diff --git a/app/src/main/java/com/cappielloantonio/tempo/ui/dialog/PlaylistChooserDialog.java b/app/src/main/java/com/cappielloantonio/tempo/ui/dialog/PlaylistChooserDialog.java
index 360a5ec5..7337e930 100644
--- a/app/src/main/java/com/cappielloantonio/tempo/ui/dialog/PlaylistChooserDialog.java
+++ b/app/src/main/java/com/cappielloantonio/tempo/ui/dialog/PlaylistChooserDialog.java
@@ -27,6 +27,8 @@ public class PlaylistChooserDialog extends DialogFragment implements ClickCallba
 
     private PlaylistDialogHorizontalAdapter playlistDialogHorizontalAdapter;
 
+    private boolean SkipDuplicates;
+
     @NonNull
     @Override
     public Dialog onCreateDialog(Bundle savedInstanceState) {
@@ -78,10 +80,15 @@ public class PlaylistChooserDialog extends DialogFragment implements ClickCallba
     private void initPlaylistView() {
         bind.playlistDialogRecyclerView.setLayoutManager(new LinearLayoutManager(requireContext()));
         bind.playlistDialogRecyclerView.setHasFixedSize(true);
+        SkipDuplicates = true;
 
         playlistDialogHorizontalAdapter = new PlaylistDialogHorizontalAdapter(this);
         bind.playlistDialogRecyclerView.setAdapter(playlistDialogHorizontalAdapter);
 
+        bind.playlistChooserDialogSkipDuplicates.setOnCheckedChangeListener((__, isChecked) -> {
+            SkipDuplicates = isChecked;
+        });
+
         playlistChooserViewModel.getPlaylistList(requireActivity()).observe(requireActivity(), playlists -> {
             if (playlists != null) {
                 if (!playlists.isEmpty()) {
@@ -100,8 +107,7 @@ public class PlaylistChooserDialog extends DialogFragment implements ClickCallba
     public void onPlaylistClick(Bundle bundle) {
         if (playlistChooserViewModel.getSongsToAdd() != null && !playlistChooserViewModel.getSongsToAdd().isEmpty()) {
             Playlist playlist = bundle.getParcelable(Constants.PLAYLIST_OBJECT);
-            playlistChooserViewModel.addSongsToPlaylist(playlist.getId());
-            dismiss();
+            playlistChooserViewModel.addSongsToPlaylist(this, getDialog(), playlist.getId(), SkipDuplicates);
         } else {
             Toast.makeText(requireContext(), R.string.playlist_chooser_dialog_toast_add_failure, Toast.LENGTH_SHORT).show();
         }
diff --git a/app/src/main/java/com/cappielloantonio/tempo/viewmodel/PlaylistChooserViewModel.java b/app/src/main/java/com/cappielloantonio/tempo/viewmodel/PlaylistChooserViewModel.java
index 2ec6c21f..82e0418b 100644
--- a/app/src/main/java/com/cappielloantonio/tempo/viewmodel/PlaylistChooserViewModel.java
+++ b/app/src/main/java/com/cappielloantonio/tempo/viewmodel/PlaylistChooserViewModel.java
@@ -1,6 +1,7 @@
 package com.cappielloantonio.tempo.viewmodel;
 
 import android.app.Application;
+import android.app.Dialog;
 
 import androidx.annotation.NonNull;
 import androidx.lifecycle.AndroidViewModel;
@@ -14,7 +15,6 @@ import com.cappielloantonio.tempo.subsonic.models.Playlist;
 import com.google.common.collect.Lists;
 
 import java.util.ArrayList;
-import java.util.Collections;
 import java.util.List;
 
 public class PlaylistChooserViewModel extends AndroidViewModel {
@@ -34,8 +34,19 @@ public class PlaylistChooserViewModel extends AndroidViewModel {
         return playlists;
     }
 
-    public void addSongsToPlaylist(String playlistId) {
-        playlistRepository.addSongToPlaylist(playlistId, new ArrayList<>(Lists.transform(toAdd, Child::getId)));
+    public void addSongsToPlaylist(LifecycleOwner owner, Dialog dialog, String playlistId, boolean skipDuplicates) {
+        List<String> songIds = Lists.transform(toAdd, Child::getId);
+        if (skipDuplicates) {
+            playlistRepository.getPlaylistSongs(playlistId).observe(owner, playlistSongs -> {
+                List<String> playlistSongIds = Lists.transform(playlistSongs, Child::getId);
+                songIds.removeAll(playlistSongIds);
+                playlistRepository.addSongToPlaylist(playlistId, new ArrayList<>(songIds));
+                dialog.dismiss();
+            });
+        } else {
+            playlistRepository.addSongToPlaylist(playlistId, new ArrayList<>(songIds));
+            dialog.dismiss();
+        }
     }
 
     public void setSongsToAdd(ArrayList<Child> songs) {
diff --git a/app/src/main/res/layout/dialog_playlist_chooser.xml b/app/src/main/res/layout/dialog_playlist_chooser.xml
index 80b4bfbe..1c7690e4 100644
--- a/app/src/main/res/layout/dialog_playlist_chooser.xml
+++ b/app/src/main/res/layout/dialog_playlist_chooser.xml
@@ -19,7 +19,15 @@
     <androidx.recyclerview.widget.RecyclerView
         android:id="@+id/playlist_dialog_recycler_view"
         android:layout_width="match_parent"
-        android:layout_height="wrap_content"
+        android:layout_height="0dp"
+        android:layout_weight="1"
         android:layout_marginTop="8dp"
         android:clipToPadding="false" />
+
+    <CheckBox
+        android:id="@+id/playlist_chooser_dialog_skip_duplicates"
+        android:layout_width="match_parent"
+        android:layout_height="wrap_content"
+        android:text="@string/playlist_chooser_dialog_skip_duplicates"
+        android:checked="true" />
 </LinearLayout>
\ No newline at end of file
diff --git a/app/src/main/res/values/strings.xml b/app/src/main/res/values/strings.xml
index 619766d5..fbdcff4b 100644
--- a/app/src/main/res/values/strings.xml
+++ b/app/src/main/res/values/strings.xml
@@ -207,6 +207,7 @@
     <string name="playlist_chooser_dialog_negative_button">Cancel</string>
     <string name="playlist_chooser_dialog_neutral_button">Create</string>
     <string name="playlist_chooser_dialog_title">Add to a playlist</string>
+    <string name="playlist_chooser_dialog_skip_duplicates">Skip duplicates</string>
     <string name="playlist_chooser_dialog_toast_add_success">Added song to playlist</string>
     <string name="playlist_chooser_dialog_toast_add_failure">Failed to add song to playlist</string>
     <string name="playlist_counted_tracks">%1$d tracks •  %2$s</string>