diff --git a/runelite-client/src/main/java/net/runelite/client/Notifier.java b/runelite-client/src/main/java/net/runelite/client/Notifier.java
index 5a61dd592a..cdb1d63cfe 100644
--- a/runelite-client/src/main/java/net/runelite/client/Notifier.java
+++ b/runelite-client/src/main/java/net/runelite/client/Notifier.java
@@ -104,6 +104,10 @@ public class Notifier
 
 	private static final String appName = RuneLiteProperties.getTitle();
 
+	private static final File NOTIFICATION_FILE = new File(RuneLite.RUNELITE_DIR, "notification.wav");
+	private static final long CLIP_MTIME_UNLOADED = -2;
+	private static final long CLIP_MTIME_BUILTIN = -1;
+
 	private final Client client;
 	private final RuneLiteConfig runeLiteConfig;
 	private final ClientUI clientUI;
@@ -114,6 +118,8 @@ public class Notifier
 	private final boolean terminalNotifierAvailable;
 	private Instant flashStart;
 	private long mouseLastPressedMillis;
+	private long lastClipMTime = CLIP_MTIME_UNLOADED;
+	private Clip clip = null;
 
 	@Inject
 	private Notifier(
@@ -408,47 +414,73 @@ public class Notifier
 		}
 	}
 
-	private void playCustomSound()
+	private synchronized void playCustomSound()
 	{
-		Clip clip = null;
-
-		// Try to load the user sound from ~/.runelite/notification.wav
-		File file = new File(RuneLite.RUNELITE_DIR, "notification.wav");
-		if (file.exists())
+		long currentMTime = NOTIFICATION_FILE.exists() ? NOTIFICATION_FILE.lastModified() : CLIP_MTIME_BUILTIN;
+		if (clip == null || currentMTime != lastClipMTime || !clip.isOpen())
 		{
+			if (clip != null)
+			{
+				clip.close();
+			}
+
 			try
-			{
-				InputStream fileStream = new BufferedInputStream(new FileInputStream(file));
-				try (AudioInputStream sound = AudioSystem.getAudioInputStream(fileStream))
-				{
-					clip = AudioSystem.getClip();
-					clip.open(sound);
-				}
-			}
-			catch (UnsupportedAudioFileException | IOException | LineUnavailableException e)
-			{
-				clip = null;
-				log.warn("Unable to play notification sound", e);
-			}
-		}
-
-		if (clip == null)
-		{
-			// Otherwise load from the classpath
-			InputStream fileStream = new BufferedInputStream(Notifier.class.getResourceAsStream("notification.wav"));
-			try (AudioInputStream sound = AudioSystem.getAudioInputStream(fileStream))
 			{
 				clip = AudioSystem.getClip();
-				clip.open(sound);
 			}
-			catch (UnsupportedAudioFileException | IOException | LineUnavailableException e)
+			catch (LineUnavailableException e)
 			{
-				log.warn("Unable to play builtin notification sound", e);
+				lastClipMTime = CLIP_MTIME_UNLOADED;
+				log.warn("Unable to play notification", e);
+				Toolkit.getDefaultToolkit().beep();
+				return;
+			}
 
+			lastClipMTime = currentMTime;
+
+			if (!tryLoadNotification())
+			{
 				Toolkit.getDefaultToolkit().beep();
 				return;
 			}
 		}
-		clip.start();
+
+		// Using loop instead of start + setFramePosition prevents a the clip
+		// from not being played sometimes, presumably a race condition in the
+		// underlying line driver
+		clip.loop(1);
+	}
+
+	private boolean tryLoadNotification()
+	{
+		if (NOTIFICATION_FILE.exists())
+		{
+			try
+			{
+				InputStream fileStream = new BufferedInputStream(new FileInputStream(NOTIFICATION_FILE));
+				try (AudioInputStream sound = AudioSystem.getAudioInputStream(fileStream))
+				{
+					clip.open(sound);
+					return true;
+				}
+			}
+			catch (UnsupportedAudioFileException | IOException | LineUnavailableException e)
+			{
+				log.warn("Unable to load notification sound", e);
+			}
+		}
+
+		// Otherwise load from the classpath
+		InputStream fileStream = new BufferedInputStream(Notifier.class.getResourceAsStream("notification.wav"));
+		try (AudioInputStream sound = AudioSystem.getAudioInputStream(fileStream))
+		{
+			clip.open(sound);
+			return true;
+		}
+		catch (UnsupportedAudioFileException | IOException | LineUnavailableException e)
+		{
+			log.warn("Unable to load builtin notification sound", e);
+		}
+		return false;
 	}
 }