diff --git a/src/web-server/routes/cliproxy-stats-routes.ts b/src/web-server/routes/cliproxy-stats-routes.ts
index 4b082730..4f92fc38 100644
--- a/src/web-server/routes/cliproxy-stats-routes.ts
+++ b/src/web-server/routes/cliproxy-stats-routes.ts
@@ -34,11 +34,7 @@ import {
 } from '../../cliproxy/config-generator';
 import { getProxyStatus as getProxyProcessStatus, stopProxy } from '../../cliproxy/session-tracker';
 import { ensureCliproxyService } from '../../cliproxy/service-manager';
-import {
-  checkCliproxyUpdate,
-  getInstalledCliproxyVersion,
-  installCliproxyVersion,
-} from '../../cliproxy/binary-manager';
+import { checkCliproxyUpdate, getInstalledCliproxyVersion } from '../../cliproxy/binary-manager';
 import {
   fetchAllVersions,
   isNewerVersion,
@@ -56,6 +52,7 @@ import {
   canonicalizeModelIdForProvider,
   getDeniedModelIdReasonForProvider,
 } from '../../cliproxy/model-id-normalizer';
+import { installDashboardCliproxyVersion } from '../services/cliproxy-dashboard-install-service';
 
 const router = Router();
 
@@ -928,7 +925,7 @@ router.get('/versions', async (_req: Request, res: Response): Promise<void> => {
 /**
  * POST /api/cliproxy/install - Install specific CLIProxyAPI version
  * Body: { version: string, force?: boolean }
- * Returns: { success, requiresConfirmation?, message? }
+ * Returns: { success, restarted?, port?, requiresConfirmation?, message? }
  */
 router.post('/install', async (req: Request, res: Response): Promise<void> => {
   try {
@@ -967,22 +964,14 @@ router.post('/install', async (req: Request, res: Response): Promise<void> => {
       return;
     }
 
-    // Stop proxy first if running
-    await stopProxy();
-
-    // Small delay to ensure port is released
-    await new Promise((r) => setTimeout(r, 500));
-
-    // Install the version
     const backend = getConfiguredBackend();
-    await installCliproxyVersion(version, true, backend);
+    const installResult = await installDashboardCliproxyVersion(version, backend);
 
     res.json({
-      success: true,
       version,
       isFaulty,
       isExperimental,
-      message: `Successfully installed CLIProxy Plus v${version}`,
+      ...installResult,
     });
   } catch (error) {
     console.error(`[cliproxy-stats] ${(error as Error).message}`);
diff --git a/src/web-server/services/cliproxy-dashboard-install-service.ts b/src/web-server/services/cliproxy-dashboard-install-service.ts
new file mode 100644
index 00000000..cb96487d
--- /dev/null
+++ b/src/web-server/services/cliproxy-dashboard-install-service.ts
@@ -0,0 +1,80 @@
+import { installCliproxyVersion } from '../../cliproxy/binary-manager';
+import { ensureCliproxyService, type ServiceStartResult } from '../../cliproxy/service-manager';
+import { getProxyStatus as getProxyProcessStatus } from '../../cliproxy/session-tracker';
+import { isCliproxyRunning } from '../../cliproxy/stats-fetcher';
+import type { CLIProxyBackend } from '../../cliproxy/types';
+
+interface ProxyStatusLike {
+  running: boolean;
+}
+
+interface InstallDashboardCliproxyVersionDeps {
+  getProxyStatus: () => ProxyStatusLike;
+  isCliproxyRunning: () => Promise<boolean>;
+  installCliproxyVersion: (
+    version: string,
+    verbose?: boolean,
+    backend?: CLIProxyBackend
+  ) => Promise<void>;
+  ensureCliproxyService: () => Promise<ServiceStartResult>;
+}
+
+const defaultDeps: InstallDashboardCliproxyVersionDeps = {
+  getProxyStatus: getProxyProcessStatus,
+  isCliproxyRunning,
+  installCliproxyVersion,
+  ensureCliproxyService: () => ensureCliproxyService(),
+};
+
+export interface DashboardCliproxyInstallResult {
+  success: boolean;
+  restarted: boolean;
+  port?: number;
+  message: string;
+  error?: string;
+}
+
+async function wasProxyRunning(deps: InstallDashboardCliproxyVersionDeps): Promise<boolean> {
+  const status = deps.getProxyStatus();
+  if (status.running) {
+    return true;
+  }
+
+  return deps.isCliproxyRunning();
+}
+
+export async function installDashboardCliproxyVersion(
+  version: string,
+  backend: CLIProxyBackend,
+  deps: InstallDashboardCliproxyVersionDeps = defaultDeps
+): Promise<DashboardCliproxyInstallResult> {
+  const backendLabel = backend === 'plus' ? 'CLIProxy Plus' : 'CLIProxy';
+  const shouldRestoreService = await wasProxyRunning(deps);
+
+  await deps.installCliproxyVersion(version, true, backend);
+
+  if (!shouldRestoreService) {
+    return {
+      success: true,
+      restarted: false,
+      message: `Successfully installed ${backendLabel} v${version}`,
+    };
+  }
+
+  const startResult = await deps.ensureCliproxyService();
+  if (!startResult.started && !startResult.alreadyRunning) {
+    return {
+      success: false,
+      restarted: false,
+      error: startResult.error || `Installed ${backendLabel} v${version}, but restart failed`,
+      message: `Installed ${backendLabel} v${version}, but failed to restart it`,
+    };
+  }
+
+  return {
+    success: true,
+    restarted: true,
+    port: startResult.port,
+    message: `Successfully installed ${backendLabel} v${version} and restarted it on port ${startResult.port}`,
+  };
+}
diff --git a/tests/unit/web-server/cliproxy-dashboard-install-service.test.ts b/tests/unit/web-server/cliproxy-dashboard-install-service.test.ts
new file mode 100644
index 00000000..9af88014
--- /dev/null
+++ b/tests/unit/web-server/cliproxy-dashboard-install-service.test.ts
@@ -0,0 +1,105 @@
+import { describe, expect, it } from 'bun:test';
+import type { CLIProxyBackend } from '../../../src/cliproxy/types';
+import {
+  installDashboardCliproxyVersion,
+  type DashboardCliproxyInstallResult,
+} from '../../../src/web-server/services/cliproxy-dashboard-install-service';
+
+function createDeps(
+  overrides: {
+    sessionRunning?: boolean;
+    remoteRunning?: boolean;
+    startResult?: { started: boolean; alreadyRunning: boolean; port: number; error?: string };
+  } = {}
+) {
+  const calls = {
+    isCliproxyRunning: 0,
+    installCliproxyVersion: 0,
+    ensureCliproxyService: 0,
+  };
+
+  const deps = {
+    getProxyStatus: () => ({ running: overrides.sessionRunning ?? false }),
+    isCliproxyRunning: async () => {
+      calls.isCliproxyRunning += 1;
+      return overrides.remoteRunning ?? false;
+    },
+    installCliproxyVersion: async (
+      _version: string,
+      _verbose?: boolean,
+      _backend?: CLIProxyBackend
+    ) => {
+      calls.installCliproxyVersion += 1;
+    },
+    ensureCliproxyService: async () => {
+      calls.ensureCliproxyService += 1;
+      return (
+        overrides.startResult ?? {
+          started: true,
+          alreadyRunning: false,
+          port: 8317,
+        }
+      );
+    },
+  };
+
+  return { deps, calls };
+}
+
+describe('installDashboardCliproxyVersion', () => {
+  it('restarts the proxy after install when it was already running', async () => {
+    const { deps, calls } = createDeps({ sessionRunning: true });
+
+    const result = await installDashboardCliproxyVersion('6.7.1', 'plus', deps);
+
+    expect(result).toEqual<DashboardCliproxyInstallResult>({
+      success: true,
+      restarted: true,
+      port: 8317,
+      message: 'Successfully installed CLIProxy Plus v6.7.1 and restarted it on port 8317',
+    });
+    expect(calls.isCliproxyRunning).toBe(0);
+    expect(calls.installCliproxyVersion).toBe(1);
+    expect(calls.ensureCliproxyService).toBe(1);
+  });
+
+  it('keeps the proxy stopped after install when it was not running beforehand', async () => {
+    const { deps, calls } = createDeps({ sessionRunning: false, remoteRunning: false });
+
+    const result = await installDashboardCliproxyVersion('6.7.1', 'plus', deps);
+
+    expect(result).toEqual<DashboardCliproxyInstallResult>({
+      success: true,
+      restarted: false,
+      message: 'Successfully installed CLIProxy Plus v6.7.1',
+    });
+    expect(calls.isCliproxyRunning).toBe(1);
+    expect(calls.installCliproxyVersion).toBe(1);
+    expect(calls.ensureCliproxyService).toBe(0);
+  });
+
+  it('reports a restart failure after a successful install when the proxy had been running', async () => {
+    const { deps, calls } = createDeps({
+      sessionRunning: false,
+      remoteRunning: true,
+      startResult: {
+        started: false,
+        alreadyRunning: false,
+        port: 8317,
+        error: 'Port 8317 is blocked by another process',
+      },
+    });
+
+    const result = await installDashboardCliproxyVersion('6.7.1', 'original', deps);
+
+    expect(result).toEqual<DashboardCliproxyInstallResult>({
+      success: false,
+      restarted: false,
+      error: 'Port 8317 is blocked by another process',
+      message: 'Installed CLIProxy v6.7.1, but failed to restart it',
+    });
+    expect(calls.isCliproxyRunning).toBe(1);
+    expect(calls.installCliproxyVersion).toBe(1);
+    expect(calls.ensureCliproxyService).toBe(1);
+  });
+});
diff --git a/ui/src/lib/api-client.ts b/ui/src/lib/api-client.ts
index 5f581f2f..607873fa 100644
--- a/ui/src/lib/api-client.ts
+++ b/ui/src/lib/api-client.ts
@@ -606,6 +606,8 @@ export interface CliproxyVersionsResponse {
 export interface CliproxyInstallResult {
   success: boolean;
   version?: string;
+  restarted?: boolean;
+  port?: number;
   isUnstable?: boolean;
   requiresConfirmation?: boolean;
   message?: string;