diff --git a/src/main/java/com/microsoft/sqlserver/jdbc/KerbAuthentication.java b/src/main/java/com/microsoft/sqlserver/jdbc/KerbAuthentication.java
index b518c45e9..f90e7bea2 100644
--- a/src/main/java/com/microsoft/sqlserver/jdbc/KerbAuthentication.java
+++ b/src/main/java/com/microsoft/sqlserver/jdbc/KerbAuthentication.java
@@ -127,19 +127,33 @@ private void intAuthInit() throws SQLServerException {
             // Kerberos OID
             Oid kerberos = new Oid("1.2.840.113554.1.2.2");
             Subject currentSubject = null;
+            KerbCallback callback = new KerbCallback(con);
             try {
                 AccessControlContext context = AccessController.getContext();
                 currentSubject = Subject.getSubject(context);
                 if (null == currentSubject) {
-                    lc = new LoginContext(CONFIGNAME, new KerbCallback(con));
+                    lc = new LoginContext(CONFIGNAME, callback);
                     lc.login();
                     // per documentation LoginContext will instantiate a new subject.
                     currentSubject = lc.getSubject();
                 }
             }
             catch (LoginException le) {
-                authLogger.fine("Failed to login due to " + le.getClass().getName() + ":" + le.getMessage());
-                con.terminate(SQLServerException.DRIVER_ERROR_NONE, SQLServerException.getErrString("R_integratedAuthenticationFailed"), le);
+                if (authLogger.isLoggable(Level.FINE)) {
+                    authLogger.fine(toString() + "Failed to login using Kerberos due to " + le.getClass().getName() + ":" + le.getMessage());
+                }
+                try {
+                    // Not very clean since it raises an Exception, but we are sure we are cleaning well everything
+                    con.terminate(SQLServerException.DRIVER_ERROR_NONE, SQLServerException.getErrString("R_integratedAuthenticationFailed"), le);
+                } catch (SQLServerException alwaysTriggered) {
+                    String message = String.format("%s due to %s (%s)", alwaysTriggered.getMessage(), le.getClass().getName(), le.getMessage());
+                    if (callback.getUsernameRequested() != null) {
+                        message = String.format("Login failed for Kerberos principal '%s'. %s", callback.getUsernameRequested(), message);
+                    }
+                    // By throwing Exception with LOGON_FAILED -> we avoid looping for connection
+                    // In this case, authentication will never work anyway -> fail fast
+                    throw new SQLServerException(message, alwaysTriggered.getSQLState(), SQLServerException.LOGON_FAILED, le);
+                }
                 return;
             }
 
diff --git a/src/main/java/com/microsoft/sqlserver/jdbc/KerbCallback.java b/src/main/java/com/microsoft/sqlserver/jdbc/KerbCallback.java
index 941d71780..bdb38e3e1 100644
--- a/src/main/java/com/microsoft/sqlserver/jdbc/KerbCallback.java
+++ b/src/main/java/com/microsoft/sqlserver/jdbc/KerbCallback.java
@@ -13,6 +13,7 @@
 public class KerbCallback implements CallbackHandler {
 
     private final SQLServerConnection con;
+    private String usernameRequested = null;
 
     KerbCallback(SQLServerConnection con) {
         this.con = con;
@@ -30,13 +31,22 @@ private static String getAnyOf(Callback callback, Properties properties, String.
                 "Cannot get any of properties: " + Arrays.toString(names) + " from con properties");
     }
 
+    /**
+     * If a name was retrieved By Kerberos, return it.
+     * @return null if callback was not called or username was not provided
+     */
+    public String getUsernameRequested(){
+        return usernameRequested;
+    }
+
     @Override
     public void handle(Callback[] callbacks) throws IOException, UnsupportedCallbackException {
         for (int i = 0; i < callbacks.length; i++) {
             Callback callback = callbacks[i];
             if (callback instanceof NameCallback) {
-                ((NameCallback) callback).setName(getAnyOf(callback, con.activeConnectionProperties,
-                        "user", SQLServerDriverStringProperty.USER.name()));
+                usernameRequested = getAnyOf(callback, con.activeConnectionProperties,
+                                             "user", SQLServerDriverStringProperty.USER.name());
+                ((NameCallback) callback).setName(usernameRequested);
             } else if (callback instanceof PasswordCallback) {
                 String password = getAnyOf(callback, con.activeConnectionProperties,
                         "password", SQLServerDriverStringProperty.PASSWORD.name());
@@ -47,7 +57,5 @@ public void handle(Callback[] callbacks) throws IOException, UnsupportedCallback
                 throw new UnsupportedCallbackException(callback, "Unrecognized Callback type: " + callback.getClass());
             }
         }
-
     }
-
 }