diff --git a/webui/backend/data/tasks.db b/webui/backend/data/tasks.db
index 8df5d3f..2924554 100644
Binary files a/webui/backend/data/tasks.db and b/webui/backend/data/tasks.db differ
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 d4d5be5..85b4696 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 51ba908..3380c41 100644
--- a/webui/backend/tests/golden/test_ui_smoke_golden.py
+++ b/webui/backend/tests/golden/test_ui_smoke_golden.py
@@ -274,7 +274,10 @@ class UiSmokeGoldenTest(unittest.TestCase):
         self.assertIn("function mediaIconSvg(type)", app_js)
         self.assertIn('const iconType = iconTypeForEntry(entry);', app_js)
         self.assertIn('function createMediaSlot(entry)', app_js)
-        self.assertNotIn("select-marker", app_js)
+        self.assertIn('function createSelectionSlot(pane, entry, index)', app_js)
+        self.assertIn('entry-select-slot', app_js)
+        self.assertIn('entry-select-toggle', app_js)
+        self.assertIn('toggleSelectionAtIndex(pane, selectedEntryFromItem(entry), index);', app_js)
         self.assertIn('function openSearch()', app_js)
         self.assertIn('async function submitSearch()', app_js)
         self.assertIn('async function openInfo()', app_js)
diff --git a/webui/html/app.js b/webui/html/app.js
index c6cb557..17d701d 100644
--- a/webui/html/app.js
+++ b/webui/html/app.js
@@ -1237,6 +1237,45 @@ function createMediaSlot(entry) {
   return slot;
 }
 
+function createSelectionSlot(pane, entry, index) {
+  const slot = document.createElement("span");
+  slot.className = "entry-select-slot";
+
+  if (entry.isParent) {
+    const placeholder = document.createElement("span");
+    placeholder.className = "entry-select-toggle is-disabled";
+    placeholder.setAttribute("aria-hidden", "true");
+    const indicator = document.createElement("span");
+    indicator.className = "entry-select-indicator";
+    placeholder.append(indicator);
+    slot.append(placeholder);
+    return slot;
+  }
+
+  const button = document.createElement("button");
+  button.type = "button";
+  button.className = "entry-select-toggle";
+  const selected = selectedPaths(pane).includes(entry.path);
+  if (selected) {
+    button.classList.add("is-selected");
+  }
+  button.setAttribute("aria-label", `${selected ? "Deselect" : "Select"} ${entry.name}`);
+  button.setAttribute("aria-pressed", selected ? "true" : "false");
+  const indicator = document.createElement("span");
+  indicator.className = "entry-select-indicator";
+  button.append(indicator);
+  button.onclick = (event) => {
+    event.preventDefault();
+    event.stopPropagation();
+    setActivePane(pane);
+    paneState(pane).currentRowIndex = index;
+    toggleSelectionAtIndex(pane, selectedEntryFromItem(entry), index);
+    renderPaneItems(pane);
+  };
+  slot.append(button);
+  return slot;
+}
+
 async function loadSettings() {
   const data = await apiRequest("GET", "/api/settings");
   settingsState.showThumbnails = !!data.show_thumbnails;
@@ -1546,7 +1585,7 @@ function formatFileSize(bytes) {
   return `${(bytes / (1024 ** 4)).toFixed(1)} TB`;
 }
 
-function createBrowseItem(pane, entry, kind) {
+function createBrowseItem(pane, entry, kind, index) {
   const li = document.createElement("li");
   li.className = "selectable";
   li.dataset.path = entry.path;
@@ -1567,6 +1606,7 @@ function createBrowseItem(pane, entry, kind) {
 
   const name = document.createElement("span");
   name.className = `entry-name ${kind === "directory" ? "entry-dir" : "entry-file"}`;
+  name.append(createSelectionSlot(pane, { ...entry, kind }, index));
   name.append(createMediaSlot({ ...entry, kind }));
 
   if (kind === "directory") {
@@ -1680,6 +1720,7 @@ function renderPaneItems(pane) {
       };
       const upNameCell = document.createElement("span");
       upNameCell.className = "entry-name entry-dir";
+      upNameCell.append(createSelectionSlot(pane, { ...entry, isParent: true }, index));
       upNameCell.append(createMediaSlot({ name: "..", path: entry.path, kind: "directory" }));
       const upName = document.createElement("button");
       upName.type = "button";
@@ -1705,7 +1746,7 @@ function renderPaneItems(pane) {
       return;
     }
 
-    const row = createBrowseItem(pane, entry, entry.kind);
+    const row = createBrowseItem(pane, entry, entry.kind, index);
     row.dataset.rowIndex = String(index);
     if (index === model.currentRowIndex) {
       row.classList.add("is-current-row");
@@ -1724,7 +1765,7 @@ function renderPaneItems(pane) {
         navigateTo(pane, entry.path);
       };
     }
-    const fileName = row.querySelector(".entry-file span");
+    const fileName = row.querySelector(".entry-file .entry-label");
     if (fileName) {
       fileName.onclick = (ev) => {
         ev.stopPropagation();
diff --git a/webui/html/base.css b/webui/html/base.css
index cfee420..60dce9a 100644
--- a/webui/html/base.css
+++ b/webui/html/base.css
@@ -346,6 +346,72 @@ button:disabled {
   min-width: 0;
 }
 
+.entry-select-slot {
+  width: 18px;
+  min-width: 18px;
+  height: 18px;
+  display: inline-flex;
+  align-items: center;
+  justify-content: center;
+}
+
+.entry-select-toggle {
+  width: 18px;
+  min-width: 18px;
+  height: 18px;
+  padding: 0;
+  border: none;
+  border-radius: 999px;
+  background: transparent;
+  display: inline-flex;
+  align-items: center;
+  justify-content: center;
+  box-shadow: none;
+}
+
+.entry-select-toggle:hover {
+  background: transparent;
+  border-color: transparent;
+  box-shadow: none;
+}
+
+.entry-select-toggle.is-disabled {
+  pointer-events: none;
+}
+
+.entry-select-indicator {
+  width: 16px;
+  height: 16px;
+  border-radius: 999px;
+  border: 1.5px solid color-mix(in srgb, var(--color-text-muted) 80%, transparent);
+  opacity: 0;
+  transition: opacity 100ms ease, border-color 100ms ease, background 100ms ease;
+  position: relative;
+}
+
+.list li:hover .entry-select-indicator,
+.entry-select-toggle:focus-visible .entry-select-indicator,
+.entry-select-toggle.is-selected .entry-select-indicator {
+  opacity: 1;
+}
+
+.entry-select-toggle.is-selected .entry-select-indicator {
+  border-color: var(--color-accent);
+  background: var(--color-accent);
+}
+
+.entry-select-toggle.is-selected .entry-select-indicator::after {
+  content: "✓";
+  position: absolute;
+  inset: 0;
+  display: flex;
+  align-items: center;
+  justify-content: center;
+  font-size: 11px;
+  line-height: 1;
+  color: var(--color-surface);
+}
+
 .entry-media-slot {
   width: 28px;
   min-width: 28px;