diff --git a/lib/components/shared/dialogs/prompt_dialog.dart b/lib/components/shared/dialogs/prompt_dialog.dart
new file mode 100644
index 000000000..1bc4af920
--- /dev/null
+++ b/lib/components/shared/dialogs/prompt_dialog.dart
@@ -0,0 +1,49 @@
+import 'package:flutter/cupertino.dart';
+import 'package:platform_ui/platform_ui.dart';
+import 'package:spotube/components/root/sidebar.dart';
+
+Future<bool> showPromptDialog({
+  required BuildContext context,
+  required String title,
+  required String message,
+  String okText = "Ok",
+  String cancelText = "Cancel",
+}) async {
+  return showPlatformAlertDialog<bool>(
+    context,
+    builder: (context) {
+      return PlatformAlertDialog(
+        title: PlatformText(title),
+        content: PlatformText(message),
+        macosAppIcon: Sidebar.brandLogo(),
+        primaryActions: [
+          if (platform == TargetPlatform.iOS)
+            CupertinoDialogAction(
+              isDefaultAction: true,
+              child: PlatformText(okText),
+              onPressed: () => Navigator.of(context).pop(true),
+            )
+          else
+            PlatformFilledButton(
+              child: PlatformText(okText),
+              onPressed: () => Navigator.of(context).pop(true),
+            ),
+        ],
+        secondaryActions: [
+          if (platform == TargetPlatform.iOS)
+            CupertinoDialogAction(
+              isDefaultAction: false,
+              child: PlatformText(cancelText),
+              onPressed: () => Navigator.of(context).pop(false),
+            )
+          else
+            PlatformFilledButton(
+              isSecondary: true,
+              onPressed: () => Navigator.of(context).pop(false),
+              child: PlatformText(cancelText),
+            ),
+        ],
+      );
+    },
+  ).then((value) => value ?? false);
+}
diff --git a/lib/pages/search/search.dart b/lib/pages/search/search.dart
index 8e046f569..b2d38c08b 100644
--- a/lib/pages/search/search.dart
+++ b/lib/pages/search/search.dart
@@ -7,6 +7,7 @@ import 'package:platform_ui/platform_ui.dart';
 import 'package:spotify/spotify.dart';
 import 'package:spotube/collections/spotube_icons.dart';
 import 'package:spotube/components/album/album_card.dart';
+import 'package:spotube/components/shared/dialogs/prompt_dialog.dart';
 import 'package:spotube/components/shared/shimmers/shimmer_playbutton_card.dart';
 import 'package:spotube/components/shared/fallbacks/anonymous_fallback.dart';
 import 'package:spotube/components/shared/page_window_title_bar.dart';
@@ -171,11 +172,28 @@ class SearchPage extends HookConsumerWidget {
                                       onTrackPlayButtonPressed:
                                           (currentTrack) async {
                                         final isTrackPlaying =
-                                            playlist?.activeTrack.id !=
+                                            playlist?.activeTrack.id ==
                                                 currentTrack.id;
-                                        if (!isTrackPlaying) {
-                                          await playlistNotifier
-                                              .loadAndPlay([currentTrack]);
+                                        if (!isTrackPlaying &&
+                                            context.mounted) {
+                                          final shouldPlay =
+                                              (playlist?.tracks.length ?? 0) >
+                                                      20
+                                                  ? await showPromptDialog(
+                                                      context: context,
+                                                      title:
+                                                          "Playing ${currentTrack.name}",
+                                                      message:
+                                                          "This will clear the current queue. "
+                                                          "${playlist?.tracks.length ?? 0} tracks will be removed\n"
+                                                          "Do you want to continue?",
+                                                    )
+                                                  : true;
+
+                                          if (shouldPlay) {
+                                            await playlistNotifier
+                                                .loadAndPlay([currentTrack]);
+                                          }
                                         }
                                       },
                                     );