diff --git a/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.test.tsx b/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.test.tsx
index 07425eb590f..54c71dd9da7 100644
--- a/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.test.tsx
+++ b/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.test.tsx
@@ -69,4 +69,20 @@ describe('EntryActionRow', () => {
     expect(text.indexOf('SecondaryNav.tsx')).toBeLessThan(text.indexOf('app/src/components/'))
     expect(container.querySelector('[data-tooltip-content]')?.textContent).toBe(filePath)
   })
+
+  it('does not duplicate the root separator for absolute root-level files', () => {
+    act(() => {
+      root.render(
+        createElement(EntryActionRow, {
+          id: 'root-file-result',
+          onClick: vi.fn(),
+          option: makeFileOption('/foo'),
+          selected: false
+        })
+      )
+    })
+
+    expect(container.querySelector('button')?.textContent).toContain('foo/')
+    expect(container.querySelector('button')?.textContent).not.toContain('foo//')
+  })
 })
diff --git a/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.tsx b/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.tsx
index eca7ae586d4..9b3a8a21eca 100644
--- a/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.tsx
+++ b/src/renderer/src/components/tab-bar/TabBarCreateEntryRow.tsx
@@ -96,7 +96,12 @@ export function EntryActionRow({
 function FilenameFirstPath({ path }: { path: string }): React.JSX.Element {
   const filename = basename(path)
   const directory = dirname(path)
-  const directoryLabel = directory === '.' ? '' : `${directory}${path.includes('\\') ? '\\' : '/'}`
+  const directoryLabel =
+    directory === '.'
+      ? ''
+      : directory.endsWith('/') || directory.endsWith('\\')
+        ? directory
+        : `${directory}${path.includes('\\') ? '\\' : '/'}`
 
   return (
     <span className="flex min-w-0 flex-1 items-center gap-1">
diff --git a/tests/e2e/tab-create-entry-file-paths.spec.ts b/tests/e2e/tab-create-entry-file-paths.spec.ts
index de32431f926..0dc97ad5920 100644
--- a/tests/e2e/tab-create-entry-file-paths.spec.ts
+++ b/tests/e2e/tab-create-entry-file-paths.spec.ts
@@ -3,7 +3,8 @@ import path from 'node:path'
 import { expect, test } from './helpers/orca-app'
 import { ensureTerminalVisible, waitForActiveWorktree, waitForSessionReady } from './helpers/store'
 
-const relativeFilePath = 'app/src/components/SecondaryNav.tsx'
+const relativeFilePath =
+  'packages/orca/src/renderer/src/components/navigation/worktree/secondary-nav/SecondaryNav.tsx'
 
 test('new-tab file results prioritize the filename and reveal the full path on hover', async ({
   orcaPage,
@@ -26,10 +27,10 @@ test('new-tab file results prioritize the filename and reveal the full path on h
   const row = orcaPage.locator('[role="option"]').filter({ hasText: 'Open file' }).first()
   await expect(row).toBeVisible()
   await expect(row).toContainText('SecondaryNav.tsx')
-  await expect(row).toContainText('app/src/components/')
+  await expect(row).toContainText('packages/orca/src/renderer/src/components/navigation/')
   const rowText = await row.textContent()
   expect(rowText?.indexOf('SecondaryNav.tsx')).toBeLessThan(
-    rowText?.indexOf('app/src/components/') ?? -1
+    rowText?.indexOf('packages/orca/src/renderer/src/components/navigation/') ?? -1
   )
 
   await row.hover({ force: true })