diff --git a/client/src/main/java/envoy/client/ui/controller/LoginScene.java b/client/src/main/java/envoy/client/ui/controller/LoginScene.java
index 71e3988..285f3de 100644
--- a/client/src/main/java/envoy/client/ui/controller/LoginScene.java
+++ b/client/src/main/java/envoy/client/ui/controller/LoginScene.java
@@ -46,6 +46,9 @@ public final class LoginScene implements EventListener {
 	@FXML
 	private Button loginButton;
 
+	@FXML
+	private CheckBox cbStaySignedIn;
+
 	@FXML
 	private Button offlineModeButton;
 
@@ -55,7 +58,7 @@ public final class LoginScene implements EventListener {
 	@FXML
 	private ImageView logo;
 
-	private boolean registration = false;
+	private boolean registration;
 
 	private static final Logger			logger	= EnvoyLog.getLogger(LoginScene.class);
 	private static final ClientConfig	config	= ClientConfig.getInstance();
@@ -76,6 +79,7 @@ public final class LoginScene implements EventListener {
 	@FXML
 	private void loginButtonPressed() {
 		final String user = userTextField.getText(), pass = passwordField.getText(), repeatPass = repeatPasswordField.getText();
+		final boolean	requestToken	= cbStaySignedIn.isSelected();
 
 		// Prevent registration with unequal passwords
 		if (registration && !pass.equals(repeatPass)) {
@@ -86,8 +90,8 @@ public final class LoginScene implements EventListener {
 			userTextField.clear();
 		} else {
 			Instant lastSync = Startup.loadLastSync(userTextField.getText());
-			Startup.performHandshake(registration ? LoginCredentials.registration(user, pass, Startup.VERSION, lastSync)
-					: LoginCredentials.login(user, pass, Startup.VERSION, lastSync));
+			Startup.performHandshake(registration ? LoginCredentials.registration(user, pass, requestToken, Startup.VERSION, lastSync)
+					: LoginCredentials.login(user, pass, requestToken, Startup.VERSION, lastSync));
 		}
 	}
 
diff --git a/client/src/main/resources/fxml/LoginScene.fxml b/client/src/main/resources/fxml/LoginScene.fxml
index 1ade0f8..e1316c4 100644
--- a/client/src/main/resources/fxml/LoginScene.fxml
+++ b/client/src/main/resources/fxml/LoginScene.fxml
@@ -2,6 +2,7 @@
 
 <?import javafx.geometry.Insets?>
 <?import javafx.scene.control.Button?>
+<?import javafx.scene.control.CheckBox?>
 <?import javafx.scene.control.Label?>
 <?import javafx.scene.control.PasswordField?>
 <?import javafx.scene.control.TextField?>
@@ -32,9 +33,7 @@
             <Insets bottom="5.0" left="5.0" right="5.0" top="5.0" />
          </padding>
       </Label>
-		<Label alignment="TOP_CENTER" contentDisplay="CENTER"
-			prefHeight="33.0" prefWidth="110.0" text="LOGIN"
-			textAlignment="CENTER">
+		<Label alignment="TOP_CENTER" contentDisplay="CENTER" prefHeight="33.0" prefWidth="110.0" text="LOGIN" textAlignment="CENTER">
 			<font>
 				<Font size="26.0" />
 			</font>
@@ -92,6 +91,11 @@
             <Insets bottom="2.0" left="125.0" right="125.0" top="2.0" />
          </padding>
 				</Button>
+      <CheckBox fx:id="cbStaySignedIn" mnemonicParsing="false" text="Keep me signed in">
+         <VBox.margin>
+            <Insets bottom="10.0" top="10.0" />
+         </VBox.margin>
+      </CheckBox>
       <HBox alignment="CENTER" prefHeight="30.0" prefWidth="200.0">
          <children>
             <Label fx:id="registerTextLabel" text="No account yet?" />
diff --git a/common/src/main/java/envoy/data/LoginCredentials.java b/common/src/main/java/envoy/data/LoginCredentials.java
index 40866ad..e4edd72 100644
--- a/common/src/main/java/envoy/data/LoginCredentials.java
+++ b/common/src/main/java/envoy/data/LoginCredentials.java
@@ -20,16 +20,18 @@ import java.time.Instant;
 public final class LoginCredentials implements Serializable {
 
 	private final String	identifier, password, clientVersion;
-	private final boolean	registration, token;
+	private final boolean	registration, token, requestToken;
 	private final Instant	lastSync;
 
-	private static final long serialVersionUID = 3;
+	private static final long serialVersionUID = 4;
 
-	private LoginCredentials(String identifier, String password, boolean registration, boolean token, String clientVersion, Instant lastSync) {
+	private LoginCredentials(String identifier, String password, boolean registration, boolean token, boolean requestToken, String clientVersion,
+			Instant lastSync) {
 		this.identifier		= identifier;
 		this.password		= password;
 		this.registration	= registration;
 		this.token			= token;
+		this.requestToken	= requestToken;
 		this.clientVersion	= clientVersion;
 		this.lastSync		= lastSync;
 	}
@@ -39,13 +41,14 @@ public final class LoginCredentials implements Serializable {
 	 *
 	 * @param identifier    the identifier of the user
 	 * @param password      the password of the user
+	 * @param requestToken  requests the server to generate an authentication token
 	 * @param clientVersion the version of the client sending these credentials
 	 * @param lastSync      the timestamp of the last synchronization
 	 * @return the created login credentials
 	 * @since Envoy Common v0.2-beta
 	 */
-	public static LoginCredentials login(String identifier, String password, String clientVersion, Instant lastSync) {
-		return new LoginCredentials(identifier, password, false, false, clientVersion, lastSync);
+	public static LoginCredentials login(String identifier, String password, boolean requestToken, String clientVersion, Instant lastSync) {
+		return new LoginCredentials(identifier, password, false, false, requestToken, clientVersion, lastSync);
 	}
 
 	/**
@@ -59,7 +62,7 @@ public final class LoginCredentials implements Serializable {
 	 * @since Envoy Common v0.2-beta
 	 */
 	public static LoginCredentials loginWithToken(String identifier, String token, String clientVersion, Instant lastSync) {
-		return new LoginCredentials(identifier, token, false, true, clientVersion, lastSync);
+		return new LoginCredentials(identifier, token, false, true, false, clientVersion, lastSync);
 	}
 
 	/**
@@ -67,21 +70,23 @@ public final class LoginCredentials implements Serializable {
 	 *
 	 * @param identifier    the identifier of the user
 	 * @param password      the password of the user
+	 * @param requestToken  requests the server to generate an authentication token
 	 * @param clientVersion the version of the client sending these credentials
 	 * @param lastSync      the timestamp of the last synchronization
 	 * @return the created login credentials
 	 * @since Envoy Common v0.2-beta
 	 */
-	public static LoginCredentials registration(String identifier, String password, String clientVersion, Instant lastSync) {
-		return new LoginCredentials(identifier, password, true, false, clientVersion, lastSync);
+	public static LoginCredentials registration(String identifier, String password, boolean requestToken, String clientVersion, Instant lastSync) {
+		return new LoginCredentials(identifier, password, true, false, requestToken, clientVersion, lastSync);
 	}
 
 	@Override
 	public String toString() {
-		return String.format("LoginCredentials[identifier=%s,registration=%b,token=%b,clientVersion=%s,lastSync=%s]",
+		return String.format("LoginCredentials[identifier=%s,registration=%b,token=%b,requestToken=%b,clientVersion=%s,lastSync=%s]",
 				identifier,
 				registration,
 				token,
+				requestToken,
 				clientVersion,
 				lastSync);
 	}
@@ -112,6 +117,12 @@ public final class LoginCredentials implements Serializable {
 	 */
 	public boolean usesToken() { return token; }
 
+	/**
+	 * @return {@code true} if the server should generate a new authentication token
+	 * @since Envoy Common v0.2-beta
+	 */
+	public boolean requestToken() { return requestToken; }
+
 	/**
 	 * @return the version of the client sending these credentials
 	 * @since Envoy Common v0.1-beta
@@ -119,7 +130,7 @@ public final class LoginCredentials implements Serializable {
 	public String getClientVersion() { return clientVersion; }
 
 	/**
-	 * @return the time stamp of the last synchronization
+	 * @return the timestamp of the last synchronization
 	 * @since Envoy Common v0.2-beta
 	 */
 	public Instant getLastSync() { return lastSync; }