diff --git a/config/test-suites.ts b/config/test-suites.ts
index 3a16ed1a..c440ce65 100644
--- a/config/test-suites.ts
+++ b/config/test-suites.ts
@@ -63,6 +63,7 @@ export const BROWSER_TEST_GLOBS = [
   'test/desktop-connect-page.browser.test.ts', // no server: the page is served by request interception
   'test/local-model-ui.browser.test.ts',
   'test/home-breakpoint-swap.browser.test.ts',
+  'test/log-viewer-reconnect.browser.test.ts',
 ];
 
 /**
diff --git a/src/web/public/panels-ui.js b/src/web/public/panels-ui.js
index 662bfefe..2c503f9d 100644
--- a/src/web/public/panels-ui.js
+++ b/src/web/public/panels-ui.js
@@ -6163,6 +6163,7 @@ Object.assign(CodemanApp.prototype, {
       CodemanBase.url(`/api/sessions/${sessionId}/tail-file?path=${encodeURIComponent(filePath)}&lines=50`)
     );
 
+    let connected = false;
     eventSource.onmessage = (e) => {
       const data = JSON.parse(e.data);
       const body = document.getElementById(`log-viewer-body-${windowId}`);
@@ -6170,6 +6171,7 @@ Object.assign(CodemanApp.prototype, {
 
       switch (data.type) {
         case 'connected':
+          connected = true;
           body.innerHTML = '';
           break;
         case 'data':
@@ -6189,6 +6191,7 @@ Object.assign(CodemanApp.prototype, {
           this.updateLogViewerStatus(windowId, 'disconnected', 'ended');
           break;
         case 'error':
+          if (!connected) eventSource.close();
           body.innerHTML += `<div class="log-error">${escapeHtml(data.error)}</div>`;
           this.updateLogViewerStatus(windowId, 'error', 'error');
           break;
diff --git a/test/log-viewer-reconnect.browser.test.ts b/test/log-viewer-reconnect.browser.test.ts
new file mode 100644
index 00000000..9f60f5fb
--- /dev/null
+++ b/test/log-viewer-reconnect.browser.test.ts
@@ -0,0 +1,59 @@
+import { afterAll, beforeAll, describe, expect, it } from 'vitest';
+import { chromium, type Browser } from 'playwright';
+import { WebServer } from '../src/web/server.js';
+
+const id = 'log-reconnect-fixture',
+  path = '/workspace/demo.log';
+describe('log viewer pre-connect failures', () => {
+  let server: WebServer, browser: Browser;
+  beforeAll(async () => {
+    server = new WebServer(0, false, true);
+    await server.start();
+    browser = await chromium.launch({ headless: true });
+  }, 60000);
+  afterAll(async () => {
+    await browser?.close();
+    await server?.stop();
+  });
+  it.each([
+    'Path must be within working directory or allowed log directories',
+    'File does not exist',
+    'File not found or not accessible',
+    'File too large',
+    'Maximum 5 concurrent streams per session',
+    'Failed to spawn tail process',
+  ])('does not reconnect after %s before connected', async (error) => {
+    const page = await browser.newPage(),
+      errors: string[] = [];
+    let requests = 0;
+    page.on('pageerror', (e) => errors.push(e.message));
+    await page.route(`**/api/sessions/${id}/tail-file?**`, async (route) => {
+      requests++;
+      return route.fulfill({
+        status: 200,
+        contentType: 'text/event-stream',
+        // retry: 200 makes a reconnect, if one came, show up within 200 ms.
+        body: `retry: 200\ndata: ${JSON.stringify({ type: 'error', error })}\n\n`,
+      });
+    });
+    try {
+      await page.goto(`http://127.0.0.1:${server.boundPort}`, { waitUntil: 'domcontentloaded' });
+      await page.waitForFunction(() => (window as any).app?.openLogViewerWindow);
+      await page.waitForTimeout(3500);
+      await page.evaluate(
+        ({ id, path }) => {
+          const app = (window as any).app;
+          app.sessions.set(id, { id, mode: 'shell', workingDir: '/workspace' });
+          app.openLogViewerWindow(path, id);
+        },
+        { id, path }
+      );
+      await expect.poll(() => page.locator('.log-viewer-window').innerText()).toContain(error);
+      await page.waitForTimeout(1000);
+      expect(requests).toBe(1);
+      expect(errors).toEqual([]);
+    } finally {
+      await page.close();
+    }
+  });
+});