diff --git a/pkg/tui/dialog/file_picker.go b/pkg/tui/dialog/file_picker.go
index 20db586c5..4c02e4db0 100644
--- a/pkg/tui/dialog/file_picker.go
+++ b/pkg/tui/dialog/file_picker.go
@@ -144,7 +144,7 @@ func (d *filePickerDialog) loadDirectory() {
 	d.scrollview.SetScrollOffset(0)
 	d.err = nil
 
-	if d.currentDir != "/" {
+	if filepath.Dir(d.currentDir) != d.currentDir {
 		d.entries = append(d.entries, fileEntry{
 			name:  "..",
 			path:  filepath.Dir(d.currentDir),
diff --git a/pkg/tui/dialog/working_dir_picker.go b/pkg/tui/dialog/working_dir_picker.go
index f2f1ba4bf..30af95d41 100644
--- a/pkg/tui/dialog/working_dir_picker.go
+++ b/pkg/tui/dialog/working_dir_picker.go
@@ -168,7 +168,7 @@ func NewWorkingDirPickerDialog(ctx context.Context, recentDirs, favoriteDirs []s
 		var err error
 		cwd, err = os.Getwd()
 		if err != nil {
-			cwd = "/"
+			cwd = "."
 		}
 	}
 
@@ -258,7 +258,7 @@ func (d *workingDirPickerDialog) loadBrowseDirectory() {
 		kind: entryUseThisDir,
 	})
 
-	if d.currentDir != "/" {
+	if filepath.Dir(d.currentDir) != d.currentDir {
 		d.browseEntries = append(d.browseEntries, dirEntry{
 			name: "..",
 			path: filepath.Dir(d.currentDir),
diff --git a/pkg/tui/tui.go b/pkg/tui/tui.go
index 5dff84ce8..278afd5aa 100644
--- a/pkg/tui/tui.go
+++ b/pkg/tui/tui.go
@@ -1999,7 +1999,7 @@ func (m *appModel) handleCloseTab(sessionID string) (tea.Model, tea.Cmd) {
 			workingDir, _ = os.Getwd()
 		}
 		if workingDir == "" {
-			workingDir = "/"
+			workingDir = "."
 		}
 		return m.handleSpawnSession(workingDir)
 	}