diff --git a/pkgs/cli_util/CHANGELOG.md b/pkgs/cli_util/CHANGELOG.md
index 4355f64fd9..22d7619946 100644
--- a/pkgs/cli_util/CHANGELOG.md
+++ b/pkgs/cli_util/CHANGELOG.md
@@ -1,3 +1,7 @@
+## 0.5.2
+
+- Add a legend to multiselect dialogs to make the usage more obvious.
+
 ## 0.5.1
 
 - Add `showMultiSelectDialog` and `showSingleSelectDialog` to new
diff --git a/pkgs/cli_util/lib/src/components/select_dialog.dart b/pkgs/cli_util/lib/src/components/select_dialog.dart
index b7c14206de..95d60e9d22 100644
--- a/pkgs/cli_util/lib/src/components/select_dialog.dart
+++ b/pkgs/cli_util/lib/src/components/select_dialog.dart
@@ -9,6 +9,8 @@ import 'dart:async';
 import 'dart:io';
 import 'dart:math' as math;
 
+import 'package:meta/meta.dart';
+
 import 'keys.dart';
 
 /// Shows a scrollable terminal selection dialog and returns the set of
@@ -142,12 +144,13 @@ Future<Set<int>?> _runDialog(
   final cleanupTasks = <FutureOr<void> Function()>[
     () {
       // Try to clear the dialog from the terminal
-      final visibleCount = math.min(options.length, maxVisibleItems);
-      stdout.write('\x1b[${visibleCount}A'); // Move cursor to top
-      for (var i = 0; i < visibleCount; i++) {
+      var linesToClear = math.min(options.length, maxVisibleItems);
+      if (multiSelect) linesToClear++;
+      stdout.write('\x1b[${linesToClear}A'); // Move cursor to top
+      for (var i = 0; i < linesToClear; i++) {
         stdout.write('\x1b[2K\n'); // Clear each line
       }
-      stdout.write('\x1b[${visibleCount}A'); // Move back
+      stdout.write('\x1b[${linesToClear}A'); // Move back
     },
   ];
   try {
@@ -317,7 +320,8 @@ void _render({
 
   // Move the cursor to the top of the dialog if we're not on the first render.
   if (!isFirstRender) {
-    stdout.write('\x1b[${visibleCount}A');
+    final linesToMoveUp = multiSelect ? visibleCount + 1 : visibleCount;
+    stdout.write('\x1b[${linesToMoveUp}A');
   }
 
   var thumbHeight = 0;
@@ -383,6 +387,21 @@ void _render({
       stdout.write('$line\n');
     }
   }
+
+  if (multiSelect) {
+    stdout.write('\x1b[2m$multiSelectLegend\x1b[0m\n');
+  }
+}
+
+/// The legend text displayed at the bottom of multi-select dialogs, trimmed
+/// to the terminal width.
+@visibleForTesting
+String get multiSelectLegend {
+  const fullText =
+      'Toggle: Space | Toggle All: Ctrl+A | Submit: Enter | Abort: Esc';
+  final width = _terminalWidth;
+  final limit = math.max(0, width - 1);
+  return fullText.length > limit ? fullText.substring(0, limit) : fullText;
 }
 
 /// Returns the minimum width required to display a dialog with the given
diff --git a/pkgs/cli_util/pubspec.yaml b/pkgs/cli_util/pubspec.yaml
index 6367dafd5e..f3979b6365 100644
--- a/pkgs/cli_util/pubspec.yaml
+++ b/pkgs/cli_util/pubspec.yaml
@@ -1,5 +1,5 @@
 name: cli_util
-version: 0.5.1
+version: 0.5.2
 description: A library to help in building Dart command-line apps.
 repository: https://github.com/dart-lang/tools/tree/main/pkgs/cli_util
 issue_tracker: https://github.com/dart-lang/tools/issues?q=is%3Aissue+is%3Aopen+label%3Apackage%3Acli_util
diff --git a/pkgs/cli_util/test/fake_terminal.dart b/pkgs/cli_util/test/fake_terminal.dart
index 6463e66251..002d53c1f4 100644
--- a/pkgs/cli_util/test/fake_terminal.dart
+++ b/pkgs/cli_util/test/fake_terminal.dart
@@ -25,7 +25,7 @@ class FakeTerminal {
   void write(String text) {
     // Regex for the specific escape sequences used in select_dialog.dart
     final seqRegex = RegExp(
-      r'(\x1b\[\d*A|\x1b\[2K|\x1b\[1m|\x1b\[0m|\x1b\[\?25[lh])',
+      r'(\x1b\[\d*A|\x1b\[2K|\x1b\[1m|\x1b\[2m|\x1b\[0m|\x1b\[\?25[lh])',
     );
 
     var lastEnd = 0;
diff --git a/pkgs/cli_util/test/select_dialog_test.dart b/pkgs/cli_util/test/select_dialog_test.dart
index a21a85c369..cb3fca6341 100644
--- a/pkgs/cli_util/test/select_dialog_test.dart
+++ b/pkgs/cli_util/test/select_dialog_test.dart
@@ -251,6 +251,10 @@ void main() {
           final renderer =
               multiSelect ? showMultiSelectDialog : showSingleSelectDialog;
 
+          // Always compute this on demand to account for the current terminal
+          // width.
+          String maybeLegend() => multiSelect ? '$multiSelectLegend\n' : '';
+
           test('renders UI state correctly', () async {
             final future = renderer([
               'apple',
@@ -262,7 +266,7 @@ void main() {
 >$uBox apple
  $uBox banana
  $uBox cherry
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.down);
             await pumpEventQueue();
@@ -270,7 +274,7 @@ void main() {
  $uBox apple
 >$uBox banana
  $uBox cherry
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.space);
             await pumpEventQueue();
@@ -278,7 +282,7 @@ void main() {
  $uBox apple
 >$sBox banana
  $uBox cherry
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.enter);
             expect(await future, multiSelect ? {1} : 1);
@@ -298,7 +302,7 @@ void main() {
  $uBox c      █
  $uBox d      █
  $uBox e      │
-''');
+${maybeLegend()}''');
             inputController.addKeys(List.filled(2, KeyVariants.down));
             inputController.addKey(KeyVariants.space);
             await pumpEventQueue();
@@ -309,7 +313,7 @@ void main() {
 >$sBox c      █
  $uBox d      █
  $uBox e      │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(4, KeyVariants.down));
             await pumpEventQueue();
@@ -320,7 +324,7 @@ void main() {
  $uBox e      █
  $uBox f      █
 >$uBox g      █
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.enter);
             expect(await future, multiSelect ? {2} : 6);
@@ -341,7 +345,7 @@ void main() {
  $uBox 2       │
  $uBox 3       │
  $uBox 4       │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(2, KeyVariants.down));
             await pumpEventQueue();
@@ -351,7 +355,7 @@ void main() {
 >$uBox 2       │
  $uBox 3       │
  $uBox 4       │
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.down);
             await pumpEventQueue();
@@ -361,7 +365,7 @@ void main() {
 >$uBox 3       │
  $uBox 4       │
  $uBox 5       │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(6, KeyVariants.down));
             await pumpEventQueue();
@@ -371,7 +375,7 @@ void main() {
 >$uBox 9       │
  $uBox 10      │
  $uBox 11      │
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.down);
             await pumpEventQueue();
@@ -381,7 +385,7 @@ void main() {
 >$uBox 10      █
  $uBox 11      │
  $uBox 12      │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(5, KeyVariants.down));
             await pumpEventQueue();
@@ -391,7 +395,7 @@ void main() {
 >$uBox 15      █
  $uBox 16      │
  $uBox 17      │
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.down);
             await pumpEventQueue();
@@ -401,7 +405,7 @@ void main() {
 >$uBox 16      │
  $uBox 17      █
  $uBox 18      │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(5, KeyVariants.down));
             await pumpEventQueue();
@@ -411,7 +415,7 @@ void main() {
 >$uBox 21      │
  $uBox 22      █
  $uBox 23      │
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.down);
             await pumpEventQueue();
@@ -421,7 +425,7 @@ void main() {
 >$uBox 22      │
  $uBox 23      │
  $uBox 24      █
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(2, KeyVariants.down));
             await pumpEventQueue();
@@ -431,7 +435,7 @@ void main() {
  $uBox 22      │
  $uBox 23      │
 >$uBox 24      █
-''');
+${maybeLegend()}''');
 
             inputController.addKeys([KeyVariants.space, KeyVariants.enter]);
             expect(await future, multiSelect ? {24} : 24);
@@ -452,7 +456,7 @@ void main() {
  $uBox 2      █
  $uBox 3      █
  $uBox 4      │
-''');
+${maybeLegend()}''');
 
             inputController.addKeys(List.filled(4, KeyVariants.down));
             await pumpEventQueue();
@@ -463,7 +467,7 @@ void main() {
  $uBox 3      █
 >$uBox 4      █
  $uBox 5      █
-''');
+${maybeLegend()}''');
 
             inputController.addKey(KeyVariants.enter);
             expect(await future, multiSelect ? <int>{} : 4);
@@ -480,7 +484,7 @@ void main() {
             expect(mockStdout.terminal.content, '''
 >$uBox abcdefg
  $uBox hijklmn
-''');
+${maybeLegend()}''');
 
             inputController.addKeys([KeyVariants.space, KeyVariants.enter]);
             expect(await future, multiSelect ? <int>{0} : 0);
@@ -497,7 +501,7 @@ void main() {
             expect(mockStdout.terminal.content, '''
 >$uBox abcdefg
  $uBox hijk...
-''');
+${maybeLegend()}''');
 
             inputController.addKeys([KeyVariants.space, KeyVariants.enter]);
             expect(await future, multiSelect ? <int>{0} : 0);
@@ -514,7 +518,7 @@ void main() {
             expect(mockStdout.terminal.content, '''
 >$uBox a very long opt...
  $uBox short
-''');
+${maybeLegend()}''');
 
             inputController.addKeys([KeyVariants.space, KeyVariants.enter]);
             expect(await future, multiSelect ? {0} : 0);
@@ -538,7 +542,7 @@ void main() {
  $uBox c                █
  $uBox d                █
  $uBox e                │
-''');
+${maybeLegend()}''');
 
             if (multiSelect) {
               inputController.addKeys([KeyVariants.space, KeyVariants.enter]);
@@ -561,6 +565,7 @@ void main() {
 > [ ] apple
   [x] banana
   [x] cherry
+$multiSelectLegend
 ''');
           inputController.addKey(KeyVariants.enter);
           expect(await future, {1, 2});
@@ -577,6 +582,7 @@ void main() {
 > [ ] apple
   [ ] banana
   [ ] cherry
+$multiSelectLegend
 ''');
 
           inputController.addKey(KeyVariants.selectAll);
@@ -585,6 +591,7 @@ void main() {
 > [x] apple
   [x] banana
   [x] cherry
+$multiSelectLegend
 ''');
 
           inputController.addKey(KeyVariants.selectAll);
@@ -593,6 +600,7 @@ void main() {
 > [ ] apple
   [ ] banana
   [ ] cherry
+$multiSelectLegend
 ''');
 
           inputController.addKey(KeyVariants.enter);