diff --git a/command/src/com/mirth/connect/cli/CommandLineInterface.java b/command/src/com/mirth/connect/cli/CommandLineInterface.java
index 1e785ab14..e1582bfaa 100644
--- a/command/src/com/mirth/connect/cli/CommandLineInterface.java
+++ b/command/src/com/mirth/connect/cli/CommandLineInterface.java
@@ -58,6 +58,7 @@
 import com.mirth.connect.client.core.PaginatedEventList;
 import com.mirth.connect.client.core.PaginatedMessageList;
 import com.mirth.connect.client.core.PropertiesConfigurationUtil;
+import com.mirth.connect.client.core.UnauthorizedException;
 import com.mirth.connect.donkey.model.channel.DeployedState;
 import com.mirth.connect.donkey.model.message.ContentType;
 import com.mirth.connect.donkey.model.message.Message;
@@ -179,11 +180,22 @@ private void runShell(String server, String user, String password, String script
             client = new Client(server);
             this.debug = debug;
 
-            LoginStatus loginStatus = client.login(user, password);
-
-            if (loginStatus.getStatus() != LoginStatus.Status.SUCCESS) {
-                error("Could not login to server.", null);
-                return;
+            LoginStatus loginStatus = null;
+            try {
+                loginStatus = client.login(user, password);
+            } catch (UnauthorizedException ex) {
+                if (ex.getResponse() instanceof LoginStatus status && status.isSuccess()) {
+                    loginStatus = status;
+                }
+            }
+            finally {
+                if (loginStatus == null) {
+                    error("Could not login to server");
+                    System.exit(70);
+                }
+                else if (!loginStatus.isSuccess()) {
+                    error("Could not login to server. Please check your username and password and try again.", null);                    System.exit(77);
+                }
             }
 
             String serverVersion = client.getVersion();