diff --git a/packages/app/e2e/helpers/app.ts b/packages/app/e2e/helpers/app.ts
index 71e505a6c..e3f7efea9 100644
--- a/packages/app/e2e/helpers/app.ts
+++ b/packages/app/e2e/helpers/app.ts
@@ -367,7 +367,7 @@ export const createAgent = async (page: Page, message: string) => {
   await input.press('Enter');
 
   // Router updates can be same-document transitions; assert URL state instead of waiting for a commit event.
-  await expect(page).toHaveURL(/\/agent\//, { timeout: 30000 });
+  await expect(page).toHaveURL(/\/(workspace|agent)\//, { timeout: 30000 });
   await expect(page.getByText(message, { exact: true }).first()).toBeVisible({
     timeout: 30000,
   });
diff --git a/packages/app/e2e/workspace-sidebar-content-sync.spec.ts b/packages/app/e2e/workspace-sidebar-content-sync.spec.ts
new file mode 100644
index 000000000..a7bb1e6dd
--- /dev/null
+++ b/packages/app/e2e/workspace-sidebar-content-sync.spec.ts
@@ -0,0 +1,103 @@
+import { execSync } from 'node:child_process';
+import { test, expect, type Page } from './fixtures';
+import { setWorkingDirectory } from './helpers/app';
+import { createTempGitRepo } from './helpers/workspace';
+import { buildHostWorkspaceRoute } from '@/utils/host-routes';
+
+function escapeRegex(value: string): string {
+  return value.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+}
+
+function candidateWorkspaceIds(inputPath: string): string[] {
+  const trimmed = inputPath.replace(/\/+$/, '');
+  const candidates = new Set<string>([trimmed]);
+  if (trimmed.startsWith('/var/')) {
+    candidates.add(`/private${trimmed}`);
+  }
+  if (trimmed.startsWith('/private/var/')) {
+    candidates.add(trimmed.replace(/^\/private/, ''));
+  }
+  return Array.from(candidates);
+}
+
+function workspaceRowLocator(page: Page, serverId: string, workspacePath: string) {
+  const ids = candidateWorkspaceIds(workspacePath).map(
+    (id) => `[data-testid="sidebar-workspace-row-${serverId}:${id}"]`
+  );
+  return page.locator(ids.join(',')).first();
+}
+
+async function openNewAgentComposer(page: Page): Promise<void> {
+  await page.goto('/');
+
+  const sidebarNewAgent = page.getByTestId('sidebar-new-agent').first();
+  if (await sidebarNewAgent.isVisible().catch(() => false)) {
+    await sidebarNewAgent.click();
+  } else {
+    await page.getByText('New agent', { exact: true }).first().click();
+  }
+
+  await expect(page.getByRole('textbox', { name: 'Message agent...' })).toBeVisible({ timeout: 30000 });
+}
+
+async function seedWorkspaceActivity(page: Page, marker: string): Promise<void> {
+  const input = page.getByRole('textbox', { name: 'Message agent...' });
+  await expect(input).toBeEditable({ timeout: 30000 });
+  await input.fill(marker);
+  await input.press('Enter');
+  await expect(page).toHaveURL(/\/workspace\//, { timeout: 30000 });
+}
+
+async function switchViaSidebar(input: {
+  page: Page;
+  serverId: string;
+  targetWorkspacePath: string;
+}) {
+  const row = workspaceRowLocator(input.page, input.serverId, input.targetWorkspacePath);
+  await expect(row).toBeVisible({ timeout: 30000 });
+  await row.click();
+
+  const targetWorkspaceRoute = buildHostWorkspaceRoute(input.serverId, input.targetWorkspacePath);
+  await expect(input.page).toHaveURL(new RegExp(escapeRegex(targetWorkspaceRoute)), {
+    timeout: 30000,
+  });
+}
+
+test('sidebar workspace switch keeps visible content in sync with selected workspace', async ({ page }) => {
+  const serverId = process.env.E2E_SERVER_ID;
+  if (!serverId) {
+    throw new Error('E2E_SERVER_ID is not set.');
+  }
+
+  const repoA = await createTempGitRepo('paseo-e2e-sync-a-');
+  const repoB = await createTempGitRepo('paseo-e2e-sync-b-');
+
+  const tokenA = `SYNC_A_${Date.now()}`;
+  const tokenB = `SYNC_B_${Date.now()}`;
+
+  try {
+    execSync('git checkout -b sync-a-branch', { cwd: repoA.path, stdio: 'ignore' });
+    execSync('git checkout -b sync-b-branch', { cwd: repoB.path, stdio: 'ignore' });
+
+    await openNewAgentComposer(page);
+    await setWorkingDirectory(page, repoA.path);
+    await seedWorkspaceActivity(page, tokenA);
+
+    await openNewAgentComposer(page);
+    await setWorkingDirectory(page, repoB.path);
+    await seedWorkspaceActivity(page, tokenB);
+
+    await page.goto(buildHostWorkspaceRoute(serverId, repoA.path));
+    await expect(page).toHaveURL(new RegExp('/workspace/'), { timeout: 30000 });
+    await expect(page.getByText('sync-a-branch', { exact: true }).first()).toBeVisible({ timeout: 30000 });
+
+    await switchViaSidebar({ page, serverId, targetWorkspacePath: repoB.path });
+    await expect(page.getByText('sync-b-branch', { exact: true }).first()).toBeVisible({ timeout: 30000 });
+
+    await switchViaSidebar({ page, serverId, targetWorkspacePath: repoA.path });
+    await expect(page.getByText('sync-a-branch', { exact: true }).first()).toBeVisible({ timeout: 30000 });
+  } finally {
+    await repoA.cleanup();
+    await repoB.cleanup();
+  }
+});
diff --git a/packages/app/src/components/sidebar-workspace-list.tsx b/packages/app/src/components/sidebar-workspace-list.tsx
index 2437debbe..ce7b53350 100644
--- a/packages/app/src/components/sidebar-workspace-list.tsx
+++ b/packages/app/src/components/sidebar-workspace-list.tsx
@@ -792,7 +792,7 @@ function ProjectBlock({
               return
             }
             onWorkspacePress?.()
-            router.push(workspaceRoute as any)
+            router.replace(workspaceRoute as any)
           }}
           drag={workspaceDrag}
           isDragging={isActive}