diff --git a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/listener/HistoryWidgetUpdater.java b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/listener/HistoryWidgetUpdater.java
index cef5c49..7ed8920 100644
--- a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/listener/HistoryWidgetUpdater.java
+++ b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/listener/HistoryWidgetUpdater.java
@@ -4,15 +4,21 @@
 import java.util.Arrays;
 import java.util.Collection;
 import java.util.List;
+import java.util.concurrent.atomic.AtomicReference;
 
+import net.pixaurora.kit_tunes.api.event.TrackEndEvent;
+import net.pixaurora.kit_tunes.api.event.TrackStartEvent;
 import net.pixaurora.kit_tunes.api.listener.MusicEventListener;
 import net.pixaurora.kit_tunes.api.music.history.ListenRecord;
 import net.pixaurora.kitten_heart.impl.EventHandling;
 import net.pixaurora.kitten_heart.impl.KitTunes;
 import net.pixaurora.kitten_heart.impl.music.history.ListenHistory;
 import net.pixaurora.kitten_heart.impl.music.progress.PlayingSong;
+import net.pixaurora.kitten_heart.impl.ui.widget.history.HistoryWidget;
 
 public class HistoryWidgetUpdater implements MusicEventListener {
+    public static final AtomicReference<HistoryWidget> LISTENING_WIDGET = new AtomicReference<>();
+
     public static List<ListenRecord> recentTracks(int limit) {
         ArrayList<ListenRecord> recentTracks = new ArrayList<>();
 
@@ -50,4 +56,22 @@ private static Collection<ListenRecord> currentTracks() {
     private static Collection<ListenRecord> pastTracks() {
         return KitTunes.LISTEN_HISTORY.get(ListenHistory::getHistory);
     }
+
+    @Override
+    public void onTrackStart(TrackStartEvent event) {
+        HistoryWidget listeningWidget = LISTENING_WIDGET.get();
+
+        if (listeningWidget != null) {
+            listeningWidget.update();
+        }
+    }
+
+    @Override
+    public void onTrackEnd(TrackEndEvent event) {
+        HistoryWidget listeningWidget = LISTENING_WIDGET.get();
+
+        if (listeningWidget != null) {
+            listeningWidget.update();
+        }
+    }
 }
diff --git a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/screen/music/MusicScreen.java b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/screen/music/MusicScreen.java
index c6f458f..5276b97 100644
--- a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/screen/music/MusicScreen.java
+++ b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/screen/music/MusicScreen.java
@@ -59,7 +59,7 @@ protected Alignment alignmentMethod() {
     protected void firstInit() {
         this.setupMode();
 
-        this.addWidget(new HistoryWidget())
+        this.addWidget(new HistoryWidget(32))
                 .anchor(WidgetAnchor.MIDDLE_LEFT)
                 .at(Point.of(10, 0));
     }
diff --git a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/widget/history/HistoryWidget.java b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/widget/history/HistoryWidget.java
index 5ec5107..ccdbda7 100644
--- a/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/widget/history/HistoryWidget.java
+++ b/projects/kitten-heart/src/main/java/net/pixaurora/kitten_heart/impl/ui/widget/history/HistoryWidget.java
@@ -18,8 +18,6 @@
 import net.pixaurora.kitten_heart.impl.ui.widget.history.HistoryTileSet.Row;
 
 public class HistoryWidget implements Widget {
-    public static final int MAX_ITEMS = 10;
-
     public static final GuiTexture BACKGROUND = GuiTexture
             .of(KitTunes.resource("textures/gui/sprites/widget/music/history/background.png"), Size.of(200, 64));
 
@@ -29,15 +27,26 @@ public class HistoryWidget implements Widget {
             Point.of(0, 21), Size.of(200, 21),
             Point.of(0, 42), Size.of(200, 22));
 
+    private final int verticalPadding;
     private final HistoryTileSet tileSet = TILE_SET;
     private final AtomicReference<View> view;
+    private final AtomicReference<Size> window;
+
+    public HistoryWidget(int verticalPadding) {
+        this.verticalPadding = verticalPadding;
+        this.view = new AtomicReference<>();
+        this.window = new AtomicReference<>();
+    }
 
-    public HistoryWidget() {
-        this.view = new AtomicReference<>(this.initView());
+    @Override
+    public void onWindowUpdate(Size window) {
+        this.window.set(window);
+        this.update();
+        HistoryWidgetUpdater.LISTENING_WIDGET.set(this);
     }
 
     public void update() {
-        this.view.set(this.initView());
+        this.view.set(this.initView(HistoryWidgetUpdater.recentTracks(this.maxItems())));
     }
 
     @Override
@@ -45,12 +54,6 @@ public void draw(GuiDisplay gui, Point mousePos) {
         this.view.get().draw(gui, mousePos);
     }
 
-    public static List<ListenRecord> getMaxAmount() {
-        List<ListenRecord> records = new ArrayList<>();
-
-        return records;
-    }
-
     @Override
     public void onClick(Point mousePos, MouseButton button) {
     }
@@ -65,8 +68,12 @@ public Size size() {
         return this.view.get().size;
     }
 
-    private View initView() {
-        return this.initView(HistoryWidgetUpdater.recentTracks(MAX_ITEMS));
+    private int maxItems() {
+        int middleTilesHeight = this.window.get().height() - this.verticalPadding * 2
+                - (this.tileSet.top().tile().height() + this.tileSet.bottom().tile().height());
+        int middleEntries = middleTilesHeight / this.tileSet.middle().tile().height();
+
+        return middleEntries + 2; // Because the top and bottom were cancelled out before dividing
     }
 
     private View initView(List<ListenRecord> recentMusic) {
diff --git a/projects/kitten-heart/src/main/resources/META-INF/services/net.pixaurora.kit_tunes.api.listener.MusicEventListener b/projects/kitten-heart/src/main/resources/META-INF/services/net.pixaurora.kit_tunes.api.listener.MusicEventListener
index 2c484cc..43297ca 100644
--- a/projects/kitten-heart/src/main/resources/META-INF/services/net.pixaurora.kit_tunes.api.listener.MusicEventListener
+++ b/projects/kitten-heart/src/main/resources/META-INF/services/net.pixaurora.kit_tunes.api.listener.MusicEventListener
@@ -1,2 +1,3 @@
+net.pixaurora.kitten_heart.impl.listener.HistoryWidgetUpdater
 net.pixaurora.kitten_heart.impl.listener.NotificationSendingMusicListener
 net.pixaurora.kitten_heart.impl.listener.ScrobblingMusicListener