diff --git a/src/main/java/envoy/client/Client.java b/src/main/java/envoy/client/Client.java
index ed2ff22..f56cfe4 100644
--- a/src/main/java/envoy/client/Client.java
+++ b/src/main/java/envoy/client/Client.java
@@ -1,6 +1,5 @@
 package envoy.client;
 
-import java.time.Instant;
 import javax.ws.rs.client.ClientBuilder;
 import javax.ws.rs.client.Entity;
 import javax.ws.rs.client.WebTarget;
@@ -8,11 +7,7 @@ import javax.ws.rs.core.Response;
 import javax.xml.bind.JAXBContext;
 import javax.xml.bind.JAXBException;
 import javax.xml.bind.Marshaller;
-import javax.xml.datatype.DatatypeConfigurationException;
-import javax.xml.datatype.DatatypeFactory;
 
-import envoy.schema.Message;
-import envoy.schema.Message.Metadata.MessageState;
 import envoy.schema.ObjectFactory;
 import envoy.schema.Sync;
 import envoy.schema.User;
diff --git a/src/main/java/envoy/client/LocalDB.java b/src/main/java/envoy/client/LocalDB.java
index fb69a94..e0ff7c1 100644
--- a/src/main/java/envoy/client/LocalDB.java
+++ b/src/main/java/envoy/client/LocalDB.java
@@ -10,18 +10,15 @@ import java.time.Instant;
 import java.util.ArrayList;
 import java.util.List;
 
-import javax.xml.bind.JAXBContext;
-import javax.xml.bind.JAXBException;
-import javax.xml.bind.Marshaller;
 import javax.xml.datatype.DatatypeConfigurationException;
 import javax.xml.datatype.DatatypeFactory;
 
 import envoy.exception.EnvoyException;
 import envoy.schema.Message;
-import envoy.schema.User;
 import envoy.schema.Message.Metadata.MessageState;
 import envoy.schema.ObjectFactory;
 import envoy.schema.Sync;
+import envoy.schema.User;
 
 /**
  * Project: <strong>envoy-client</strong><br>
@@ -29,6 +26,7 @@ import envoy.schema.Sync;
  * Created: <strong>27.10.2019</strong><br>
  *
  * @author Kai S. K. Engelbart
+ * @author Maximilian K&auml;fer
  * @since Envoy v0.1-alpha
  */
 public class LocalDB {
@@ -130,27 +128,26 @@ public class LocalDB {
 
 		return message;
 	}
-	
+
 	private Sync	unreadMessagesSync	= objectFactory.createSync();
 	public Sync		sync				= objectFactory.createSync();
 	public Sync		readMessages		= objectFactory.createSync();
-	
-	public Sync fillSync(long userId) {
-			
-			addWaitingMessagesToSync();
 
-			getSentStateMessagesFromLocalDB();
-			for (int i = 0; i < readMessages.getMessages().size(); i++) {
-				sync.getMessages().add(readMessages.getMessages().get(i));
-			}
-			readMessages.getMessages().clear();
-			
+	public Sync fillSync(long userId) {
+
+		addWaitingMessagesToSync();
+
+		getSentStateMessagesFromLocalDB();
+		for (int i = 0; i < readMessages.getMessages().size(); i++) {
+			sync.getMessages().add(readMessages.getMessages().get(i));
+		}
+		readMessages.getMessages().clear();
 
 		System.out.println(sync.getMessages().size());
 		return sync;
 	}
-	
-	public void applySync (Sync returnSync) {
+
+	public void applySync(Sync returnSync) {
 		for (int i = 0; i < returnSync.getMessages().size(); i++) {
 			if (returnSync.getMessages().get(i).getMetadata().getMessageId() != 0
 					&& returnSync.getMessages().get(i).getMetadata().getState() == MessageState.SENT) {
@@ -167,37 +164,34 @@ public class LocalDB {
 							.getMetadata()
 							.setState(returnSync.getMessages().get(j).getMetadata().getState());
 					}
-	
+
 				}
-	
+
 			}
 			if (returnSync.getMessages().get(i).getMetadata().getMessageId() != 0
 					&& returnSync.getMessages().get(i).getMetadata().getSender() != 0
 					&& returnSync.getMessages().get(i).getMetadata().getState() == MessageState.RECEIVED) {
 				// these are the unread Messages from the server
 				unreadMessagesSync.getMessages().add(returnSync.getMessages().get(i));
-	
+
 			}
-	
+
 			if (returnSync.getMessages().get(i).getMetadata().getMessageId() != 0
 					&& returnSync.getMessages().get(i).getMetadata().getSender() == 0
 					&& returnSync.getMessages().get(i).getMetadata().getState() == MessageState.RECEIVED) {
 				// Update Messages in localDB to state RECEIVED
 				for (int j = 0; j < getChats().size(); j++) {
-					if (getChats().get(j).getRecipient().getID() == returnSync.getMessages()
-						.get(i)
-						.getMetadata()
-						.getRecipient()) {
+					if (getChats().get(j)
+						.getRecipient()
+						.getID() == returnSync.getMessages().get(i).getMetadata().getRecipient()) {
 						for (int k = 0; k < getChats().get(j).getModel().getSize(); k++) {
-							if (getChats()
-								.get(j)
-								.getModel()
-								.get(k)
+							if (getChats().get(j).getModel().get(k).getMetadata().getMessageId() == returnSync
+								.getMessages()
+								.get(i)
 								.getMetadata()
-								.getMessageId() == returnSync.getMessages().get(i).getMetadata().getMessageId()) {
+								.getMessageId()) {
 								// Update Message in LocalDB
-								getChats()
-									.get(j)
+								getChats().get(j)
 									.getModel()
 									.get(k)
 									.getMetadata()
@@ -206,50 +200,40 @@ public class LocalDB {
 						}
 					}
 				}
-	
+
 			}
-	
+
 			if (returnSync.getMessages().get(i).getMetadata().getMessageId() != 0
 					&& returnSync.getMessages().get(i).getMetadata().getState() == MessageState.READ) {
 				// Update local Messages to state READ
-				System.out
-					.println("Message with ID: " + returnSync.getMessages().get(i).getMetadata().getMessageId()
-							+ "was initialized to be set to READ in localDB.");
+				System.out.println("Message with ID: " + returnSync.getMessages().get(i).getMetadata().getMessageId()
+						+ "was initialized to be set to READ in localDB.");
 				for (int j = 0; j < getChats().size(); j++) {
-					if (getChats().get(j).getRecipient().getID() == returnSync.getMessages()
-						.get(i)
-						.getMetadata()
-						.getRecipient()) {
-						System.out.println(
-								"Chat with: " + getChats().get(j).getRecipient().getID() + "was selected.");
+					if (getChats().get(j)
+						.getRecipient()
+						.getID() == returnSync.getMessages().get(i).getMetadata().getRecipient()) {
+						System.out.println("Chat with: " + getChats().get(j).getRecipient().getID() + "was selected.");
 						for (int k = 0; k < getChats().get(j).getModel().getSize(); k++) {
-							if (getChats()
-								.get(j)
-								.getModel()
-								.get(k)
+							if (getChats().get(j).getModel().get(k).getMetadata().getMessageId() == returnSync
+								.getMessages()
+								.get(i)
 								.getMetadata()
-								.getMessageId() == returnSync.getMessages().get(i).getMetadata().getMessageId()) {
+								.getMessageId()) {
 								System.out.println("Message with ID: "
 										+ getChats().get(j).getModel().get(k).getMetadata().getMessageId()
 										+ "was selected.");
-								getChats()
-									.get(j)
+								getChats().get(j)
 									.getModel()
 									.get(k)
 									.getMetadata()
 									.setState(returnSync.getMessages().get(i).getMetadata().getState());
-								System.out.println("Message State is now: " + getChats()
-									.get(j)
-									.getModel()
-									.get(k)
-									.getMetadata()
-									.getState()
-									.toString());
+								System.out.println("Message State is now: "
+										+ getChats().get(j).getModel().get(k).getMetadata().getState().toString());
 							}
 						}
 					}
 				}
-	
+
 			}
 		}
 
@@ -257,13 +241,13 @@ public class LocalDB {
 		for (int j = 0; j < returnSync.getUsers().size(); j++) {
 			for (int k = 0; k < getChats().size(); k++) {
 				if (getChats().get(k).getRecipient().getID() == returnSync.getUsers().get(j).getID()) {
-	
+
 					getChats().get(k).getRecipient().setStatus(returnSync.getUsers().get(j).getStatus());
 					System.out.println(getChats().get(k).getRecipient().getStatus().toString());
 				}
 			}
 		}
-	
+
 		sync.getMessages().clear();
 		sync.getUsers().clear();
 
@@ -296,10 +280,9 @@ public class LocalDB {
 		Sync unreadMessages = unreadMessagesSync;
 		for (int i = 0; i < unreadMessages.getMessages().size(); i++)
 			for (int j = 0; j < getChats().size(); j++)
-				if (getChats().get(j).getRecipient().getID() == unreadMessages.getMessages()
-					.get(i)
-					.getMetadata()
-					.getSender()) {
+				if (getChats().get(j)
+					.getRecipient()
+					.getID() == unreadMessages.getMessages().get(i).getMetadata().getSender()) {
 					getChats().get(j).appendMessage(unreadMessages.getMessages().get(i));
 				}
 	}
@@ -330,14 +313,12 @@ public class LocalDB {
 	 * @since Envoy v0.1-alpha
 	 */
 	public void setMessagesToRead(Chat currentChat) {
-		for (int j = 0; j < currentChat.getModel().getSize(); j++) {
-			if (currentChat.getModel().get(j).getMetadata().getRecipient() != currentChat.getRecipient().getID()) {
-				if (currentChat.getModel().get(j).getMetadata().getState() == MessageState.RECEIVED) {
-					currentChat.getModel().get(j).getMetadata().setState(MessageState.READ);
-					readMessages.getMessages().add(currentChat.getModel().get(j));
-				}
-			}
-		}
+		for (int i = currentChat.getModel().size() - 1; i >= 0; --i)
+			if (currentChat.getModel().get(i).getMetadata().getRecipient() != currentChat.getRecipient().getID())
+				if (currentChat.getModel().get(i).getMetadata().getState() == MessageState.RECEIVED) {
+					currentChat.getModel().get(i).getMetadata().setState(MessageState.READ);
+					readMessages.getMessages().add(currentChat.getModel().get(i));
+				} else break;
 	}
 
 	/**
@@ -373,7 +354,7 @@ public class LocalDB {
 	 * @since Envoy v0.1-alpha
 	 */
 	public void clearUnreadMessagesSync() { unreadMessagesSync.getMessages().clear(); }
-	
+
 	/**
 	 * @return all saves {@link Chat} objects that list the client user as the
 	 *         sender
diff --git a/src/main/java/envoy/client/ui/ChatWindow.java b/src/main/java/envoy/client/ui/ChatWindow.java
index 545715e..c6e8c37 100644
--- a/src/main/java/envoy/client/ui/ChatWindow.java
+++ b/src/main/java/envoy/client/ui/ChatWindow.java
@@ -205,6 +205,9 @@ public class ChatWindow extends JFrame {
 					.findFirst()
 					.get();
 
+				// Set all unread messages in the chat to read
+				if (currentChat != null) { localDB.setMessagesToRead(currentChat); }
+
 				client.setRecipient(user);
 
 				textPane.setText(currentChat.getRecipient().getName());
@@ -265,8 +268,6 @@ public class ChatWindow extends JFrame {
 	 */
 	private void startSyncThread(int timeout) {
 		new Timer(timeout, (evt) -> {
-			if (currentChat != null) { localDB.setMessagesToRead(currentChat); }
-
 			new Thread(() -> {
 
 				// Synchronize