diff --git a/webui/backend/tests/golden/__pycache__/test_ui_smoke_golden.cpython-313.pyc b/webui/backend/tests/golden/__pycache__/test_ui_smoke_golden.cpython-313.pyc
index 822f628..63cb2b1 100644
Binary files a/webui/backend/tests/golden/__pycache__/test_ui_smoke_golden.cpython-313.pyc and b/webui/backend/tests/golden/__pycache__/test_ui_smoke_golden.cpython-313.pyc differ
diff --git a/webui/backend/tests/golden/test_ui_smoke_golden.py b/webui/backend/tests/golden/test_ui_smoke_golden.py
index fdbf96e..5b67d96 100644
--- a/webui/backend/tests/golden/test_ui_smoke_golden.py
+++ b/webui/backend/tests/golden/test_ui_smoke_golden.py
@@ -213,6 +213,7 @@ class UiSmokeGoldenTest(unittest.TestCase):
         self.assertIn('function contextMenuElements()', app_js)
         self.assertIn('function openContextMenu(pane, entry, event)', app_js)
         self.assertIn('function closeContextMenu()', app_js)
+        self.assertIn('function isOpenableSelection(item)', app_js)
         self.assertIn('function applyContextMenuSelection()', app_js)
         self.assertIn('function startContextMenuOpen()', app_js)
         self.assertIn('function startContextMenuEdit()', app_js)
@@ -228,7 +229,10 @@ class UiSmokeGoldenTest(unittest.TestCase):
         self.assertIn('if (!row) {', app_js)
         self.assertIn('closeContextMenu();', app_js)
         self.assertIn('elements.openButton.classList.toggle("hidden", isMulti);', app_js)
-        self.assertIn('elements.openButton.disabled = isMulti || items.length !== 1;', app_js)
+        self.assertIn('const openableSingle = items.length === 1 && isOpenableSelection(items[0]);', app_js)
+        self.assertIn('elements.openButton.disabled = !openableSingle;', app_js)
+        self.assertIn('if (item.kind === "directory") {', app_js)
+        self.assertIn('return isImageSelection(item) || isVideoSelection(item);', app_js)
         self.assertIn('const editableSingle = items.length === 1 && isEditableSelection(items[0]);', app_js)
         self.assertIn('elements.editButton.classList.toggle("hidden", isMulti || items.length !== 1 || items[0].kind !== "file");', app_js)
         self.assertIn('elements.editButton.disabled = !editableSingle;', app_js)
diff --git a/webui/html/app.js b/webui/html/app.js
index b6f6bdc..b06523d 100644
--- a/webui/html/app.js
+++ b/webui/html/app.js
@@ -336,6 +336,16 @@ function contextMenuElements() {
   };
 }
 
+function isOpenableSelection(item) {
+  if (!item) {
+    return false;
+  }
+  if (item.kind === "directory") {
+    return true;
+  }
+  return isImageSelection(item) || isVideoSelection(item);
+}
+
 function isContextMenuOpen() {
   return contextMenuState.open && !contextMenuElements().menu.classList.contains("hidden");
 }
@@ -371,11 +381,12 @@ function openContextMenu(pane, entry, event) {
   contextMenuState.anchorPath = entry.path;
 
   const isMulti = items.length > 1;
+  const openableSingle = items.length === 1 && isOpenableSelection(items[0]);
   const editableSingle = items.length === 1 && isEditableSelection(items[0]);
   elements.scope.textContent = isMulti ? "Multi-selection" : "Single item";
   elements.target.textContent = isMulti ? `${items.length} selected items` : entry.name;
   elements.openButton.classList.toggle("hidden", isMulti);
-  elements.openButton.disabled = isMulti || items.length !== 1;
+  elements.openButton.disabled = !openableSingle;
   elements.editButton.classList.toggle("hidden", isMulti || items.length !== 1 || items[0].kind !== "file");
   elements.editButton.disabled = !editableSingle;
   elements.renameButton.classList.toggle("hidden", isMulti);