diff --git a/app/src/main/java/de/danoeh/antennapod/fragment/QueueFragment.java b/app/src/main/java/de/danoeh/antennapod/fragment/QueueFragment.java
index 4947d5a87..4b926200d 100644
--- a/app/src/main/java/de/danoeh/antennapod/fragment/QueueFragment.java
+++ b/app/src/main/java/de/danoeh/antennapod/fragment/QueueFragment.java
@@ -276,12 +276,22 @@ public class QueueFragment extends Fragment {
 
             MenuItemUtils.refreshLockItem(getActivity(), menu);
 
-            // Show Lock Item and Sort Item only if queue is sorted manually
-            boolean sortedManually = UserPreferences.isQueueSortedManually();
+            // Show Lock Item only if queue is sorted manually
+            boolean sortedAutomatically = UserPreferences.isQueueSortedAutomatically();
             MenuItem lockItem = menu.findItem(R.id.queue_lock);
-            lockItem.setVisible(sortedManually);
-            MenuItem sortItem = menu.findItem(R.id.queue_sort);
-            sortItem.setVisible(sortedManually);
+            lockItem.setVisible(!sortedAutomatically);
+
+            // Set keep sorted checkbox
+            MenuItem sortedAutomaticallyItem = menu.findItem(R.id.queue_sort_automatically);
+            sortedAutomaticallyItem.setChecked(sortedAutomatically);
+
+            // Hide sort menu items for sort orders that are not supported by automatic sort.
+            MenuItem sortRandomItem = menu.findItem(R.id.queue_sort_random);
+            sortRandomItem.setVisible(!sortedAutomatically);
+            MenuItem sortSmart1Item = menu.findItem(R.id.queue_sort_smart_shuffle_asc);
+            sortSmart1Item.setVisible(!sortedAutomatically);
+            MenuItem sortSmart2Item = menu.findItem(R.id.queue_sort_smart_shuffle_desc);
+            sortSmart2Item.setVisible(!sortedAutomatically);
 
             isUpdatingFeeds = MenuItemUtils.updateRefreshMenuItem(menu, R.id.refresh_item, updateRefreshMenuItemChecker);
         }
@@ -331,38 +341,52 @@ public class QueueFragment extends Fragment {
                     ((MainActivity) requireActivity()) .loadChildFragment(
                             EpisodesApplyActionFragment.newInstance(queue, ACTION_DELETE | ACTION_REMOVE_FROM_QUEUE));
                     return true;
+                case R.id.queue_sort_automatically:
+                    boolean sortedAutomaticallyOld = UserPreferences.isQueueSortedAutomatically();
+                    boolean sortedAutomaticallyNew = !sortedAutomaticallyOld;
+                    if (sortedAutomaticallyNew) {
+                        // We have to choose an initially sort order, let's sort by episode date
+                        UserPreferences.QueueSortOrder sortOrder = UserPreferences.QueueSortOrder.DATE_NEW_OLD;
+                        UserPreferences.setQueueSortOrder(sortOrder);
+                        QueueSorter.sort(QueueSorter.queueSortOrder2Rule(sortOrder), true);
+                    } else {
+                        UserPreferences.setQueueSortOrder(UserPreferences.QueueSortOrder.MANUALLY);
+                    }
+                    // Update sort menu items visibility and state
+                    getActivity().invalidateOptionsMenu();
+                    return true;
                 case R.id.queue_sort_episode_title_asc:
-                    QueueSorter.sort(QueueSorter.Rule.EPISODE_TITLE_ASC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.EPISODE_TITLE_ASC);
                     return true;
                 case R.id.queue_sort_episode_title_desc:
-                    QueueSorter.sort(QueueSorter.Rule.EPISODE_TITLE_DESC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.EPISODE_TITLE_DESC);
                     return true;
                 case R.id.queue_sort_date_asc:
-                    QueueSorter.sort(QueueSorter.Rule.DATE_ASC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.DATE_ASC);
                     return true;
                 case R.id.queue_sort_date_desc:
-                    QueueSorter.sort(QueueSorter.Rule.DATE_DESC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.DATE_DESC);
                     return true;
                 case R.id.queue_sort_duration_asc:
-                    QueueSorter.sort(QueueSorter.Rule.DURATION_ASC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.DURATION_ASC);
                     return true;
                 case R.id.queue_sort_duration_desc:
-                    QueueSorter.sort(QueueSorter.Rule.DURATION_DESC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.DURATION_DESC);
                     return true;
                 case R.id.queue_sort_feed_title_asc:
-                    QueueSorter.sort(QueueSorter.Rule.FEED_TITLE_ASC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.FEED_TITLE_ASC);
                     return true;
                 case R.id.queue_sort_feed_title_desc:
-                    QueueSorter.sort(QueueSorter.Rule.FEED_TITLE_DESC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.FEED_TITLE_DESC);
                     return true;
                 case R.id.queue_sort_random:
-                    QueueSorter.sort(QueueSorter.Rule.RANDOM, true);
+                    queueSortOrderChanged(QueueSorter.Rule.RANDOM);
                     return true;
                 case R.id.queue_sort_smart_shuffle_asc:
-                    QueueSorter.sort(QueueSorter.Rule.SMART_SHUFFLE_ASC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.SMART_SHUFFLE_ASC);
                     return true;
                 case R.id.queue_sort_smart_shuffle_desc:
-                    QueueSorter.sort(QueueSorter.Rule.SMART_SHUFFLE_DESC, true);
+                    queueSortOrderChanged(QueueSorter.Rule.SMART_SHUFFLE_DESC);
                     return true;
                 default:
                     return false;
@@ -372,6 +396,22 @@ public class QueueFragment extends Fragment {
         }
     }
 
+    /**
+     * Sorts the queue on user interaction.
+     * If the queue is sorted automatically, the new sort order is stored in the preferences.
+     *
+     * @param rule Sort rule.
+     */
+    private void queueSortOrderChanged(QueueSorter.Rule rule) {
+        boolean sortedAutomatically = UserPreferences.isQueueSortedAutomatically();
+        UserPreferences.QueueSortOrder sortOrder = QueueSorter.rule2QueueSortOrder(rule);
+        // remember sort order to keep queue sorted
+        if (sortedAutomatically && sortOrder != null) {
+            UserPreferences.setQueueSortOrder(sortOrder);
+        }
+        // Sort queue
+        QueueSorter.sort(rule, true);
+    }
 
     @Override
     public boolean onContextItemSelected(MenuItem item) {
diff --git a/app/src/main/java/de/danoeh/antennapod/fragment/preferences/UserInterfacePreferencesFragment.java b/app/src/main/java/de/danoeh/antennapod/fragment/preferences/UserInterfacePreferencesFragment.java
index db852cee7..8c0e0295f 100644
--- a/app/src/main/java/de/danoeh/antennapod/fragment/preferences/UserInterfacePreferencesFragment.java
+++ b/app/src/main/java/de/danoeh/antennapod/fragment/preferences/UserInterfacePreferencesFragment.java
@@ -11,11 +11,7 @@ import android.widget.ListView;
 import android.widget.Toast;
 import de.danoeh.antennapod.R;
 import de.danoeh.antennapod.activity.MainActivity;
-import de.danoeh.antennapod.core.feed.FeedItem;
 import de.danoeh.antennapod.core.preferences.UserPreferences;
-import de.danoeh.antennapod.core.storage.DBWriter;
-import de.danoeh.antennapod.core.util.Permutor;
-import de.danoeh.antennapod.core.util.QueueSorter;
 
 import org.apache.commons.lang3.ArrayUtils;
 
@@ -94,17 +90,6 @@ public class UserInterfacePreferencesFragment extends PreferenceFragmentCompat {
         if (Build.VERSION.SDK_INT >= 26) {
             findPreference(UserPreferences.PREF_EXPANDED_NOTIFICATION).setVisible(false);
         }
-
-        findPreference(UserPreferences.PREF_QUEUE_SORT_ORDER)
-                .setOnPreferenceChangeListener((preference, newValue) -> {
-                    UserPreferences.QueueSortOrder newSortOrder = UserPreferences.parseQueueSortOrder((String) newValue);
-                    if (newSortOrder != UserPreferences.QueueSortOrder.MANUALLY) {
-                        QueueSorter.Rule sortRule = QueueSorter.queueSortOrder2Rule(newSortOrder);
-                        Permutor<FeedItem> permutor = QueueSorter.getPermutor(sortRule);
-                        DBWriter.reorderQueue(permutor, true);
-                    }
-                    return true;
-                });
     }
 
     private void showDrawerPreferencesDialog() {
diff --git a/app/src/main/java/de/danoeh/antennapod/menuhandler/FeedItemMenuHandler.java b/app/src/main/java/de/danoeh/antennapod/menuhandler/FeedItemMenuHandler.java
index 0c7622a47..5d6af35da 100644
--- a/app/src/main/java/de/danoeh/antennapod/menuhandler/FeedItemMenuHandler.java
+++ b/app/src/main/java/de/danoeh/antennapod/menuhandler/FeedItemMenuHandler.java
@@ -15,7 +15,6 @@ import de.danoeh.antennapod.core.gpoddernet.model.GpodnetEpisodeAction.Action;
 import de.danoeh.antennapod.core.preferences.GpodnetPreferences;
 import de.danoeh.antennapod.core.preferences.UserPreferences;
 import de.danoeh.antennapod.core.service.playback.PlaybackService;
-import de.danoeh.antennapod.core.storage.DBTasks;
 import de.danoeh.antennapod.core.storage.DBWriter;
 import de.danoeh.antennapod.core.util.FeedItemUtil;
 import de.danoeh.antennapod.core.util.IntentUtils;
@@ -68,17 +67,17 @@ public class FeedItemMenuHandler {
         }
         boolean hasMedia = selectedItem.getMedia() != null;
         boolean isPlaying = hasMedia && selectedItem.getState() == FeedItem.State.PLAYING;
-        boolean sortedManually = UserPreferences.isQueueSortedManually();
+        boolean sortedAutomatically = UserPreferences.isQueueSortedAutomatically();
 
         if (!isPlaying) {
             mi.setItemVisibility(R.id.skip_episode_item, false);
         }
 
         boolean isInQueue = selectedItem.isTagged(FeedItem.TAG_QUEUE);
-        if (queueAccess == null || queueAccess.size() == 0 || queueAccess.get(0) == selectedItem.getId() || !sortedManually) {
+        if (queueAccess == null || queueAccess.size() == 0 || queueAccess.get(0) == selectedItem.getId() || sortedAutomatically) {
             mi.setItemVisibility(R.id.move_to_top_item, false);
         }
-        if (queueAccess == null || queueAccess.size() == 0 || queueAccess.get(queueAccess.size()-1) == selectedItem.getId() || !sortedManually) {
+        if (queueAccess == null || queueAccess.size() == 0 || queueAccess.get(queueAccess.size()-1) == selectedItem.getId() || sortedAutomatically) {
             mi.setItemVisibility(R.id.move_to_bottom_item, false);
         }
         if (!isInQueue) {
diff --git a/app/src/main/res/menu/queue.xml b/app/src/main/res/menu/queue.xml
index 0f7729be1..99f0fd950 100644
--- a/app/src/main/res/menu/queue.xml
+++ b/app/src/main/res/menu/queue.xml
@@ -28,6 +28,11 @@
         android:title="@string/sort">
 
         <menu>
+            <item
+                android:id="@+id/queue_sort_automatically"
+                android:title="@string/sort_automatically"
+                android:checkable="true" />
+
             <item
                 android:id="@+id/queue_sort_date"
                 android:title="@string/date">
diff --git a/app/src/main/res/xml/preferences_user_interface.xml b/app/src/main/res/xml/preferences_user_interface.xml
index 455838048..1d970a5f7 100644
--- a/app/src/main/res/xml/preferences_user_interface.xml
+++ b/app/src/main/res/xml/preferences_user_interface.xml
@@ -32,14 +32,6 @@
                 android:summary="@string/pref_nav_drawer_feed_counter_sum"
                 android:defaultValue="0"
                 app:useStockLayout="true"/>
-        <ListPreference
-                android:entryValues="@array/nav_queue_sort_values"
-                android:entries="@array/nav_queue_sort_options"
-                android:title="@string/pref_queue_sort_title"
-                android:key="prefQueueSortOrder"
-                android:summary="@string/pref_queue_sort_sum"
-                android:defaultValue="MANUALLY"
-                app:useStockLayout="true"/>
     </PreferenceCategory>
     <PreferenceCategory android:title="@string/external_elements">
         <SwitchPreference
diff --git a/core/src/main/java/de/danoeh/antennapod/core/preferences/UserPreferences.java b/core/src/main/java/de/danoeh/antennapod/core/preferences/UserPreferences.java
index 9348ca807..2ce7f7835 100644
--- a/core/src/main/java/de/danoeh/antennapod/core/preferences/UserPreferences.java
+++ b/core/src/main/java/de/danoeh/antennapod/core/preferences/UserPreferences.java
@@ -493,7 +493,7 @@ public class UserPreferences {
 
     public static boolean isQueueLocked() {
         return prefs.getBoolean(PREF_QUEUE_LOCKED, false)
-                || !isQueueSortedManually();
+                || isQueueSortedAutomatically();
     }
 
     public static void setFastForwardSecs(int secs) {
@@ -883,6 +883,12 @@ public class UserPreferences {
         return parseQueueSortOrder(sortOrderStr);
     }
 
+    public static void setQueueSortOrder(QueueSortOrder queueSortOrder) {
+        prefs.edit()
+                .putString(PREF_QUEUE_SORT_ORDER, queueSortOrder.name())
+                .apply();
+    }
+
     public static QueueSortOrder parseQueueSortOrder(String value) {
         try {
             return QueueSortOrder.valueOf(value);
@@ -892,8 +898,8 @@ public class UserPreferences {
         }
     }
 
-    public static boolean isQueueSortedManually() {
+    public static boolean isQueueSortedAutomatically() {
         QueueSortOrder sortedOrder = getQueueSortOrder();
-        return sortedOrder == QueueSortOrder.MANUALLY;
+        return sortedOrder != QueueSortOrder.MANUALLY;
     }
 }
diff --git a/core/src/main/java/de/danoeh/antennapod/core/storage/DBWriter.java b/core/src/main/java/de/danoeh/antennapod/core/storage/DBWriter.java
index 2de811788..78812c234 100644
--- a/core/src/main/java/de/danoeh/antennapod/core/storage/DBWriter.java
+++ b/core/src/main/java/de/danoeh/antennapod/core/storage/DBWriter.java
@@ -410,7 +410,7 @@ public class DBWriter {
      * @param events Replaces the events by a single SORT event if the list has to be sorted automatically.
      */
     private static void applySortOrder(List<FeedItem> queue, List<QueueEvent> events) {
-        if (UserPreferences.isQueueSortedManually()) {
+        if (!UserPreferences.isQueueSortedAutomatically()) {
             // automatic sort order is disabled, don't change anything
             return;
         }
diff --git a/core/src/main/java/de/danoeh/antennapod/core/util/QueueSorter.java b/core/src/main/java/de/danoeh/antennapod/core/util/QueueSorter.java
index 8bc377ffa..56402f940 100644
--- a/core/src/main/java/de/danoeh/antennapod/core/util/QueueSorter.java
+++ b/core/src/main/java/de/danoeh/antennapod/core/util/QueueSorter.java
@@ -149,6 +149,38 @@ public class QueueSorter {
         }
     }
 
+    /**
+     * Converts a Rule value to its corresponding QueueSortOrder value.
+     *
+     * @param rule Rule value.
+     * @return QueueSortOrder value corresponding to the given Rule value. <code>null</code> if the Rule value is unsupported or <code>null</code>.
+     */
+    public static UserPreferences.QueueSortOrder rule2QueueSortOrder(Rule rule) {
+        if (rule == null) {
+            return null;
+        }
+        switch (rule) {
+            case EPISODE_TITLE_ASC:
+                return UserPreferences.QueueSortOrder.EPISODE_TITLE_A_Z;
+            case EPISODE_TITLE_DESC:
+                return UserPreferences.QueueSortOrder.EPISODE_TITLE_Z_A;
+            case DATE_ASC:
+                return UserPreferences.QueueSortOrder.DATE_OLD_NEW;
+            case DATE_DESC:
+                return UserPreferences.QueueSortOrder.DATE_NEW_OLD;
+            case DURATION_ASC:
+                return UserPreferences.QueueSortOrder.DURATION_SHORT_LONG;
+            case DURATION_DESC:
+                return UserPreferences.QueueSortOrder.DURATION_LONG_SHORT;
+            case FEED_TITLE_ASC:
+                return UserPreferences.QueueSortOrder.FEED_TITLE_A_Z;
+            case FEED_TITLE_DESC:
+                return UserPreferences.QueueSortOrder.FEED_TITLE_Z_A;
+            default:
+                return null;
+        }
+    }
+
     /**
      * Implements a reordering by pubdate that avoids consecutive episodes from the same feed in
      * the queue.
diff --git a/core/src/main/res/values-de/strings.xml b/core/src/main/res/values-de/strings.xml
index a5ceaab57..449d8b283 100644
--- a/core/src/main/res/values-de/strings.xml
+++ b/core/src/main/res/values-de/strings.xml
@@ -276,6 +276,7 @@
   <string name="move_to_top_label">Zum Anfang verschieben</string>
   <string name="move_to_bottom_label">Zum Ende verschieben</string>
   <string name="sort">Sortieren</string>
+  <string name="sort_automatically">Automatisch sortieren</string>
   <string name="date">Datum</string>
   <string name="duration">Dauer</string>
   <string name="episode_title">Episodentitel</string>
@@ -416,8 +417,6 @@
   <string name="pref_nav_drawer_feed_order_sum">Ändere die Reihenfolge deiner Abonnements</string>
   <string name="pref_nav_drawer_feed_counter_title">Abonnement-Zähler einstellen</string>
   <string name="pref_nav_drawer_feed_counter_sum">Ändere die durch den Abonnementszähler angezeigten Informationen. Betrifft auch die Sortierung der Abonnements wenn \"Reihenfolge der Abonnements\" auf \"Zähler\" gesetzt ist.</string>
-  <string name="pref_queue_sort_title">Sortierung der Abspielliste einstellen</string>
-  <string name="pref_queue_sort_sum">Ändere die Sortierreihenfolge der Episoden in der Abspielliste.</string>
   <string name="pref_set_theme_sum">Ändere das Aussehen von AntennaPod.</string>
   <string name="pref_automatic_download_title">Automatisches Herunterladen</string>
   <string name="pref_automatic_download_sum">Konfiguriere das automatische Herunterladen von Episoden.</string>
@@ -690,11 +689,6 @@
   <string name="sort_date_old_new">Datum (alt \u2192 neu)</string>
   <string name="sort_duration_short_long">Dauer (kurz \u2192 lang)</string>
   <string name="sort_duration_long_short">Dauer (lang \u2192 kurz)</string>
-  <string name="sort_episode_title_a_z">Episodentitel (A \u2192 Z)</string>
-  <string name="sort_episode_title_z_a">Episodentitel (Z \u2192 A)</string>
-  <string name="sort_feed_title_a_z">Podcasttitel (A \u2192 Z)</string>
-  <string name="sort_feed_title_z_a">Podcasttitel (Z \u2192 A)</string>
-  <string name="sort_manually">Manuell</string>
   <!--Rating dialog-->
   <string name="rating_title">Gefällt dir AntennaPod?</string>
   <string name="rating_message">Wir würden uns freuen, wenn du dir kurz die Zeit nimmst, AntennaPod zu bewerten.</string>
diff --git a/core/src/main/res/values/arrays.xml b/core/src/main/res/values/arrays.xml
index d5df4f646..39d1c0a94 100644
--- a/core/src/main/res/values/arrays.xml
+++ b/core/src/main/res/values/arrays.xml
@@ -187,29 +187,6 @@
         <item>3</item>
     </string-array>
 
-    <string-array name="nav_queue_sort_options">
-        <item>@string/sort_manually</item>
-        <item>@string/sort_date_new_old</item>
-        <item>@string/sort_date_old_new</item>
-        <item>@string/sort_duration_short_long</item>
-        <item>@string/sort_duration_long_short</item>
-        <item>@string/sort_episode_title_a_z</item>
-        <item>@string/sort_episode_title_z_a</item>
-        <item>@string/sort_feed_title_a_z</item>
-        <item>@string/sort_feed_title_z_a</item>
-    </string-array>
-    <string-array name="nav_queue_sort_values">
-        <item>MANUALLY</item>
-        <item>DATE_NEW_OLD</item>
-        <item>DATE_OLD_NEW</item>
-        <item>DURATION_SHORT_LONG</item>
-        <item>DURATION_LONG_SHORT</item>
-        <item>EPISODE_TITLE_A_Z</item>
-        <item>EPISODE_TITLE_Z_A</item>
-        <item>FEED_TITLE_A_Z</item>
-        <item>FEED_TITLE_Z_A</item>
-    </string-array>
-
     <string-array name="nav_drawer_feed_counter_options">
         <item>@string/drawer_feed_counter_new_unplayed</item>
         <item>@string/drawer_feed_counter_new</item>
diff --git a/core/src/main/res/values/strings.xml b/core/src/main/res/values/strings.xml
index 9d64cf549..b32bd60df 100644
--- a/core/src/main/res/values/strings.xml
+++ b/core/src/main/res/values/strings.xml
@@ -294,6 +294,7 @@
     <string name="move_to_top_label">Move to top</string>
     <string name="move_to_bottom_label">Move to bottom</string>
     <string name="sort">Sort</string>
+    <string name="sort_automatically">Keep sorted</string>
     <string name="date">Date</string>
     <string name="duration">Duration</string>
     <string name="episode_title">Episode title</string>
@@ -401,8 +402,6 @@
     <string name="pref_nav_drawer_feed_order_sum">Change the order of your subscriptions</string>
     <string name="pref_nav_drawer_feed_counter_title">Set Subscription Counter</string>
     <string name="pref_nav_drawer_feed_counter_sum">Change the information displayed by the subscription counter. Also affects the sorting of subscriptions if \'Subscription Order\' is set to \'Counter\'.</string>
-    <string name="pref_queue_sort_title">Set Queue Sort Order</string>
-    <string name="pref_queue_sort_sum">Change the sort order of the episodes in the queue.</string>
     <string name="pref_set_theme_sum">Change the appearance of AntennaPod.</string>
     <string name="pref_automatic_download_title">Automatic Download</string>
     <string name="pref_automatic_download_sum">Configure the automatic download of episodes.</string>
@@ -697,11 +696,6 @@
     <string name="sort_date_old_new">Date (Old \u2192 New)</string>
     <string name="sort_duration_short_long">Duration (Short \u2192 Long)</string>
     <string name="sort_duration_long_short">Duration (Long \u2192 Short)</string>
-    <string name="sort_episode_title_a_z">Episode title (A \u2192 Z)</string>
-    <string name="sort_episode_title_z_a">Episode title (Z \u2192 A)</string>
-    <string name="sort_feed_title_a_z">Podcast title (A \u2192 Z)</string>
-    <string name="sort_feed_title_z_a">Podcast title (Z \u2192 A)</string>
-    <string name="sort_manually">Manually</string>
 
     <!-- Rating dialog -->
     <string name="rating_title">Like AntennaPod?</string>