ class AstrBotUpdator(RepoZipUpdator):
         except psutil.NoSuchProcess:
             pass
 
+    @staticmethod
+    def _is_option_arg(arg: str) -> bool:
+        return arg.startswith("-")
+
+    @classmethod
+    def _collect_flag_values(cls, argv: list[str], flag: str) -> str | None:
+        try:
+            idx = argv.index(flag)
+        except ValueError:
+            return None
+
+        if idx + 1 >= len(argv):
+            return None
+
+        value_parts: list[str] = []
+        for arg in argv[idx + 1 :]:
+            if cls._is_option_arg(arg):
+                break
+            if arg:
+                value_parts.append(arg)
+
+        if not value_parts:
+            return None
+
+        return " ".join(value_parts).strip() or None
+
+    @classmethod
+    def _resolve_webui_dir_arg(cls, argv: list[str]) -> str | None:
+        return cls._collect_flag_values(argv, "--webui-dir")
+
+    def _build_frozen_reboot_args(self) -> list[str]:
+        argv = list(sys.argv[1:])
+        webui_dir = self._resolve_webui_dir_arg(argv)
+        if not webui_dir:
+            webui_dir = os.environ.get("ASTRBOT_WEBUI_DIR")
+
+        if webui_dir:
+            return ["--webui-dir", webui_dir]
+        return []
+
+    @staticmethod
+    def _reset_pyinstaller_environment() -> None:
+        if not getattr(sys, "frozen", False):
+            return
+        os.environ["PYINSTALLER_RESET_ENVIRONMENT"] = "1"
+        for key in list(os.environ.keys()):
+            if key.startswith("_PYI_"):
+                os.environ.pop(key, None)
+
+    def _build_reboot_argv(self, executable: str) -> list[str]:
+        if os.environ.get("ASTRBOT_CLI") == "1":
+            args = sys.argv[1:]
+            return [executable, "-m", "astrbot.cli.__main__", *args]
+        if getattr(sys, "frozen", False):
+            args = self._build_frozen_reboot_args()
+            return [executable, *args]
+        return [executable, *sys.argv]
+
     def _reboot(self, delay: int = 3) -> None:
         """重启当前程序
         在指定的延迟后，终止所有子进程并重新启动程序
@@ -51,28 +109,14 @@ class AstrBotUpdator(RepoZipUpdator):
         """
         time.sleep(delay)
         self.terminate_child_processes()
-        if os.name == "nt":
-            py = f'"{sys.executable}"'
-        else:
-            py = sys.executable
+        executable = sys.executable
 
         try:
-            # 仅 CLI 模式走 `python -m astrbot.cli.__main__`，
-            # 打包后的后端可执行文件需要直接 exec 自身。
-            if os.environ.get("ASTRBOT_CLI") == "1":
-                if os.name == "nt":
-                    args = [f'"{arg}"' if " " in arg else arg for arg in sys.argv[1:]]
-                else:
-                    args = sys.argv[1:]
-                os.execl(sys.executable, py, "-m", "astrbot.cli.__main__", *args)
-            else:
-                if getattr(sys, "frozen", False):
-                    # Frozen executable should not receive argv[0] as a positional argument.
-                    os.execl(sys.executable, py, *sys.argv[1:])
-                else:
-                    os.execl(sys.executable, py, *sys.argv)
+            self._reset_pyinstaller_environment()
+            reboot_argv = self._build_reboot_argv(executable)
+            os.execv(executable, reboot_argv)
         except Exception as e:
-            logger.error(f"重启失败（{py}, {e}），请尝试手动重启。")
+            logger.error(f"重启失败（{executable}, {e}），请尝试手动重启。")
             raise e
 
     async def check_update(
diff --git a/dashboard/src/components/shared/BackupDialog.vue b/dashboard/src/components/shared/BackupDialog.vue
index cd23b691e..c69aa4464 100644
--- a/dashboard/src/components/shared/BackupDialog.vue
+++ b/dashboard/src/components/shared/BackupDialog.vue
@@ -371,6 +371,7 @@ import { ref, computed, watch } from 'vue'
 import axios from 'axios'
 import { useI18n } from '@/i18n/composables'
 import { askForConfirmation, useConfirmDialog } from '@/utils/confirmDialog'
+import { restartAstrBot as restartAstrBotRuntime } from '@/utils/restartAstrBot'
 import WaitingForRestart from './WaitingForRestart.vue'
 
 const { t } = useI18n()
@@ -948,12 +949,12 @@ const formatISODate = (isoString) => {
 }
 
 // 重启 AstrBot
-const restartAstrBot = () => {
-    axios.post('/api/stat/restart-core').then(() => {
-        if (wfr.value) {
-            wfr.value.check()
-        }
-    })
+const restartAstrBot = async () => {
+    try {
+        await restartAstrBotRuntime(wfr.value)
+    } catch (error) {
+        console.error(error)
+    }
 }
 
 // 重置所有状态
diff --git a/dashboard/src/components/shared/MigrationDialog.vue b/dashboard/src/components/shared/MigrationDialog.vue
index 445200b71..9716d8d1a 100644
--- a/dashboard/src/components/shared/MigrationDialog.vue
+++ b/dashboard/src/components/shared/MigrationDialog.vue
@@ -113,6 +113,7 @@
 import { ref, computed, watch } from 'vue'
 import axios from 'axios'
 import { useI18n } from '@/i18n/composables'
+import { restartAstrBot as restartAstrBotRuntime } from '@/utils/restartAstrBot'
 import ConsoleDisplayer from './ConsoleDisplayer.vue'
 import WaitingForRestart from './WaitingForRestart.vue'
 
@@ -258,12 +259,12 @@ const getPlatformLabel = (platform) => {
 }
 
 // 重启 AstrBot
-const restartAstrBot = () => {
-    axios.post('/api/stat/restart-core').then(() => {
-        if (wfr.value) {
-            wfr.value.check();
-        }
-    })
+const restartAstrBot = async () => {
+    try {
+        await restartAstrBotRuntime(wfr.value)
+    } catch (error) {
+        console.error(error)
+    }
 }
 
 // 打开对话框的方法
diff --git a/dashboard/src/components/shared/WaitingForRestart.vue b/dashboard/src/components/shared/WaitingForRestart.vue
index 2fbda30b2..ce97eebbd 100644
--- a/dashboard/src/components/shared/WaitingForRestart.vue
+++ b/dashboard/src/components/shared/WaitingForRestart.vue
@@ -47,6 +47,11 @@ export default {
                 this.timeoutInternal()
             }, 1000)
         },
+        stop() {
+            this.visible = false
+            this.cnt = 0
+            this.newStartTime = -1
+        },
         timeoutInternal() {
             console.log('wfr: timeoutInternal', this.newStartTime, this.startTime)
             if (this.newStartTime === -1 && this.cnt < 60 && this.visible) {
diff --git a/dashboard/src/types/electron-bridge.d.ts b/dashboard/src/types/electron-bridge.d.ts
index 9bcc18006..07676cdfc 100644
--- a/dashboard/src/types/electron-bridge.d.ts
+++ b/dashboard/src/types/electron-bridge.d.ts
@@ -11,7 +11,7 @@ declare global {
         restarting: boolean;
         canManage: boolean;
       }>;
-      restartBackend: () => Promise<{
+      restartBackend: (authToken?: string | null) => Promise<{
         ok: boolean;
         reason: string | null;
       }>;
diff --git a/dashboard/src/utils/restartAstrBot.ts b/dashboard/src/utils/restartAstrBot.ts
new file mode 100644
index 000000000..2b32c3b81
--- /dev/null
+++ b/dashboard/src/utils/restartAstrBot.ts
@@ -0,0 +1,36 @@
+import axios from 'axios'
+
+type WaitingForRestartRef = {
+  check: () => void | Promise<void>
+  stop?: () => void
+}
+
+async function triggerWaiting(waitingRef?: WaitingForRestartRef | null) {
+  if (!waitingRef) return
+  await waitingRef.check()
+}
+
+export async function restartAstrBot(
+  waitingRef?: WaitingForRestartRef | null
+): Promise<void> {
+  const desktopBridge = window.astrbotDesktop
+
+  if (desktopBridge?.isElectron) {
+    const authToken = localStorage.getItem('token')
+    try {
+      const result = await desktopBridge.restartBackend(authToken)
+      if (!result.ok) {
+        waitingRef?.stop?.()
+        throw new Error(result.reason || 'Failed to restart backend.')
+      }
+      await triggerWaiting(waitingRef)
+    } catch (error) {
+      waitingRef?.stop?.()
+      throw error
+    }
+    return
+  }
+
+  await axios.post('/api/stat/restart-core')
+  await triggerWaiting(waitingRef)
+}
diff --git a/dashboard/src/views/ConfigPage.vue b/dashboard/src/views/ConfigPage.vue
index 4b129d67b..4c27081f3 100644
--- a/dashboard/src/views/ConfigPage.vue
+++ b/dashboard/src/views/ConfigPage.vue
@@ -190,6 +190,7 @@ import WaitingForRestart from '@/components/shared/WaitingForRestart.vue';
 import StandaloneChat from '@/components/chat/StandaloneChat.vue';
 import { VueMonacoEditor } from '@guolao/vue-monaco-editor'
 import { useI18n, useModuleI18n } from '@/i18n/composables';
+import { restartAstrBot as restartAstrBotRuntime } from '@/utils/restartAstrBot';
 import {
   askForConfirmation as askForConfirmationDialog,
   useConfirmDialog
@@ -375,9 +376,7 @@ export default {
           this.save_message_success = "success";
 
           if (this.isSystemConfig) {
-            axios.post('/api/stat/restart-core').then(() => {
-              this.$refs.wfr.check();
-            })
+            restartAstrBotRuntime(this.$refs.wfr).catch(() => {})
           }
         } else {
           this.save_message = res.data.message || this.messages.saveError;
diff --git a/dashboard/src/views/Settings.vue b/dashboard/src/views/Settings.vue
index f7c401e4c..72bb2a4fb 100644
--- a/dashboard/src/views/Settings.vue
+++ b/dashboard/src/views/Settings.vue
@@ -78,12 +78,12 @@
 
 <script setup>
 import { ref, watch } from 'vue';
-import axios from 'axios';
 import WaitingForRestart from '@/components/shared/WaitingForRestart.vue';
 import ProxySelector from '@/components/shared/ProxySelector.vue';
 import MigrationDialog from '@/components/shared/MigrationDialog.vue';
 import SidebarCustomizer from '@/components/shared/SidebarCustomizer.vue';
 import BackupDialog from '@/components/shared/BackupDialog.vue';
+import { restartAstrBot as restartAstrBotRuntime } from '@/utils/restartAstrBot';
 import { useModuleI18n } from '@/i18n/composables';
 import { useTheme } from 'vuetify';
 import { PurpleTheme } from '@/theme/LightTheme';
@@ -136,10 +136,12 @@ const wfr = ref(null);
 const migrationDialog = ref(null);
 const backupDialog = ref(null);
 
-const restartAstrBot = () => {
-    axios.post('/api/stat/restart-core').then(() => {
-        wfr.value.check();
-    })
+const restartAstrBot = async () => {
+    try {
+        await restartAstrBotRuntime(wfr.value);
+    } catch (error) {
+        console.error(error);
+    }
 }
 
 const startMigration = async () => {
diff --git a/desktop/lib/backend-manager.js b/desktop/lib/backend-manager.js
index 968ee4b19..cc94f50ac 100644
--- a/desktop/lib/backend-manager.js
+++ b/desktop/lib/backend-manager.js
@@ -7,6 +7,7 @@ const { spawn, spawnSync } = require('child_process');
 const { delay, ensureDir, normalizeUrl, waitForProcessExit } = require('./common');
 
 const PACKAGED_BACKEND_TIMEOUT_FALLBACK_MS = 5 * 60 * 1000;
+const GRACEFUL_RESTART_WAIT_FALLBACK_MS = 20 * 1000;
 
 function parseBackendTimeoutMs(app) {
   const defaultTimeoutMs = app.isPackaged ? 0 : 20000;
@@ -177,6 +178,19 @@ class BackendManager {
     return this.backendConfig;
   }
 
+  getBackendPort() {
+    try {
+      const parsed = new URL(this.backendUrl);
+      if (parsed.port) {
+        const port = Number.parseInt(parsed.port, 10);
+        return Number.isFinite(port) ? port : null;
+      }
+      return parsed.protocol === 'https:' ? 443 : 80;
+    } catch {
+      return null;
+    }
+  }
+
   canManageBackend() {
     return Boolean(this.getBackendConfig().cmd);
   }
@@ -207,13 +221,124 @@ class BackendManager {
     }
   }
 
+  getEffectiveWaitMs(maxWaitMs = 0) {
+    if (maxWaitMs > 0) {
+      return maxWaitMs;
+    }
+    if (this.app.isPackaged) {
+      return PACKAGED_BACKEND_TIMEOUT_FALLBACK_MS;
+    }
+    return 0;
+  }
+
+  async requestBackendJson(pathname, options = {}) {
+    const timeoutMs = options.timeoutMs || 2000;
+    const method = options.method || 'GET';
+    const controller = new AbortController();
+    const timeout = setTimeout(() => controller.abort(), timeoutMs);
+    const requestUrl = new URL(pathname, this.backendUrl);
+    requestUrl.searchParams.set('_ts', `${Date.now()}`);
+
+    const authToken =
+      typeof options.authToken === 'string' && options.authToken
+        ? options.authToken
+        : null;
+
+    try {
+      const response = await fetch(requestUrl.toString(), {
+        method,
+        signal: controller.signal,
+        redirect: 'manual',
+        headers: {
+          Accept: 'application/json',
+          ...(authToken ? { Authorization: `Bearer ${authToken}` } : {}),
+          ...(options.headers || {}),
+        },
+      });
+      if (!response.ok) {
+        return { ok: false, data: null };
+      }
+      const data = await response.json();
+      return { ok: true, data };
+    } catch {
+      return { ok: false, data: null };
+    } finally {
+      clearTimeout(timeout);
+    }
+  }
+
+  async getBackendStartTime() {
+    const result = await this.requestBackendJson('/api/stat/start-time', {
+      timeoutMs: 1800,
+      method: 'GET',
+    });
+    if (!result.ok || !result.data) {
+      return null;
+    }
+    const rawStartTime = result.data?.data?.start_time;
+    const numericStartTime = Number(rawStartTime);
+    return Number.isFinite(numericStartTime) ? numericStartTime : null;
+  }
+
+  async requestGracefulRestart(authToken = null) {
+    const result = await this.requestBackendJson('/api/stat/restart-core', {
+      timeoutMs: 2500,
+      method: 'POST',
+      authToken,
+      headers: {
+        'Content-Type': 'application/json',
+      },
+    });
+    return result.ok;
+  }
+
+  async waitForGracefulRestart(previousStartTime, maxWaitMs = 0) {
+    const effectiveMaxWaitMs = this.getEffectiveWaitMs(maxWaitMs);
+    const gracefulWaitMs =
+      effectiveMaxWaitMs > 0
+        ? effectiveMaxWaitMs
+        : GRACEFUL_RESTART_WAIT_FALLBACK_MS;
+    const start = Date.now();
+    let sawBackendDown = false;
+
+    while (true) {
+      const reachable = await this.pingBackend(700);
+      if (!reachable) {
+        sawBackendDown = true;
+      } else {
+        const currentStartTime = await this.getBackendStartTime();
+        if (
+          previousStartTime !== null &&
+          currentStartTime !== null &&
+          currentStartTime !== previousStartTime
+        ) {
+          return { ok: true, reason: null };
+        }
+        if (sawBackendDown && previousStartTime === null) {
+          return { ok: true, reason: null };
+        }
+        if (
+          sawBackendDown &&
+          previousStartTime !== null &&
+          currentStartTime === null
+        ) {
+          return { ok: true, reason: null };
+        }
+      }
+
+      if (Date.now() - start >= gracefulWaitMs) {
+        return {
+          ok: false,
+          reason: `Timed out after ${gracefulWaitMs}ms waiting for graceful restart.`,
+        };
+      }
+
+      await delay(350);
+    }
+  }
+
   async waitForBackend(maxWaitMs = 0, failOnProcessExit = false) {
-    const effectiveMaxWaitMs =
-      maxWaitMs > 0
-        ? maxWaitMs
-        : this.app.isPackaged
-          ? PACKAGED_BACKEND_TIMEOUT_FALLBACK_MS
-          : 0;
+    const effectiveMaxWaitMs = this.getEffectiveWaitMs(maxWaitMs);
     const start = Date.now();
     while (true) {
       if (await this.pingBackend()) {
@@ -258,6 +383,9 @@ class BackendManager {
     if (this.app.isPackaged) {
       env.ASTRBOT_ELECTRON_CLIENT = '1';
     }
+    if (backendConfig.webuiDir) {
+      env.ASTRBOT_WEBUI_DIR = backendConfig.webuiDir;
+    }
     if (backendConfig.rootDir) {
       env.ASTRBOT_ROOT = backendConfig.rootDir;
       const logsDir = path.join(backendConfig.rootDir, 'logs');
@@ -344,6 +472,8 @@ class BackendManager {
 
     if (process.platform === 'win32' && pid) {
       try {
+        // Synchronous taskkill is acceptable here because stop/restart is
+        // already a control-path operation and not latency-sensitive.
         const result = spawnSync('taskkill', ['/pid', `${pid}`, '/t', '/f'], {
           stdio: 'ignore',
           windowsHide: true,
@@ -386,6 +516,115 @@ class BackendManager {
     this.closeBackendLogFd();
   }
 
+  findListeningPidsOnWindows(port) {
+    // Synchronous netstat parsing is acceptable here because this helper is
+    // used only during shutdown/restart cleanup paths.
+    const result = spawnSync('netstat', ['-ano', '-p', 'tcp'], {
+      stdio: ['ignore', 'pipe', 'ignore'],
+      encoding: 'utf8',
+      windowsHide: true,
+    });
+
+    if (result.status !== 0 || !result.stdout) {
+      return [];
+    }
+
+    const pids = new Set();
+    const lines = result.stdout.split(/\r?\n/);
+
+    for (const line of lines) {
+      const trimmed = line.trim();
+      if (!trimmed || !trimmed.toUpperCase().startsWith('TCP')) {
+        continue;
+      }
+
+      const parts = trimmed.split(/\s+/);
+      if (parts.length < 5) {
+        continue;
+      }
+
+      const localAddress = parts[1] || '';
+      const state = (parts[3] || '').toUpperCase();
+      const pid = parts[parts.length - 1];
+      if (!/^\d+$/.test(pid)) {
+        continue;
+      }
+
+      if (state !== 'LISTENING') {
+        continue;
+      }
+
+      const cleanedLocalAddress = localAddress.replace(/\]$/, '');
+      const segments = cleanedLocalAddress.split(':');
+      const portStr = segments[segments.length - 1];
+      const portNum = Number(portStr);
+      if (Number.isInteger(portNum) && portNum === Number(port)) {
+        pids.add(pid);
+      }
+    }
+
+    return Array.from(pids);
+  }
+
+  async stopUnmanagedBackendByPort() {
+    if (!this.app.isPackaged || process.platform !== 'win32') {
+      return false;
+    }
+
+    const port = this.getBackendPort();
+    if (!port) {
+      return false;
+    }
+
+    const pids = this.findListeningPidsOnWindows(port);
+    if (!pids.length) {
+      return false;
+    }
+
+    this.log(
+      `Attempting unmanaged backend cleanup by port=${port} pids=${pids.join(',')}`,
+    );
+
+    for (const pid of pids) {
+      try {
+        // Synchronous taskkill is acceptable here because unmanaged cleanup
+        // is performed only during shutdown/restart control flows.
+        spawnSync('taskkill', ['/pid', `${pid}`, '/t', '/f'], {
+          stdio: 'ignore',
+          windowsHide: true,
+        });
+      } catch {}
+    }
+
+    await delay(500);
+    return !(await this.pingBackend(1200));
+  }
+
+  async stopAnyBackend() {
+    if (this.backendProcess) {
+      await this.stopManagedBackend();
+      const running = await this.pingBackend();
+      if (!running) {
+        return { ok: true, reason: null };
+      }
+    } else {
+      const running = await this.pingBackend();
+      if (!running) {
+        return { ok: true, reason: null };
+      }
+    }
+
+    const cleaned = await this.stopUnmanagedBackendByPort();
+    if (cleaned) {
+      return { ok: true, reason: null };
+    }
+
+    return {
+      ok: false,
+      reason: 'Backend is running but not managed by Electron.',
+    };
+  }
+
   async ensureBackend() {
     this.backendStartupFailureReason = null;
 
@@ -415,7 +654,7 @@ class BackendManager {
     };
   }
 
-  async restartBackend() {
+  async restartBackend(authToken = null) {
     if (!this.canManageBackend()) {
       return {
         ok: false,
@@ -431,6 +670,31 @@ class BackendManager {
 
     this.backendRestarting = true;
     try {
+      const backendRunning = await this.pingBackend(900);
+      if (backendRunning) {
+        const previousStartTime = await this.getBackendStartTime();
+        const gracefulRequested = await this.requestGracefulRestart(authToken);
+        if (gracefulRequested) {
+          const gracefulResult = await this.waitForGracefulRestart(
+            previousStartTime,
+            this.backendTimeoutMs,
+          );
+          if (gracefulResult.ok) {
+            return {
+              ok: true,
+              reason: null,
+            };
+          }
+          this.log(
+            `Graceful restart did not complete: ${gracefulResult.reason || 'unknown reason'}`,
+          );
+        } else {
+          this.log(
+            'Graceful restart request failed; falling back to managed restart.',
+          );
+        }
+      }
+
       await this.stopManagedBackend();
       const startResult = await this.startBackendAndWait(this.backendTimeoutMs);
       if (!startResult.ok) {
@@ -468,31 +732,7 @@ class BackendManager {
     }
 
     try {
-      if (!this.backendProcess) {
-        const running = await this.pingBackend();
-        if (running) {
-          return {
-            ok: false,
-            reason: 'Backend is running but not managed by Electron.',
-          };
-        }
-        return {
-          ok: true,
-          reason: null,
-        };
-      }
-      await this.stopManagedBackend();
-      const running = await this.pingBackend();
-      if (running) {
-        return {
-          ok: false,
-          reason: 'Backend is still reachable after stop request.',
-        };
-      }
-      return {
-        ok: true,
-        reason: null,
-      };
+      return await this.stopAnyBackend();
     } catch (error) {
       return {
         ok: false,
diff --git a/desktop/main.js b/desktop/main.js
index d681f2992..0703edc7a 100644
--- a/desktop/main.js
+++ b/desktop/main.js
@@ -245,8 +245,8 @@ function registerIpcHandlers() {
     return backendManager.getState();
   });
 
-  ipcMain.handle('astrbot-desktop:restart-backend', async () => {
-    return backendManager.restartBackend();
+  ipcMain.handle('astrbot-desktop:restart-backend', async (_event, authToken) => {
+    return backendManager.restartBackend(authToken);
   });
 
   ipcMain.handle('astrbot-desktop:stop-backend', async () => {
@@ -358,12 +358,10 @@ app.on('before-quit', (event) => {
     .persistLocaleFromDashboard(mainWindow, backendManager.getBackendUrl())
     .catch(() => {})
     .then(() =>
-      backendManager.stopManagedBackend().catch((error) => {
-        logElectron(
-          `stopBackend failed: ${
-            error instanceof Error ? error.message : String(error)
-          }`,
-        );
+      backendManager.stopAnyBackend().then((result) => {
+        if (!result.ok) {
+          logElectron(`stopBackend failed: ${result.reason || 'unknown reason'}`);
+        }
       }),
     )
     .finally(() => {
diff --git a/desktop/preload.js b/desktop/preload.js
index f0fdacf34..6911a31d1 100644
--- a/desktop/preload.js
+++ b/desktop/preload.js
@@ -6,6 +6,7 @@ contextBridge.exposeInMainWorld('astrbotDesktop', {
   isElectron: true,
   isElectronRuntime: () => ipcRenderer.invoke('astrbot-desktop:is-electron-runtime'),
   getBackendState: () => ipcRenderer.invoke('astrbot-desktop:get-backend-state'),
-  restartBackend: () => ipcRenderer.invoke('astrbot-desktop:restart-backend'),
+  restartBackend: (authToken) =>
+    ipcRenderer.invoke('astrbot-desktop:restart-backend', authToken),
   stopBackend: () => ipcRenderer.invoke('astrbot-desktop:stop-backend'),
 });